All Episodes

May 2, 2026 • 56 mins
The Wishing Well's Terrie Dean and Harry Reif deliver a true master class in group travel.

From family reunions and multi‑generational vacations to corporate trips, cruises, and escorted tours, this episode breaks down how to plan successful group travel without stress.

Learn how to define your group, choose the right destination and timing, manage budgets and expectations, avoid common mistakes, and understand the critical role of a group leader. Whether you’re the Pied Piper organizing the trip or someone considering joining one, this episode is packed with expert insight, real-world stories, and practical travel advice from the Wishing Well travel professionals.
Listen
Watch
Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
This is a Lifeless Ordinary, the travel show and podcasts
from your friends at the wishing Well two forty three
f Avenue in Harsmer and online at the wishing Well
dot biz. The wishing Well is your ultimate luxury concierge
travel agency and A Lifeless Ordinary is a travel show
and podcasts hosted by Terry Dean, bringing her over forty
years of experience in the travel industry to help guide

(00:21):
you to great experiences in your travel, whether it be
around the block, around the country, or around the world.
Let's bring in Terry Dean and say, hello, Chris.

Speaker 2 (00:29):
This is a beautiful Saturday.

Speaker 1 (00:31):
It is well, every Saturday is a beautiful Saturday. I agree,
because we get to sit and talk about travel.

Speaker 2 (00:37):
Indeed we do.

Speaker 1 (00:38):
We just close our eyes and we picture all these
wonderful places that you describe. And so even when it's
a rainy Saturday or a cold and snowy Saturday, whatever
Mother Nature it.

Speaker 2 (00:49):
Does it, it's always a beautiful Saturday here on a
Lifeless Ordinary, always always, always, always so happy weekend.

Speaker 1 (00:55):
Thank you. Yeah.

Speaker 3 (00:56):
Ed.

Speaker 1 (00:56):
Harry is with us as well.

Speaker 3 (00:58):
Talking about one of my favorite topics, how can you
not be happy and have it be a good Saturday.

Speaker 1 (01:03):
What's that imagination time? What do we travel? Okay?

Speaker 3 (01:08):
And a life less ordinary for sure. I think if
people haven't picked up on that's what we do every Saturday,
they're just not listening.

Speaker 1 (01:15):
Chris Well, we want to welcome people who have discovered
us today, brand new listeners. Maybe a friend has directed
you towards this time slot. Here every Saturday morning at
just after ten o'clock, we sit down Terry Dean Harry
Rife from the Wishing Well, and my name's Chris Carmichael.
If you knew the show, and we sit down, we
talk travel and there's always a topic something specific that

(01:39):
we get into. My favorite shows are when we get
to talk about answering questions that we all have, which
is kind of every show, and last week we talked
about impact travel. Sometimes we'll pick a specific place in
the world and give you some of those behind the
behind the door secrets. I know when we talked about

(02:00):
I guess you talked about those speakeasiess right, you have
the context so that you have the secret word when
you knock on the door.

Speaker 2 (02:06):
We do. We're not just kidding when we say we
have magic wands at the Wishing well, we know where
the best secrets are buried, so we know how to
find them. We know how to tell you where they are,
and I'm always happy to do that.

Speaker 1 (02:18):
And one of the topics that we've talked about in
previous episodes that we're going to delve into today is
group travel.

Speaker 2 (02:24):
We are, yeah, and that's sort of a big mystery
for people, big question Mark, And I loved what you
said about when we take the opportunity here on Life
Less Ordinary to answer questions that people have. The whole
reason that this topic came to Fruition today is because
I've been dealing with a lot of that lately, MultiGen families,

(02:47):
different friend groups and that kind of thing. But this
is a topic that sometimes gives people a little bit
of heartburn because they're not exactly sure how to go
about it, what the what the answers are to the
questions that they have.

Speaker 1 (03:01):
I'll tell you when I book travel, it's just me
and my wife that gives me heart burn. I can't
imagine trying to coordinate amongst you know, the larger family group.

Speaker 2 (03:11):
And it's a little different process it is, and a
whole lot more moving parts come into play. And before
we move into that though. It was real interesting Chris
this week at the Wishing Well. I had such a
great week at the wish It was trying, you know,
it was very, very busy. We're in our busy season

(03:31):
right now, but it was funny. We all kind of
met together yesterday and we sat down as a group
and just talked about what hearts of gratitude that we have.
And I think it's always good to kind of share
that level of gratitude with our listeners, with our staff,
and with our customers. We certainly, Harry and I both

(03:53):
are very very honored and humbled that every Saturday you come,
you join us here on a lifeless ordinary, and you
honor us by letting us come into your homes and
impart our wisdom and our knowledge and our travel experiences
to you. So thank you, thank you, thank you for that.
It is another Saturday and we are here with a

(04:15):
lifeless ordinary, and we are going to have a master
class in group travel today.

Speaker 1 (04:22):
They're gonna be a exciting show. Like I said, we've
talked about group travel before, but to dig this deep
into it. You say masterclass, what exactly does that mean.

Speaker 2 (04:33):
A lot of things really, And we're going to get
started by talking about we're going to skim the surface
and then you're right, Chris, We're going to go down
deep into the core of this subject a little bit.
And actually this topic might even bleed into future episodes.
So if we don't finish everything that we wanted to
talk about today, no worries. We're going to continue this

(04:54):
topic as we can and as we move through this,
because I fully want you guys who are listening to
us to be able to wrap your arms around what
we're talking about. It's not an easy topic to understand.

Speaker 1 (05:06):
So we say group travel are and maybe all of
these fall into that umbrella. Are we talking about a
family reunion getaway? Are we talking about corporate group travel?
You're shaking your head yes on both of these.

Speaker 2 (05:23):
That's all of that.

Speaker 1 (05:26):
We as whoever. The consumer is the person who's coming
into the wishing well saying Terry help. They have sat down,
had a conversation either with their loved ones they or
maybe they haven't yet, and they're trying to get information
so they can have that conversation. You said, it can
be very overwhelming. It I can, and I'm imagining that

(05:48):
for the person who draws the short straw and has
to try to organize all that. The piper is looking
for your help.

Speaker 2 (05:57):
Yeah, and I'll tell you, Chris, there's a moment in
travel that changes everything. It's not the destination, it's not
the hotel, it's not even the view from your balcony.
It's the moment you look around and you realize you
didn't get there alone and you came there with your people.

(06:17):
You know, that's that defining moment, and suddenly your experience
is a whole lot richer. Things sound different, they're more meaningful,
far far far more memorable. And this morning we're going
to talk about one of the most powerful and most
misunderstood ways to travel, I think, and that is we've

(06:40):
already touched on that group travel, and it's not just
why you should consider it, but really our show today
is about how to do it right. Because when group
travel works, it's extraordinary, it really is, and when it doesn't,
it's something that people almost quietly, sometimes very loudly, say
they'll never do again. So this morning I'm going to

(07:03):
walk you through exactly how to build a successful travel group,
from the very first idea to wheels up to coming
home with relationships even stronger than the ones you think
you left.

Speaker 3 (07:16):
Yeah, And I think it's important for listeners to know
Terry and Chris that at the Wishing Well we have
a lot of groups every year, maybe a dozen more
groups every year, for sure. It doesn't easily and some
are escorted by us, you know, trained hosts at the
Wishing Well. I do a lot of them. Others are
escorted by key people that are actually within the group,

(07:37):
and we coach and train and support those people. So
there's lots of ways to do group travel. And what
I'm hoping we accomplished this morning is we're going to
walk listeners through exactly how to build a successful travel group.

Speaker 2 (07:53):
Yeah, and then I'm going to break this down into
some segments so that it's a little bit easier to
digest and understand exactly where we're going. So let's jump
in and get started with this. What do you say?
And we're going to talk about my first segment, which
is why group travel is having a moment, because it is.

(08:14):
It's not new, but the way we're doing it today
has really changed dramatically from you know, forty eight years
ago when I entered this industry. It's really not the
same anymore.

Speaker 1 (08:24):
You have not been doing this this long. Yeah, you're
not old enough for long.

Speaker 2 (08:29):
Thank you, Chris. You get some extra cake next time
I come.

Speaker 1 (08:32):
Carrie, I believe could have been doing it that long,
not you.

Speaker 3 (08:36):
Oh wow.

Speaker 2 (08:38):
But what we're seeing is, and we've talked about that
a lot. Here, we're seeing a lot of multi generational
families traveling together. We're seeing friends creating some milestone trips.
I've done a lot of these this year. We're doing
like celebratory birthdays, milestone birthdays and anniversaries and goodness retirements.
We've got social groups, wine clubs, alumni groups, church groups,

(09:02):
and even I've been reached out to recently just because travel.
You know, they they want to go just because and
when that experience matters more than the occasion. And here's why, Chris,
it's growing so quickly. Number one, You've got those shared
experiences that multiply the joy when you're on a trip.

(09:25):
Travel is emotional. Remember those previous lifeless ordinary episodes that
we've been talking about. How you can feel it, you
can see it. It reminds you of something, you hear,
something you smell of food. All of a sudden, you're
back to your childhood. Travel is emotional and when you
share those emotions, whether it's watching the sun over the

(09:47):
Amalfi Coast you're laughing. If you missed a train in Paris,
that's a whole nother story. It becomes part of your
collective story. Okay. The next thing is you've got access
and value, and group travel often unlocks that. You get
preferred pricing, exclusive excursions, you get private gods, you get

(10:08):
those added amenities like onboard credits or hosted events. You
get a built in community when you are traveling with
a group. And so for a lot of travelers, especially
those who don't want to travel alone, group travel really
removes a lot of the uncertainty and that's where it
hangs people sometimes, you know, even solo travelers, they're like, man,

(10:30):
I don't want to I don't think I want to
go by myself. Group travel sort of is the thing
that overcomes that, and there's always somebody to dine with,
you can explore with, or you just simply share a
glass of wine at the end of the day.

Speaker 3 (10:45):
Yeah, you mentioned solo travelers. There are a lot of
people out there listening, a lot of people that have
traveled with us that come on groups. And I have groups, Chris,
that are composed of solo travelers. So they build this
Terry was talking about, they build their own community. They
have something in common, and it's safe because they're in
a community that are all or mostly solo travelers. So

(11:09):
if you can think about how that makes people feel,
it makes them feel very comfortable, it makes them feel
very connected, and they're in a group, so they're going
to be taken care of.

Speaker 2 (11:20):
So now what I'm going to do, moving into segment
two of this, We're going to call this defining your
group with intention. And this is where a lot of
people get it wrong, Chris. And this is easy to do.
This is easy to misstep on this one.

Speaker 1 (11:35):
I mean, just as you say that, I'm thinking, oh,
there's always that one person in a group that is
like lighting a match and thrown it into a pool
of gasoline.

Speaker 3 (11:45):
Yep.

Speaker 2 (11:45):
And interestingly enough, I dealt with this very situation with
a young man several weeks ago who wanted to start
with a group, and he dealt with a lot of
some of these things that we're talking about day. Because
the mistake that a lot of people make is they
start with let's just see who wants to go okay,

(12:09):
and that sounds friendly, but it's not very strategic. So
instead you want to start with this question, who is
this trip really for? Is it adults only? Is it
families with children? Is that who you're going to target?
Is it going to be kind of an active group?

(12:31):
Are you going to kind of want to do some
hiking and biking and I mean we have tour operators
that specialize in just that. You know, you can bike
all around Italy and Ireland and Scotland and places like that.
Is that the group you want? Or are these guys
going to be the guys who just want to go party,
lay on the beach and just have fun that way?
Or is this going to be a luxury focused group?

(12:53):
You know, do these people really are they interested in
more of a foody, culinary kind of experience or a
why trip or or this is important, are they a
budgets budget conscious group of explorers? Because that's going to
really determine a lot there. The moment you try to
please everybody, though, you're going to dilute the experience. And

(13:17):
that's what's important to note, because your role as the
organizer becomes one thing and one thing only. And this
is again I'm speaking to you. If you want to
be a group leader or pod piper, your role is
one thing, one word, and that is clarity. Okay, You've

(13:38):
got to be clear, and clarity is going to create
the right group.

Speaker 3 (13:43):
Yeah, there's what you're saying, in other words, is there's
got to be a glue. There's got to be something
that binds this group together, and all the things that
you mentioned are potential things that will bind them together.
There's some people don't want to travel with kids adults only.
That's a great, great idea, active travelers. We're gonna be
doing something. We are from eight in the morning until

(14:04):
five at night or ten at night. We're going to
be moving. That's a very different group from the from
the group that says, hey, we want to go shopping
during the day.

Speaker 1 (14:13):
As the organizer, is it also important to try to
make sure you have something for everyone.

Speaker 3 (14:20):
Yeah.

Speaker 2 (14:20):
So, I mean you want to make sure that the
group that you've defined and the group that you've invited
into this oneness experience is of one mind and one accord.
You know. I hear pastors talk about this with their
churches before, and certainly that is true with a group

(14:41):
of whomever are traveling together.

Speaker 3 (14:45):
And you can handle that in a lot of different ways. Chris.
There are groups that I've been on where I've had
the after the morning where we'll do something in commonness
of interest to everybody. In the afternoon, I say, hey,
we've got a couple options. There's some people who want
to go in town and want to walk through the
little stores and look at things. And there's another group
that wants to learn more about the history of that location,

(15:08):
and so they'll go to a museum where the first
group is in the stores and shopping, and we meet
together at dinner. And that's another part of the magic
of a group. At dinner, they come together and they
share what they've learned with each other. And what a
great cohesive way to have a group.

Speaker 2 (15:24):
And I love that you asked that question, because I
know you don't read my notes ahead of time, but
you always ask just the right questions to segue into
the next segment of what I want to talk about, Chris.
So segment three is what we're moving into now, and
it's really step two. It is choosing the right type

(15:44):
of group experience. Okay, so now you've selected maybe where
you want to go, you know, the right people that
you want to go on this experience. Now, the next
thing is selecting the right type of group experience. Not
all group travel is created equal, and this is what

(16:05):
really matters. So option one might be a cruise, okay,
and that's very popular. I'll tell you that for a
lot of our group leaders, people who bring groups to us, that's,
you know, primarily one thing that they like to focus on.

Speaker 1 (16:20):
It seems to me that would be the easy, the
easy choice, because a cruise has something for everybody already
laid out.

Speaker 2 (16:27):
Yeah, it's one of the easiest ways to manage a
group really because you've got built in dining, you've got
structured itineraries. There really is something for everybody, and it's
ideal for multi generational groups and first time group organizers. Plus,
you know, with the right kind of cruise, if your
group wants this, you're in a different port every day

(16:48):
and you travel at night, so it kind of checks
all the boxes, if you will, for a certain kind
of traveler.

Speaker 1 (16:56):
Yeah, I mean, you still want to make sure that
the cruise you're selecting matches your group. If you don't
want to go on a disney cruise. If you don't
want kids to be coming in in your group, you're
spot on them with that, Or you don't want to
go to the Caribbean if everybody in your group has
been begging to go to Alaska.

Speaker 3 (17:11):
And there's way more flavors of cruises. There are river cruises,
there are ocean cruises, there are explorer cruises. So you
have to pick the right cruise type. And we're going
to get into this a little more. Which you got
to pick the right cruise line because even if you
want to do river cruising, there's different styles. If you
go back to the particular group you have and what

(17:32):
that glue is, that will tell us which line, which
cruise line, which cruise operator might be best for that group.

Speaker 1 (17:40):
Can we back up for one second and get a
definition of the group. How many people do I need
to have before it's just my family and it becomes
a group magic question?

Speaker 2 (17:51):
So it's different with different vendors and different providers. Okay,
So for some cruise lines and some in particular that
I'm thinking of right now, you only need five cabins
and that's a group.

Speaker 1 (18:05):
Okay.

Speaker 2 (18:05):
For airlines, in many cases, you need at least ten people,
sometimes twenty for it to be a group. For other
cruise lines, you have to have ten cabins for it
to be a group which is going to be twenty people,
or if you've got singles in there, they'll count those two.
So really the answer to that question, Chris is a

(18:26):
group is defined really primarily by the provider that's going
to be servicing the group. And that's a great question
because you want to know that going in and it
goes back to what.

Speaker 3 (18:37):
I was saying before in terms of choosing the right
provider for a group. That's where I think we have
an advantage as travel professionals. We know the vendors. We
know a lot of the characteristics of what they're looking
for and what they cater to. And even though you
may meet the number for a group, we know that

(18:58):
certain vendors like to see groups. For example, I know
Terry's talked about one group that we had. It was
on a river cruise. It was fifty people. We had
twenty five percent of the ship.

Speaker 2 (19:09):
So you can see choosing the right vendor is equally
as important as some of the other components that we've
been talking about. The other thing when you are choosing
The right type of group experience, though, is choosing the
style in which you want to see what you're doing.
Because there's guided tours, there's semi guided tours, and there's

(19:32):
completely one hundred percent independent type vacation experiences. So if
you're thinking guided tours, which a lot of group travel
is sort of tailored to that. Because people want to
make the most of their time, they want to see
the most, they want to learn the most. That's the
ideal situation and the setup with group travel. But think

(19:53):
curated kind of immersive experiences and those that are really
handled by a t god. You've got those professional tour directors.
You've got pre planned logistics. That's important, so you know
when you're going and what you're doing. And for a
lot of people who love going on group travel, that's

(20:14):
magic to them. That makes them all of a sudden
feel so secure.

Speaker 1 (20:18):
I think it also would take some of the risk
for the organizer hating their trip because they had to
organize the entire time they were on there. The pressure's off,
like somebody else through that for.

Speaker 2 (20:31):
You, absolutely absolutely, And the other thing that you get
in this imagine this imagine that you're going on a
curated group escorted trip to Italy. Well, Chris, that's going
to be an in depth cultural experience where if you
did that on your own, you're likely not going to
be able to get so much of that. And those

(20:52):
types of trips are really ideal for international travel. And
you've got and you've got culture focused groups on that.

Speaker 1 (21:04):
This is really As we're talking about this, I keep
imagining myself with like my extended family going on a trip,
and I'm thinking, Oh, we would need your help so
badly because I'm what I enjoy. I can tell you
that my sister in law would be like, really, is

(21:25):
this what we're gonna do? And I'd be like, yeah,
deal with it, and then the trip goes downhill from there. Actually,
she's a lovely person. I'm the one who's causing the problems.
Let's take a quick break and then I'd like to
get into our next segment and continue this masterclass and
group travel here on a lifeless ordinary.

Speaker 3 (21:42):
Why do you recharge your cell phone? Maybe because, just
like you, it functions much better with a little revitalization.
The wishing Well helps people refresh and revitalize with individually designed,
customized vacation planning. We'll send you anywhere in the world,
plus offer advice on packing, navigating customs and more which
just really do come true. At the wishing Well visit

(22:02):
us at two forty three and f Avenue call us
at five four zero nine zero eight two three three three,
or on the web at the Wishingwell dot biz.

Speaker 1 (22:10):
He welcome back to a Lifeless Ordinary. This is a
travel show and podcast from your friends at the wishing Well.
Every week we dig into different topics about travel. Sometimes
it's about luxury travel. This week it happens to be
a masterclass in group travel. And as you are enjoying
the discussion this morning, I would encourage you to give

(22:33):
Terry or Harry a call at the wishing Well and
ask them questions about the topics that we discuss, and
they would be happy to give you more answers and
help you with your group travel plans. Their phone numbers
five four nine oh eight twenty three thirty three. You
can also find them on nef Avenue in Harrisonburg and
on the Wishingwell dot biz. That's their website where you

(22:54):
will find a link to all previous Lifeless Ordinary podcasts.
We've already completed three segments in our show today. First
we talked about why group travel is currently having a moment.
Then we defined what the group should be and talked
about what the right type of experience should be for
our group, which brings us to segment four, which.

Speaker 2 (23:17):
Is, Yeah, we're going to pick the right destination and
the timing. And I love Chris that you're here with
us because your input on the show is so valuable
to me, because I really believe that you ask a
lot of the same questions that many of our clients do,
so you look through a different lens when we start
talking about travel. Terry and I might be the quote

(23:40):
unquote experts here, but your questions I think are pointed
toward exactly what a lot of our audience and our
clients want to know. So here's a truth most people
don't realize when they start picking the right destination and timing,
and that is the destination doesn't make the trip successful.

(24:03):
That's kind of a misnomer. People think that, but that
is not entirely the truth. The fit between the destination
and the group does, however, so you got to ask
is it easy to get to That's something that's very important.
You know, my philosophy about luxury direct NonStop. That's where
it's at man, So direct NonStop to me, that's luxury.

(24:25):
So is it easy to get to? And for a
group you're moving a lot of people to the same destination,
it's important how you're going to get them there and
the ease in which they're going to arrive. The other thing,
does it offer flexibility in some of the activities. I mean,
you wouldn't necessarily want to take people to a destination,
you know. And what comes to my mind right now

(24:48):
is a place called Necker Island. Necker Island is beautiful,
but there's absolutely nothing there. It's designed for a class
of people who are stress out of their mind and
who need to get away. This is not something you
would probably want to put type A personalities on who
really want a lot of control over what they're doing

(25:09):
and a lot of activities and we're sitting on the
beach is just not exciting to them. They want to
do things. They want a zip line, they want a hike,
they want a bike, they want to do it all.
So you need to have flexibility on your activities. And
are there enough accommodation options, you know, I'm reminded of
the conventions that Harry and I go to with our

(25:32):
parent company, Virtuoso every year. There are more than eight
thousand travel agents that converge on Las Vegas. Can you
imagine trying to host eight thousand travel agents in three
hotels that each only have three hundred rooms a piece.
Probably not a great idea. Somebody you would say, probably

(25:53):
didn't do really good planning if that's the case. So
you have to make sure that the accommodations align with
the number of people that you're taking and that you
have the right types of rooms. There are some properties
in the Caribbean that I can tell you they're smaller.
They might be one hundred and fifty room hotel, but
only a third of those rooms are going to be

(26:16):
king bedded rooms, or only you know, so many of them.
A handful are going to be double bedded rooms. And
if you're trying to place families in one room, that's
going to be a challenge for you. The other thing
is are you going to be able to coordinate everything
for your group if they have all kinds of mobility
needs and requirements. So when you're going to Europe, that's

(26:40):
a whole different ballgame. You know, we talk to you
guys here on a lifeless ordinary many times about how
not all countries, not all Caribbean destinations, are ADA compliant,
and that's something that you need to look into, depending
on what you actually have in your group.

Speaker 1 (27:00):
Can I tell you a story about eighty a compliance Washington,
d C. You think the capital city of the United
States would be compliant with all of those type of
compliance laws. One of my dear friends is in a
wheelchair and we went up for a day just to
go around d C. And yeah, they have a way

(27:21):
that you you know, are ramped so that you can
get into this museum or that federal building. But you
got to go around the back of the building and
then you have to circle back to the front of
the building to get back into the line that you
would have started with that was two steps away. And
not only was this miserable for my friend because you know,

(27:42):
he's wheeling himself, it's not a powered wheelchair, and so
he's going to go all this extra distance, but for
those of us who weren't in wheelchairs, we were walking
that distance too. And then we decided to take the
metro and the station we needed to get to the
elevator was broken, so we had to go three stations
farther down to be able to just cross over to
come back up. And I say all of that not

(28:05):
to complain about Washington d C. Washington d C. It's
a lovely place that I enjoy visiting. But if you
want to talk about going to Europe or the Caribbean
where ADA compliance wouldn't be the same as it is
here in the States, don't think about it's crazy Anne
Ethel who's going to be miserable because she's got a walker.
You're going to be miserable with her because you're all

(28:26):
going to have to accommodate for the lack of accommodations
in your travel location.

Speaker 3 (28:32):
And when you talk about ADA, a lot of times
we talk about mobility issues. As you just did, there's
more to it. I had a group it was two
years ago where mobility wasn't an issue for some of
my travelers. I had a couple, both of whom were
legally blind, and so signage was important, and not just
signage for emergency things. But as I planned the activities

(28:56):
in this group, Chris, it was important for me to
make sure that the places we were visiting had things
either that they could listen to, or that they could
you know, run their hands over and read the burreille.

Speaker 1 (29:08):
I would have never thought about that, Like, if you're
in you know, Italy, braille isn't going to be Maybe
they would have it in English. But if you don't
speak Italian and you can't see where you're going, it's like, oh.

Speaker 3 (29:22):
That'd be a huge problem. But the good news is
if you're planning for groups, there are some excellent tools,
and we have some resources. And interestingly enough, if you
talk to the people who need those accommodations, they're aware of. Yeah,
some of the things that are out there too. One
of these two people happened to be a tester for

(29:42):
Apple Computer. It was testing you know, tools to help
the blind and so on the trip he was showing
me how he could adapt to this tour. But beforehand
he and I had a nice discussion about what he
might want to be doing and his partner, you know,
what she might want to be and I had to
think about how to make that easy for them on

(30:04):
this tour.

Speaker 1 (30:05):
I know I say this a lot, but I love
that your I don't believe Terry's been doing it forty
eight years, but your your combined years of experience allows
you to be able to think about things. That's such
a granular detail about making sure every person's having a
great experience in their trip.

Speaker 2 (30:22):
We hope, So that's our wish anyway. And in addition,
I have a special needs daughter, so people who come
to us with special needs I already have sort of
a plan in place that I know how to deal
with those things as well. The other thing that's really
important when you're choosing the right destination, as I mentioned before,

(30:44):
is timing. You know, we talked about that. We've talked
about that many times here where shoulder season is kind
of one of those magic times when you can get
the best value, best bang for your buck, so to speak.
You want to avoid peak pricing windows when possible, because
with groups that can just be a nightmare in terms
of hotel availability, air availability, that kind of thing. Moving

(31:08):
a group is not for the faint of heart if
you're traveling in peak season, So that's something to consider.
And then you've got school schedules if children are involved,
so you want to make sure that you're planning during
a time when they're going to be free to go
and not planning those trips when parents can't go because
kiddos have something to do, you know. So we're finishing

(31:30):
up the picking the right destinations and timing. We're going
to move in Chris now to step four, and that
is this is really critical. This is setting the expectations
early and this is where successful groups kind of separate
from stressful ones. I'm going to say, because from the
very beginning, you want to with your group, If you

(31:54):
are again the one who's the organizer, you're going to
want to from the very beginning, commune indicate a payment schedule.

Speaker 1 (32:01):
What is that?

Speaker 2 (32:02):
When do these people have to have money on the line?
When is the deposit? When is the final payment? Does
that coincide with any holidays? Ooh, that's a tough one,
you know. So if you've got final payments that are
coming up right at Christmas time, that could cause some
people to back out.

Speaker 1 (32:19):
As as a travel expert, are you doing the billing
for each individual member of that group or is that
the family member who's organizing? Are they hitting everybody up?
Because I can tell you that sounds like a great business.
If not that I can be the person because I
don't as a family member, I don't have to call
my cousin Jen and be like, where's the money. We're

(32:41):
all going to hate each other by the time the
vacation role's a run.

Speaker 2 (32:44):
Yeah, And the truth is, yes, we do communicate with
our clients, especially when the wishing Well has been the
one organizing the group. For example, we've got an upcoming
group to going to Hawaii. Harry's going to lead that group.
He's going to escort that group to Hawaii, and it's
been my job and his at the wishing Well to

(33:05):
communicate individually with each one of these couples that are going.
Now on the flip side of that, let's just say, Chris,
you are the one who is coordinating a group. You
bring that group to the wishing Well and you say,
I want to be the lead on this and any
communications I'd like for you to go through me. That's fine.
We respect that. And then you in turn communicate to

(33:28):
your group based on the information that we feed to you.
So for deposits requirements, final payment requirements, all of that
we tell you and then you tell your group. Many
times that works out just fine because in many cases
that can be a family. The other thing that we
like to communicate two group members are the cancelation policies,

(33:51):
what are they, what's going to happen there? And insurance.
We want to make sure that everybody has an opportunity
and understands the important and the value of insurance. And
then what's included in this trip and what is not.
Just about every single time I set down with folks
and go over their final details of their documents, I

(34:13):
always say, as a recap, let's go over what your
trip does include and what it does not, and then
the activity levels. People want to know what to expect,
you know, how much do I have to do versus
how much do I want to do? And then your
room categories. People always like options, you know, sometimes it's

(34:34):
a budget thing for people, so they would rather take
a standard room perhaps than an ocean view or a
cathedral view or a view of the Doomo in Italy.
So having the views being explained to people and the
price point differences, that's very important to folks, and just
about most importantly, not every request can be accommodated. That's

(34:58):
something we always like to te tell people up front
is that we request what we can, but not everything
can be guaranteed. For example, I will tell you, Chris,
if you went today and booked on xyz dot com
for a hotel, Okay, that's really not a site, but
I just made that up. So if you went on

(35:20):
that site and you booked a hotel, chances are you're
going to get a disclaimer at the end of that
that says room types are on request and cannot be
guaranteed they will be assigned upon check in. That's a
very important statement and one that everybody wants and needs
to be informed of when they're booking anything, especially a group,

(35:43):
because if you can, and we know this from previous experience,
everybody likes you know, let's take a cruise. Everybody likes
balcony rooms. They want to know when they book on
a cruise that they've got what they expected, what they requested.

Speaker 1 (35:58):
Now, if I'm booking just a trip for my wife
and myself, everything I request can I get? Not exactly,
not even that.

Speaker 2 (36:07):
No, I mean, you know, certain things are on request.
It's up to us to talk to you about the
bedding situation. You know, is it going to be a
room with a king or could it possibly be two queens?
The answer is yes, because those rooms are assigned upon
check in. And as you well know most of our

(36:28):
listeners know who do any traveling at all, hotels have
a hard checkout time, usually of eleven o'clock in the morning,
but there are a lot of people who push that
envelope or who have extended checkout times. Depending on their
level of priority with that hotel. They might not check
out till noontime, and they might be checking out of

(36:50):
a king bedded room or one with two queens, and
that's what you want, and that's the only one that's available,
And so if you wanted your room when you first
check in, and they might have to assign something else. Now,
many times you can say I'll take that, and if
you have one, I'm happy to change rooms that can
be accommodated as well. But the simple truth is not

(37:14):
every request can be accommodated, and that's not necessarily something
we like to have happened. But that's okay. You know,
we do the best we can with that because group
travel isn't about customization. For one, it's not. It's about
creating an experience that works for the many beautifully most

(37:36):
of the time, and with that you can pretty much
guarantee that people are going to have a good time.
So we're going to move into step five now, and
this is appointing a leader and defining their role. And Harry,
I'm going to turn this over to you because at
the wishing Well, Harry sort of occupies this leadership space.

(38:00):
I'm pretty much the one behind the scenes who does
a lot of the logistics and the coordination, and Harry
is kind of our point person and he becomes in
many cases the leader on these groups. So this is
a pretty important category, and I want him to talk
about this from firsthand knowledge.

Speaker 3 (38:18):
Yeah, having the leader is really important. It's important for
the group because as a group wants to do things,
somebody's got to receive those requests and kind of help
manage those requests and normalize them. As Terry said, not
everybody gets every single thing that they want, So the
group leader's job is to kind of be that person

(38:41):
that makes a little bit of that compromise happen when
it's necessary. I'm more important for the people that are
on the other side, the people that were visiting the
ships that we're on, the places that we're going, the
people who are providing transportation. They don't want to hear
from every voice in the group. They want to hear
from a voice in the group. And what's great about

(39:04):
having a group is that if one person comes up
and speaks to you and say, Chris, I'm speaking to
you on behalf of these thirty people, and somebody else
comes up and says, hey, Chris, I need something from
my room, You're likely going to give me the most
of your attention because if you satisfy me, you've just
satisfied to thirty people, not one person, and that's really important.

(39:29):
The group leader helps maintain consistency. One of the things
that I always do with my groups is I say,
when you get into a hotel, when you get onto
a ship, make sure that things are as we expected
them to be. If you have an issue, come let
me know. I take those issues. And again, as a
group leader, I go to the person in charge and

(39:49):
I have a liaison. I go to that person. I say, hey,
we've got two or three things that need to be
corrected here, two or three tweaks. And again my voice
is louder because I'm representing a lot of people and
because as a travel professional, they know where I'm going
to back off or where I might not back off.
So they're likely to help us. That's really important. By

(40:15):
the same token, the group leader is not the person
they're trying to manage the trip along the way. I'm
not there trying to tell people what you must do.
Terry talked about this earlier. Some people are going to
want to do different things. My job is to guide
the communication within the group and be that that normalizer

(40:35):
that makes our group function as a group. And because
we all know each other, there's that little bit of compromise.
If you know, if I want to do something at
a certain time, you want to do something at another time.
My job at the leader is to try and find
what's a good time that works for both of us.
And you will compromise if you're in with a group,
won't you.

Speaker 1 (40:55):
Well, I was just thinking, you really have to have
the right person as your leader. It's got to be
someone who's calm, Somebody who can handle the pressure of
all those details. Somebody who is easily frazzled would not
be a great group leader.

Speaker 3 (41:09):
No, stresses are not not a good characteristic for a
group leader to not be able to manage stress. Because
it is stressful, things happen, things go wrong. It may
be the weather. It may be a supplier, it may
be a person within the group. And I've sat down
with people and say, hey, you know, Chris, you're not
being reasonable. You know the other people need this. Is

(41:30):
there a way that we can satisfy you without having
you unhappy about every single thing that we do. That's
part of my job as a group leader, and to
do it tactfully, purposefully, and to have you say yeah,
I get it.

Speaker 1 (41:46):
So it seems to me that if we're talking about
a group where like the Wishing Well has put together
a group travel event, and my wife and I decide
we want to be part of that group as the
group leader, that's a different ex experience. Then if I
decide to be a group leader and I'm taking my
wife and our extended family, and because the relationship is different, yes,

(42:11):
you speaking to someone that you didn't meet until you
booked them to be part of your group travel has
got to be a different conversation than me talking to
my aunt saying hey enough, yeah, we're not here for you,
or we're here for everybody.

Speaker 2 (42:26):
Yeah.

Speaker 3 (42:26):
I cannot talk to the group and say hey, I'm
the dad here. You know, that just doesn't work. So
the group leader is really a person who is a diplomat,
a person who is someone who can negotiate and mediate,
and we do that within the group, and we do
that outside the group. However, you are leading your group

(42:48):
and you have your antalong with you. Part of my job,
part of Terry's job, is support for the group that
you brought to us at the wishing Well is say, Chris,
here's some things you might run into. Here's a little coach,
and it's our job to coach you and prepare you
for some of those and also to be the person
you call when you're like, I'm ready to throw her

(43:10):
off the bus or out of the voat or whatever.
It is. Our job is to be your sounding board
and your cushion.

Speaker 1 (43:19):
I love that we're talking about this specific topic, especially
the part about the group leader, because when I think
travel professionals, the first thing I think is that's who
I call in the book my plane or I can
get a great deal at a resort somewhere because they've
got they know people. You're so much more than that.

(43:40):
I mean, I know that because we talk every week
about what the wishing Well is, but it's almost like
you've got more of a degree in psychology than you
then really knowing the systems of how to type in
the information to get my reservation books.

Speaker 2 (43:58):
It helps, Chris, And I'll tell you, every single day,
every single minute, every single hour that we're at the
Wishing Well, we are in the process of peeling the
onions back of what our knowledge consists of and how
to use that best for our clients. So, yes, you're right,
we are not a one hit wonder at the Wishing Well.

(44:21):
We don't just do a one and done. We don't
just do package tours. You know, we do things that
are astounding, and I'm glad to hear you say that.
I mean, sometimes we think we're pretty amazing, but you know,
in the greatest humility, we know we're not. You know,
we know we're only as good sometimes as the tools

(44:42):
and the vendors that we have, So we're we're humbled
when people do think that we do a great deal.

Speaker 3 (44:49):
One quick story I want to share with you directly
talking about what we're just talking when we're going through now, Chris,
is that I had a trip one time where our
group stayed at a hotel and the hotel had a
great reputation, had a great rating. However, for us, they
didn't meet our standards. There were some shortcomings. I had

(45:10):
a traveler came in this week and was talking to
me and they said, one of the things we remember
about you, Harry, is on that trip you got us
launched on that day and our daily activities. We were
doing some touring that day, and after you dropped us off,
you jumped in a limousine that this hotel had sent
to pick you up, and you went back and went

(45:30):
through and remedied the problems that we had had, you know,
with our rooms in that hotel. And then you came
back and then you disappeared again, and I said, yeah,
I sent the limousine to come get me again because
I wanted to see that they had, in fact cleared
up all of the issues that I had pointed out
to them in the morning. Checked that out, and then

(45:51):
I came back and joined you, and you know, we
resumed our trip and everyone went home in their hotel
was in great shape. That's the kind of skis I'm
not worried about AI, you know, taking over that kind
of skill. It's problem solving skill, not knowledge skill that
AI you know can help us with in a lot
of the other work that we do.

Speaker 1 (46:13):
Our episode is entitled a master Class and Group Travel.
I'm enjoying the conversation we've talked about first five steps. Well,
first we discussed why group travel is having a moment.
But the first five steps we're defining your group, the
right type of experience, location and timing, setting the expectations early,

(46:34):
and appointing a leader and defining their role. And there's
still more to talk about in this master Class and
Group Travel, which we'll talk about next here on a
Lifeless Ordinary.

Speaker 3 (46:43):
Why do you recharge your cell phone? Maybe because, just
like you, it functions much better with a little revitalization.
The wishing Well helps people refresh and revitalize with individually designed,
customized vacation planning. We'll send you anywhere in the world,
plus offer advice on packing, navigating in customs, and more.
Wishes really do come true.

Speaker 1 (47:03):
At the wishing Well.

Speaker 3 (47:04):
Visit us at two forty three and a half Avenue,
call us at five four zero nine zero eight two
three three three, or on the web at the Wishingwell
dot biz.

Speaker 1 (47:12):
And welcome back to a Life Less Ordinary, The travel
Showing podcasts from your friends at the Wishing Well they're
on ne f Avenue in Harrisonburg. They're online at the
wishing Well dot biz. That's the wishing Well dot biz.
When you land on their website, there's tons of information
about all kinds of travel experiences. But in the upper
right hand corner a little gift for you. There's a

(47:34):
link to a Life Less Ordinary and you can go
back and listen to six years worth of podcasts as
we discuss different travel topics. You can also give them
a call at five four h nine oh eight twenty
three thirty three. The show this week is entitled a
Masterclass in Group Travel and we're up to step six.

Speaker 2 (47:52):
We are and we are going to look at understanding
the financial structure of a group trip because that's very
important and this is where really Chris experience matters the most,
I would say, because group travel often includes deposits and
those are tied to the space that you're going to
hold for your group. So that's very important. You have

(48:15):
to have you have to be somebody who's very responsible
to do that, first of all, and then you've got
what are called attrition policies, and let me explain that
to you. There are certain times during from the booking
date until your travel date that a tour operator or
a cruise line or an airline will give you as

(48:37):
what I call magic dates. Those are magic dates that
you need to put on your calendar and you need
to remember them because once you get to like the
first date that they give you, you have until that
date to reduce your number in party. If you have
failed to reach the number that you had hoped to
or that you had booked, or you're going to pay

(48:59):
for those seats anyway, that's when negotiations with vendors become
really important. You need to know what you can ask
for and what you can't, because that's when the experience
of a trained travel professional really becomes your best friend
in this type of the booking process. And then you've

(49:22):
got final payment deadlines. You're going to want to make
sure that you don't miss those because you know if
you do, space goes away. And the worst thing that
could happen is let's just say you started this group
a year ago and you've done everything correctly. You did
your deposits, you adhere to the attrition dates. Something came

(49:43):
up you completely forgot your final payment date. That's a
very important date for vendors, tour lines, airlines, and if
you miss that date, they assume you're not going to
move forward and they will cancel the space. That's a
devastating thing to have happened. So those are some things
that you do need to understand about the financial structure.

Speaker 1 (50:06):
If that happens. If I missed that final payment and
they cancel, I guess you're canceling your trip in essence, if.

Speaker 2 (50:12):
The trip does get canceled, yes.

Speaker 1 (50:14):
But everything I've paid up to that point, does that
disappear as well?

Speaker 2 (50:18):
Like kens, if you have travel insurance on the booking,
sometimes that's protected sometimes, Chris, and this is where you
have to read the terms and conditions. Sometimes deposits and
money's paid on a guaranteed group are non refundable.

Speaker 1 (50:34):
So all right, when the wishing well decides you're going
to do the Hawaii trip you said is coming up,
you're taking that financial risk. We are, You're paying those
payments along the ways, And so as a person who's
joining that group, I've got a little less concern and
worry about those specific dates. Right, But if I'm the

(50:56):
organizer of my own group travel, should I make sure
I have all my money up front before I even
start like booking things, so that I guarantee that I'm
not going to be out that money, or am I
trusting my family that they're going to hit their payments
along the way so that I don't miss any of
those deadlines.

Speaker 2 (51:14):
Yeah, well we if you are a group pod piper
and you're working with a travel professional, your travel professional
is going to coach you all the way through and
give you all the paperwork on dates that are going
to be that you need to be considerate of and
when money has to be in on those. So that's
something that you want to work very closely with your

(51:36):
provider with. But here's a key message for everybody here.
Pricing is time sensitive. You need to be aware of that.
Space is usually limited on groups that figures into the
financial structure because you know it's all about yield, so
you know it's all about supply and demand, So you

(51:58):
have to be aware of that, and hesitation can really
cost your group significantly. I've had it happen before where
people have reached out to me they've wanted to plan
a group, They get quotes, they say to me, I'll
get back to you. They wait a month, they get
back to me, space is gone, so that can happen.
So those are things you need to understand. And I
want to move pretty quickly through the next steps because

(52:20):
I really don't want to leave people hanging at the
end of our masterclass here. But step seven, Chris is
you want to build in some flexibility. So even in
a structured group, flexibility is oh good, Lord, is so important.
You want to allow some free time for your travelers.
Give them some options. You know, Harry was talking earlier
about options. You want to give people optional excursions, optional

(52:43):
things to do, independent dining as well as group dining opportunities.
So sometimes people who are traveling together they want to
eat together. Other times not so much, because not everybody
travels at the same pace or the same likes and interests,
and the best group experience they balance together time versus

(53:04):
personal time. So that's really really important. Our step number
eight here, this one I think is huge, almost should
have been at the first Communication is everything clear and
consistent communication with your group really prevents nearly every issue
that you could possibly have. Successful groups are going to

(53:26):
use email updates and scheduled meetings and in person or
we even do those via zoom or virtual final document reviews.
And one of your strongest different differentiators is pre travel gatherings.
We do that as a rule. That's kind of our
religion at the wishing will we do that with everybody.

(53:47):
We build in excitement, we answer questions, we create connected
experiences before their departure. And then finally, Chris the ten
biggest mistakes to avoid, and let's be honest, this is
where people kind of lean in trying to please everybody.
Can't do it. It's not possible. Waiting too long to commit.

(54:07):
We talked about that. Not understanding the terms and conditions
of what you're signing up for. You better know, over
complicating your itinerary. You've got to simplify things, you know,
there's a reason why people say keep it simple. Poor communication,
and the biggest one of all is not working with
a professional. Because group travel is not just booking travel.

(54:31):
It's managing people, expectations, logistics, and timing all at once.

Speaker 3 (54:39):
So hopefully today we've sent a message that does group
travel is not just about getting someone to the same
place at the same time. It's about orchestrating that whole process.
It's about coming home and feeling different. You've got the
right people, you have the right experiences, and you've put
that all together so that people come home home feeling different.

(55:01):
They're closer, they're more connected, they got stories that belong
to the group. When it's done right, this is a
fantastic trip and more, it's a shared chapter in your lives,
whether it's friends or families you're going to talk about
for a year to come. So if you're thinking about
bringing a group of people together, maybe it's the magic

(55:21):
moment to start picking action on that. Let us know,
and we're always here to help. And now we hope
you walk away a little bit smarter about the process.

Speaker 1 (55:32):
And now we all get diplomas from this masterclass.

Speaker 2 (55:34):
Absolutely, And if you want more information on how to
build a group or any other travel interests that you have,
you can find us at the Wishing Well. We're at
two forty three f Avenue in Harrisonburg, Virginia. You can
look us up on the web where at the Wishingwell,
dot biz or call us. We'd love to talk to
you at five four zho nineh eight two three three three.

Speaker 1 (55:54):
This has been a life less ordinary. The travel show
from your Friends at the Wishing Well at two forty
three No Avenue in Harrisonburg. If you have any questions
on topics discussed today, please reach out to the wishing
Well online at the Wishingwell dot biz or five four
oh nine oh eight twenty three thirty three. Past episodes
are available on the iHeartRadio app. And we'll see again
next Saturday morning at ten for a life less Ordinary

(56:17):
from the wishing Well
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Bobby Bones Show

The Bobby Bones Show

Listen to 'The Bobby Bones Show' by downloading the daily full replay.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices