November 19, 2025 • 17 mins
Planning a trip with multiple generations of your family? Before you book, listen to this essential episode! Travel advisors Ryan and Julie share hard-won wisdom about the most common mistakes families make when planning multi-gen vacations—and how to avoid them.
From the planning phase through your actual trip, they cover everything: why you need to nail down dates BEFORE contacting your travel advisor, the importance of having a "team leader" for your group, and why trying to do everything together is a recipe for stress (spoiler: those Disney families of 20 walking in a line aren't having as much fun as you think).
Discover why cruises and all-inclusives work so well for multi-gen groups, how to handle different budgets within the same family, and the critical conversation about who's paying for what. Julie shares real stories from her own family trips and client experiences, while Ryan offers practical tips about room configurations, meeting points, and making sure everyone's expectations are aligned.
The hosts emphasize that while planning some group activities is important, the magic often happens in the unplanned moments—cousins running to each other in the Magic Kingdom, spontaneous trivia sessions on the cruise ship, or simply sharing a meal together. They also tackle the delicate balance of ensuring the person treating the family doesn't have their preferences overlooked.
Whether you're planning a cruise, Disney vacation, or all-inclusive getaway with grandparents, siblings, and kids in tow, this episode will help you create a memorable trip that brings your family closer together—without the drama.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
j_1_10-31-2025_145008 (00:10):
Hello and welcome to All Things Travel.
One of our areas of expertise ismulti-generational travel.
type of travel has become reallypopular over the last few years
as families are truly busierthan ever, and a multi-gen trip
is a great way for everyone toget away together and have some
(00:30):
quality time without.
Having to clean the house and dothe dishes and all those kinds
of things.
So today we're gonna tell youabout what not to do when you're
planning your multi-gen trip andthings to think about for during
your trip.
ryan_2_10-31-2025_145008 (00:47):
Listen in with travel advisors and
destination experts.
Ryan and Julie.
I'm your travel professorteaching you everything you need
to know to have a magicalvacation, and she's a Disney
loving Maryland mom of three anda specialist in family travel.
Whether we're discussingincredible destinations, top
vacation tips, or sharingpersonal stories, it's always
(01:09):
all things travel.
Julie, this is really yourwheelhouse, isn't it?
I've planned many multi-gentrips, but this is really your
bread and butter.
j_1_10-31-2025_145008 (01:22):
It's, and I kind of started with that
because I was personally takinga lot of multi-generational
trips with, my family in-lawsextended family, nieces,
nephews, things like that.
So obviously I just learned alot from that, that I can share
with my clients and I feel likeit lends a lot to my client
base, to my niche, which is
ryan_2_10-31-2025_145008 (01:42):
Yeah.
Yeah.
j_1_10-31-2025_145008 (01:43):
with young kids.
There's always thosegrandparents that also want to
go with them, or maybe abrother, sister, cousins.
So there's a lot to think aboutwith these trips we thought it
would be a great idea to kind ofrun down things you need to know
when you're thinking about thistype of trip.
ryan_2_10-31-2025_145008 (01:57):
I love it.
Well, before we get into thelist, I wanna remind folks if
they did not listen to lastweek's episode.
We talked all about Alaska shoreexcursions.
j_1_10-31-2025_145008 (02:08):
so I wanna start with mistakes that
you could make.
While you're planning your trip,and I think the most there,
there's two like very importantones here, and they're
ironically at the top and thebottom of my list.
ryan_2_10-31-2025_145008 (02:20):
Okay.
j_1_10-31-2025_145008 (02:20):
everyone should sit down and plan your
dates before contacting yourtravel advisor.
if you're unsure, which seasonis best for your family or for
your.
Donation, at least have a fewdate ranges in mind.
otherwise it feels like a littlebit of a waste of time to be
going around in circles.
And then your sister's familysays, oh, we can't do that week.
(02:44):
when you come to us, we want tomake sure everyone is on the
page about when you're going.
ryan_2_10-31-2025_145008 (02:49):
So the mistake is not knowing when
people are available and nothaving that ironed out.
Okay.
I gotcha.
j_1_10-31-2025_145008 (02:55):
because you could say, oh, we really
wanna go at this time of year,and then you forget so and so
has a baseball tournament, orthis one is in the school play.
Or, you know, mom and dad can'tgo during this time.
just have your dates ready togo.
ryan_2_10-31-2025_145008 (03:09):
Got it.
j_1_10-31-2025_145008 (03:09):
like when multi-generational groups have a
group leader.
someone that I can contacteasily, but I also want everyone
to be available on a phone call,or on our zoom meeting,
ryan_2_10-31-2025_145008 (03:25):
Yep.
j_1_10-31-2025_145008 (03:25):
it is, because that way I know that
everyone is on the same page.
It's challenging sometimes toplan a troop when sometimes you
have that part of your familythat's like, I don't care.
Just tell me what to do andwhere to go.
And then you start planning andthen they realize
ryan_2_10-31-2025_145008 (03:40):
And at, at, at the 11th hour, they
swoop in and you're like, I havenot talked to this person at
all.
And now they're changing thingsup.
Yep.
I've been there, done that.
even with a friends group, youknow, I'm thinking of a recent
river cruise.
with four friends.
there was one person who I hadworked with before, and that
kind of turned into the teamleader because I had a rapport
(04:02):
with her more than the otherwomen.
another thing you wanna makesure you do in the planning
phase is make sure thateverybody is in agreement with
at least the destination, themain activities that everybody's
going to do, and also a generalprice range.
Now, I will say as a traveladvisor, we can offer
differences, so some people canstay in a garden view room
(04:26):
versus others who want to stayin an ocean view room.
Or we can have some people go ona more extended activity and
other people don't.
So we can within the group,change those things.
But you need to have some ofthose key larger group things
nailed down.
j_1_10-31-2025_145008 (04:43):
And what this reminds me of is a lot of
times I'll have a multi-gengroup come to me and say, we all
wanna go on this cruise nextsummer.
And so we start researchingcruises.
And then they come back, okay,well nevermind.
My sister is very much against acruise.
ryan_2_10-31-2025_145008 (05:01):
Right,
j_1_10-31-2025_145008 (05:02):
well where are we going then?
I have that happen More oftenthan I'd like.
Try to choose a destination thatoffers something for everyone
and something that they can doon their own time.
cruises and all inclusivesreally play into this because at
an all inclusive, if so and sowants to go sit on the beach all
day, great.
(05:22):
The other family can go to thepool all day.
You don't have to be side byside all day.
similar to a cruise, you couldbe doing activities on board,
you could choose differentexcursions at a port.
Disney can be a little bittricky with this, but I have
created multiple touring plansfor the same family or written
into one touring plan.
(05:43):
little kids can do this ridewhile
ryan_2_10-31-2025_145008 (05:45):
Right.
j_1_10-31-2025_145008 (05:46):
go do this.
Something like that is reallydoable.
or maybe the grandparents wannatake a break that day.
it's doable.
It just takes a little bit morethinking, We mentioned this
briefly, but choose adestination that also offers
different price points.
Ryan mentioned choosing thatgarden view room versus an ocean
view, or different excursions.
(06:07):
This is why I love a cruise formulti-gen, because you could be
in an inside cabin and oceanview, a balcony, concierge.
There's so many differentoptions to truly fit everyone's
needs.
can do that similarly with allinclusive, and
ryan_2_10-31-2025_145008 (06:23):
Yeah.
j_1_10-31-2025_145008 (06:24):
you can do that similar with Disney, but
a lot of times what ends uphappening with Disney is you may
end up at different resorts.
so I tend to say let's pick amoderate level price range that
everyone's in agreement with forDisney as opposed to forcing
everyone to go higher or lower.
and along with that, you may notto book that three bedroom.
(06:46):
Villa or apartment that everyonecan fit into.
You might want to have ownspaces
ryan_2_10-31-2025_145008 (06:53):
some space.
Yeah.
A lot of people come to us andthey say, we want to have a
place where everybody can betogether, and that's great and
there's certainly options forthat, but also having distinct
places for each family Doesn'treally hurt, especially if it's
a longer trip.
think of number of bathrooms,quieter spots for people that
(07:14):
want to take naps, whether it bekids or adults.
being on top of each other on atrip like this is not
necessarily always the most fun.
maybe grandma and grandpa have alarger room and that becomes the
clubhouse, And then at the endof the day, everybody leaves and
they have their own space.
j_1_10-31-2025_145008 (07:29):
I've done trips like that before where
grandma and grandpa have like avilla and everyone can
congregate in that common space.
Or I've also done it where,multiple families are in a club
level location.
the club level lounge kind ofbecomes their communal
ryan_2_10-31-2025_145008 (07:44):
Yeah.
Yeah.
j_1_10-31-2025_145008 (07:45):
not private obviously, but still a
great place for gathering.
ryan_2_10-31-2025_145008 (07:49):
Julie, along with having that team
leader, one of the things thatis really important and your
team leader can help you with isgetting everybody's contact
information.
What's the information that youare going to need to make the
bookings to change things aroundif needed?
if the travel advisor's helpingyou with flights, do you need to
(08:10):
know the known traveler numbersor their frequent fire numbers?
You know, all this kind ofstuff.
even if you're not working witha travel advisor.
It's important for a person tohave all of that because they
may be calling the hotel on yourfamily's behalf.
j_1_10-31-2025_145008 (08:25):
Yes.
And it's hard to be like, well,it's so-and-so's sister, but I
don't actually know their email
ryan_2_10-31-2025_145008 (08:31):
Yeah.
j_1_10-31-2025_145008 (08:31):
that.
ryan_2_10-31-2025_145008 (08:32):
Yep, absolutely.
j_1_10-31-2025_145008 (08:34):
the next one is, Really important.
Decide who is paying for what inadvance.
Sometimes this looks likegrandma and grandpa are paying
for everything, but when theysay everything, do they also
mean meals?
Do they also mean flights?
Do they also mean transportationor they truly mean or the cruise
(08:56):
itself?
you could also divvy this up asfar as.
Things like, so-and-so is payingfor transfers and this person's
paying for an excursion.
we need to know, and you need toknow in advance who is paying
for what.
So there's no confusion on that.
I also wanna say to plan toarrive together, and this is
(09:16):
more for ease of transportation.
You know, it doesn't make senseif you're all arriving on the
same day to have flights comingin at very different times.
It's just easier to just do onetransportation.
And the very last one for thisis to make sure you have
expectations set in advance.
This can just avoid a lot ofarguments.
(09:38):
that this family has must dosand the other family has must
dos, and it's okay if those aredifferent.
Must dos.
ryan_2_10-31-2025_145008 (09:45):
and it really is hard for us sometimes
when we see, one person isreally treating their family to
a trip
j_1_10-31-2025_145008 (09:52):
Mm-hmm.
ryan_2_10-31-2025_145008 (09:53):
their expectations are the last ones
to be considered.
it is sometimes balancingpriorities within a group and,
and not often, but, you know,there's been some interesting
conversations when it comes toplanning these types of trips.
j_1_10-31-2025_145008 (10:07):
Always.
ryan_2_10-31-2025_145008 (10:08):
Julie has a lot more suggestions for
during your travel, but firstshe's gonna talk about a cruise
when it comes to where in theworld is Wonder and Beyond
Travel.
j_1_10-31-2025_145008 (10:20):
Yeah.
And this one is exciting becauseit's a personal cruise and
ryan_2_10-31-2025_145008 (10:24):
Nice.
j_1_10-31-2025_145008 (10:25):
soon.
I'm pretty sure by the time thisepisode comes out, I will be
back and I can't wait to talkabout it later.
this is exciting because it's aseminar at sea, so that means
that we were invited to go tosome training with Royal
Caribbean, and that trainingjust happens to be on a cruise
ship in the Caribbean.
I will be doing a four nightcruise on the Wonder of the
(10:45):
Seas, which is in oas.
This class ship similar toUtopia of the Seas that we were
just on, but a little bitdifferent.
my husband is coming with me.
We have a Ocean View balconyroom, which was assigned to us.
I was very pleasantly surprised.
we have a couple days oftraining, we go to Nassau, but I
believe the day we're at Nassau,we have a, a morning of meetings
(11:08):
and trainings and, and meetingwith Royal Caribbean.
so I'm excited for that.
Our day at sea, we're inmeetings a lot of the day, but
we also get to try some of thespecialty restaurants throughout
the day, so
ryan_2_10-31-2025_1450 (11:18):
Awesome.
j_1_10-31-2025_145008 (11:19):
for that.
and then of course we havePerfect Day Coco K, we are
getting a tour of the island.
And then I have booked us forHideaway Beach.
I wasn't gonna do that'cause Ijust wasn't sure if I wanted to
spend the extra and you know,would we have time?
But then I kind of thought, whenelse are we going to be going on
(11:41):
a careers without children that
ryan_2_10-31-2025_145008 (11:42):
Yeah.
j_1_10-31-2025_145008 (11:42):
to Hideaway Beach?
ryan_2_10-31-2025_145008 (11:44):
even if you just go for a couple
hours after you're done withyour stuff, I still think it's
worth the price.
j_1_10-31-2025_145008 (11:49):
yeah, absolutely.
Steven's not going on the tour,so he can go hang out at
Hideaway Beach
ryan_2_10-31-2025_145008 (11:53):
Yeah.
j_1_10-31-2025_145008 (11:54):
I will be working a lot on that trip.
So Steven is also planning onworking a lot on that trip, and
that's how we're, justifyingthis one.
ryan_2_10-31-2025_145008 (12:01):
Okay.
we will be anxiously awaiting tohear how much work you and
Steven actually get done on youradults only crews
j_1_10-31-2025_145008 (12:09):
I'm excited.
ryan_2_10-31-2025_145008 (12:10):
we love learning about where our
clients are traveling, even whenwe're the clients.
That's part of the fun, and wealso love to highlight them on
the podcast.
So who knows?
Maybe if you work with WonderBeyond Travel, your trip will be
featured next.
All right, Julie, we are doingthe trip.
We've done the planning.
(12:32):
The number one thing is, likeyou said, set the expectations.
and I say this every time I workwith a multi-generational trip,
do not try to do everythingtogether.
If you're the Disney family of20 walking down the sidewalk, or
if you think everybody needs topick out their pool chair by 7
(12:54):
45 in the morning, you're gonnabe.
Really stressed out anddisappointed by the end of the
trip.
j_1_10-31-2025_145008 (13:01):
Yeah, that sounds exhausting.
And, you know, it sounds sotempting to, have one big plan
and we're all gonna do this andit just doesn't end up working
out.
What I've found in largergroups, especially at a place
like Disney, is you spend halfthe time waiting for people to
go to the bathroom.
As silly as that sounds
ryan_2_10-31-2025_145008 (13:22):
Oh, it doesn't sound silly at all.
Yeah.
j_1_10-31-2025_145008 (13:24):
and it's like, oh, so and so has to go.
We're gonna stop and so and so'sgonna go.
You don't have to go,
ryan_2_10-31-2025_145008 (13:28):
Yeah.
j_1_10-31-2025_145008 (13:29):
now we're gonna walk.
And then it's like, oh, now Ihave to go, or now the baby
needs to go, So just setting theexpectations that it's okay that
you're gonna do this and I'mgonna do this and we'll meet up
later.
ryan_2_10-31-2025_145 (13:39):
sometimes it's people doing stuff
separately during the day andthen meeting up for dinner.
Sometimes it's setting anevening where, the young adults
can go out and grandma andgrandpa watch the kids.
or maybe it's a time wheregrandma and grandpa get to go
out and have a date.
one of the first times I took myparents to Disney, my dad
actually found out throughsocial media.
(13:59):
That one of his high schoolfriends was staying across the
lake at another resort and hewent over and talked to him,
this family goes to Disney allthe time.
What the grandparents do is theyspend one day with each family.
So Wednesday they spend the daywith your family, and then they
spend the day with the nextfamily, and then they have a day
off.
they're rotating around.
(14:20):
They're not feeling like theyhave to be with everybody all
the time.
I kind of like that idea.
j_1_10-31-2025_145008 (14:24):
That's so interesting.
I haven't thought about doing itthat way.
I'll also mention, if you aretraveling with multiple rooms,
we can put a request in forthose rooms to be near each
other or connecting, but it isnot guaranteed.
which could be a pro or a condepending on your family.
ryan_2_10-31-2025_1 (14:41):
Absolutely.
one of the things to consider ismaybe there's meeting points,
throughout the resort.
So maybe, you know, hey, we knowthat we always meet for dinner
in the lobby, or we always knowwe meet at the pool, in this
spot.
this is the.
Exit to the, to the resort thatwe always leave from that can
really help folks.
obviously, this has changed alot with apps for the resort
(15:05):
that maybe has messaging thesame with cruises, being able to
message with the wifi at theresort or on the cruise so
people are in much more contact.
planning some of those thingsahead of time, really helps out.
I will say with all of this Asmuch as we're saying, don't try
to be together all the time.
Do plan at least a couple timeswhere everybody's together.
(15:29):
This is the time to get yourpictures.
This is the time to have a mealand say thank you to the person
that maybe has paid for thetrip.
have a couple times where youare connecting as a larger group
and take those pictures and havethat fun.
j_1_10-31-2025_145008 (15:44):
so the last big thing I don't want you
to make the mistake of is don'tmiss the little moments.
It's really fun to plan the bigmoments, to plan the big
excursions, to plan a fancy mealor to plan the big character
meal, or that we're all gonna goon this ride together.
(16:05):
But a lot of times those littlemoments are.
cousins running up to each otherwhen they first see each other
in the Magic Kingdom.
going off and doing the waterslides together at your resort,
going to a trivia session or asilent disco on your cruise
ship.
Things like that, that happenmuch more spontaneously that you
(16:26):
can't really plan.
I struggle with this, travelingwith my family and I know many
families do.
feel like you're on a scheduleto get and do the things that
you've planned in advance, andyou don't wanna miss anything.
But please make sure you slowdown, especially with a larger
group, and enjoy those littlemoments, seeing all the little
kids watching the fireworkstogether.
(16:47):
all the adults being together inone space, sharing a meal,
things that don't happen in youreveryday life.
ryan_2_10-31-2025_145008 (16:55):
I really love that.
I think that's the perfect,cherry on the top with our
discussion today when it comesto multi-gen travel.
And the last bit of advice thatI would have is if you haven't
done it and you like yourfamily, try it.
It's a lot of fun.
But notice I said if you likeyour family, the world is full
(17:16):
of wonder Your next adventure iswaiting at Wonder and Beyond
Travel.
We work with you to create a oneof a kind journey, taking the
stress off your plate so you canfocus on the joy of exploring
and the memories that will staywith you forever.
If you're ready to startplanning or you just want to
dream a little bigger, head onover to Wonder and beyond
(17:36):
travel.com, and we would love tohelp you get started.
We look forward to talking toyou next week on all Things
Travel, when we discuss onecountry, three budgets in Japan.
Hello and welcome to All Things Travel.
One of our areas of expertise ismulti-generational travel.
type of travel has become reallypopular over the last few years
as families are truly busierthan ever, and a multi-gen trip
is a great way for everyone toget away together and have some
(00:30):
quality time without.
Having to clean the house and dothe dishes and all those kinds
of things.
So today we're gonna tell youabout what not to do when you're
planning your multi-gen trip andthings to think about for during
your trip.
ryan_2_10-31-2025_145008 (00:47):
Listen in with travel advisors and
destination experts.
Ryan and Julie.
I'm your travel professorteaching you everything you need
to know to have a magicalvacation, and she's a Disney
loving Maryland mom of three anda specialist in family travel.
Whether we're discussingincredible destinations, top
vacation tips, or sharingpersonal stories, it's always
(01:09):
all things travel.
Julie, this is really yourwheelhouse, isn't it?
I've planned many multi-gentrips, but this is really your
bread and butter.
j_1_10-31-2025_145008 (01:22):
It's, and I kind of started with that
because I was personally takinga lot of multi-generational
trips with, my family in-lawsextended family, nieces,
nephews, things like that.
So obviously I just learned alot from that, that I can share
with my clients and I feel likeit lends a lot to my client
base, to my niche, which is
ryan_2_10-31-2025_145008 (01:42):
Yeah.
Yeah.
j_1_10-31-2025_145008 (01:43):
with young kids.
There's always thosegrandparents that also want to
go with them, or maybe abrother, sister, cousins.
So there's a lot to think aboutwith these trips we thought it
would be a great idea to kind ofrun down things you need to know
when you're thinking about thistype of trip.
ryan_2_10-31-2025_145008 (01:57):
I love it.
Well, before we get into thelist, I wanna remind folks if
they did not listen to lastweek's episode.
We talked all about Alaska shoreexcursions.
j_1_10-31-2025_145008 (02:08):
so I wanna start with mistakes that
you could make.
While you're planning your trip,and I think the most there,
there's two like very importantones here, and they're
ironically at the top and thebottom of my list.
ryan_2_10-31-2025_145008 (02:20):
Okay.
j_1_10-31-2025_145008 (02:20):
everyone should sit down and plan your
dates before contacting yourtravel advisor.
if you're unsure, which seasonis best for your family or for
your.
Donation, at least have a fewdate ranges in mind.
otherwise it feels like a littlebit of a waste of time to be
going around in circles.
And then your sister's familysays, oh, we can't do that week.
(02:44):
when you come to us, we want tomake sure everyone is on the
page about when you're going.
ryan_2_10-31-2025_145008 (02:49):
So the mistake is not knowing when
people are available and nothaving that ironed out.
Okay.
I gotcha.
j_1_10-31-2025_145008 (02:55):
because you could say, oh, we really
wanna go at this time of year,and then you forget so and so
has a baseball tournament, orthis one is in the school play.
Or, you know, mom and dad can'tgo during this time.
just have your dates ready togo.
ryan_2_10-31-2025_145008 (03:09):
Got it.
j_1_10-31-2025_145008 (03:09):
like when multi-generational groups have a
group leader.
someone that I can contacteasily, but I also want everyone
to be available on a phone call,or on our zoom meeting,
ryan_2_10-31-2025_145008 (03:25):
Yep.
j_1_10-31-2025_145008 (03:25):
it is, because that way I know that
everyone is on the same page.
It's challenging sometimes toplan a troop when sometimes you
have that part of your familythat's like, I don't care.
Just tell me what to do andwhere to go.
And then you start planning andthen they realize
ryan_2_10-31-2025_145008 (03:40):
And at, at, at the 11th hour, they
swoop in and you're like, I havenot talked to this person at
all.
And now they're changing thingsup.
Yep.
I've been there, done that.
even with a friends group, youknow, I'm thinking of a recent
river cruise.
with four friends.
there was one person who I hadworked with before, and that
kind of turned into the teamleader because I had a rapport
(04:02):
with her more than the otherwomen.
another thing you wanna makesure you do in the planning
phase is make sure thateverybody is in agreement with
at least the destination, themain activities that everybody's
going to do, and also a generalprice range.
Now, I will say as a traveladvisor, we can offer
differences, so some people canstay in a garden view room
(04:26):
versus others who want to stayin an ocean view room.
Or we can have some people go ona more extended activity and
other people don't.
So we can within the group,change those things.
But you need to have some ofthose key larger group things
nailed down.
j_1_10-31-2025_145008 (04:43):
And what this reminds me of is a lot of
times I'll have a multi-gengroup come to me and say, we all
wanna go on this cruise nextsummer.
And so we start researchingcruises.
And then they come back, okay,well nevermind.
My sister is very much against acruise.
ryan_2_10-31-2025_145008 (05:01):
Right,
j_1_10-31-2025_145008 (05:02):
well where are we going then?
I have that happen More oftenthan I'd like.
Try to choose a destination thatoffers something for everyone
and something that they can doon their own time.
cruises and all inclusivesreally play into this because at
an all inclusive, if so and sowants to go sit on the beach all
day, great.
(05:22):
The other family can go to thepool all day.
You don't have to be side byside all day.
similar to a cruise, you couldbe doing activities on board,
you could choose differentexcursions at a port.
Disney can be a little bittricky with this, but I have
created multiple touring plansfor the same family or written
into one touring plan.
(05:43):
little kids can do this ridewhile
ryan_2_10-31-2025_145008 (05:45):
Right.
j_1_10-31-2025_145008 (05:46):
go do this.
Something like that is reallydoable.
or maybe the grandparents wannatake a break that day.
it's doable.
It just takes a little bit morethinking, We mentioned this
briefly, but choose adestination that also offers
different price points.
Ryan mentioned choosing thatgarden view room versus an ocean
view, or different excursions.
(06:07):
This is why I love a cruise formulti-gen, because you could be
in an inside cabin and oceanview, a balcony, concierge.
There's so many differentoptions to truly fit everyone's
needs.
can do that similarly with allinclusive, and
ryan_2_10-31-2025_145008 (06:23):
Yeah.
j_1_10-31-2025_145008 (06:24):
you can do that similar with Disney, but
a lot of times what ends uphappening with Disney is you may
end up at different resorts.
so I tend to say let's pick amoderate level price range that
everyone's in agreement with forDisney as opposed to forcing
everyone to go higher or lower.
and along with that, you may notto book that three bedroom.
(06:46):
Villa or apartment that everyonecan fit into.
You might want to have ownspaces
ryan_2_10-31-2025_145008 (06:53):
some space.
Yeah.
A lot of people come to us andthey say, we want to have a
place where everybody can betogether, and that's great and
there's certainly options forthat, but also having distinct
places for each family Doesn'treally hurt, especially if it's
a longer trip.
think of number of bathrooms,quieter spots for people that
(07:14):
want to take naps, whether it bekids or adults.
being on top of each other on atrip like this is not
necessarily always the most fun.
maybe grandma and grandpa have alarger room and that becomes the
clubhouse, And then at the endof the day, everybody leaves and
they have their own space.
j_1_10-31-2025_145008 (07:29):
I've done trips like that before where
grandma and grandpa have like avilla and everyone can
congregate in that common space.
Or I've also done it where,multiple families are in a club
level location.
the club level lounge kind ofbecomes their communal
ryan_2_10-31-2025_145008 (07:44):
Yeah.
Yeah.
j_1_10-31-2025_145008 (07:45):
not private obviously, but still a
great place for gathering.
ryan_2_10-31-2025_145008 (07:49):
Julie, along with having that team
leader, one of the things thatis really important and your
team leader can help you with isgetting everybody's contact
information.
What's the information that youare going to need to make the
bookings to change things aroundif needed?
if the travel advisor's helpingyou with flights, do you need to
(08:10):
know the known traveler numbersor their frequent fire numbers?
You know, all this kind ofstuff.
even if you're not working witha travel advisor.
It's important for a person tohave all of that because they
may be calling the hotel on yourfamily's behalf.
j_1_10-31-2025_145008 (08:25):
Yes.
And it's hard to be like, well,it's so-and-so's sister, but I
don't actually know their email
ryan_2_10-31-2025_145008 (08:31):
Yeah.
j_1_10-31-2025_145008 (08:31):
that.
ryan_2_10-31-2025_145008 (08:32):
Yep, absolutely.
j_1_10-31-2025_145008 (08:34):
the next one is, Really important.
Decide who is paying for what inadvance.
Sometimes this looks likegrandma and grandpa are paying
for everything, but when theysay everything, do they also
mean meals?
Do they also mean flights?
Do they also mean transportationor they truly mean or the cruise
(08:56):
itself?
you could also divvy this up asfar as.
Things like, so-and-so is payingfor transfers and this person's
paying for an excursion.
we need to know, and you need toknow in advance who is paying
for what.
So there's no confusion on that.
I also wanna say to plan toarrive together, and this is
(09:16):
more for ease of transportation.
You know, it doesn't make senseif you're all arriving on the
same day to have flights comingin at very different times.
It's just easier to just do onetransportation.
And the very last one for thisis to make sure you have
expectations set in advance.
This can just avoid a lot ofarguments.
(09:38):
that this family has must dosand the other family has must
dos, and it's okay if those aredifferent.
Must dos.
ryan_2_10-31-2025_145008 (09:45):
and it really is hard for us sometimes
when we see, one person isreally treating their family to
a trip
j_1_10-31-2025_145008 (09:52):
Mm-hmm.
ryan_2_10-31-2025_145008 (09:53):
their expectations are the last ones
to be considered.
it is sometimes balancingpriorities within a group and,
and not often, but, you know,there's been some interesting
conversations when it comes toplanning these types of trips.
j_1_10-31-2025_145008 (10:07):
Always.
ryan_2_10-31-2025_145008 (10:08):
Julie has a lot more suggestions for
during your travel, but firstshe's gonna talk about a cruise
when it comes to where in theworld is Wonder and Beyond
Travel.
j_1_10-31-2025_145008 (10:20):
Yeah.
And this one is exciting becauseit's a personal cruise and
ryan_2_10-31-2025_145008 (10:24):
Nice.
j_1_10-31-2025_145008 (10:25):
soon.
I'm pretty sure by the time thisepisode comes out, I will be
back and I can't wait to talkabout it later.
this is exciting because it's aseminar at sea, so that means
that we were invited to go tosome training with Royal
Caribbean, and that trainingjust happens to be on a cruise
ship in the Caribbean.
I will be doing a four nightcruise on the Wonder of the
(10:45):
Seas, which is in oas.
This class ship similar toUtopia of the Seas that we were
just on, but a little bitdifferent.
my husband is coming with me.
We have a Ocean View balconyroom, which was assigned to us.
I was very pleasantly surprised.
we have a couple days oftraining, we go to Nassau, but I
believe the day we're at Nassau,we have a, a morning of meetings
(11:08):
and trainings and, and meetingwith Royal Caribbean.
so I'm excited for that.
Our day at sea, we're inmeetings a lot of the day, but
we also get to try some of thespecialty restaurants throughout
the day, so
ryan_2_10-31-2025_1450 (11:18):
Awesome.
j_1_10-31-2025_145008 (11:19):
for that.
and then of course we havePerfect Day Coco K, we are
getting a tour of the island.
And then I have booked us forHideaway Beach.
I wasn't gonna do that'cause Ijust wasn't sure if I wanted to
spend the extra and you know,would we have time?
But then I kind of thought, whenelse are we going to be going on
(11:41):
a careers without children that
ryan_2_10-31-2025_145008 (11:42):
Yeah.
j_1_10-31-2025_145008 (11:42):
to Hideaway Beach?
ryan_2_10-31-2025_145008 (11:44):
even if you just go for a couple
hours after you're done withyour stuff, I still think it's
worth the price.
j_1_10-31-2025_145008 (11:49):
yeah, absolutely.
Steven's not going on the tour,so he can go hang out at
Hideaway Beach
ryan_2_10-31-2025_145008 (11:53):
Yeah.
j_1_10-31-2025_145008 (11:54):
I will be working a lot on that trip.
So Steven is also planning onworking a lot on that trip, and
that's how we're, justifyingthis one.
ryan_2_10-31-2025_145008 (12:01):
Okay.
we will be anxiously awaiting tohear how much work you and
Steven actually get done on youradults only crews
j_1_10-31-2025_145008 (12:09):
I'm excited.
ryan_2_10-31-2025_145008 (12:10):
we love learning about where our
clients are traveling, even whenwe're the clients.
That's part of the fun, and wealso love to highlight them on
the podcast.
So who knows?
Maybe if you work with WonderBeyond Travel, your trip will be
featured next.
All right, Julie, we are doingthe trip.
We've done the planning.
(12:32):
The number one thing is, likeyou said, set the expectations.
and I say this every time I workwith a multi-generational trip,
do not try to do everythingtogether.
If you're the Disney family of20 walking down the sidewalk, or
if you think everybody needs topick out their pool chair by 7
(12:54):
45 in the morning, you're gonnabe.
Really stressed out anddisappointed by the end of the
trip.
j_1_10-31-2025_145008 (13:01):
Yeah, that sounds exhausting.
And, you know, it sounds sotempting to, have one big plan
and we're all gonna do this andit just doesn't end up working
out.
What I've found in largergroups, especially at a place
like Disney, is you spend halfthe time waiting for people to
go to the bathroom.
As silly as that sounds
ryan_2_10-31-2025_145008 (13:22):
Oh, it doesn't sound silly at all.
Yeah.
j_1_10-31-2025_145008 (13:24):
and it's like, oh, so and so has to go.
We're gonna stop and so and so'sgonna go.
You don't have to go,
ryan_2_10-31-2025_145008 (13:28):
Yeah.
j_1_10-31-2025_145008 (13:29):
now we're gonna walk.
And then it's like, oh, now Ihave to go, or now the baby
needs to go, So just setting theexpectations that it's okay that
you're gonna do this and I'mgonna do this and we'll meet up
later.
ryan_2_10-31-2025_145 (13:39):
sometimes it's people doing stuff
separately during the day andthen meeting up for dinner.
Sometimes it's setting anevening where, the young adults
can go out and grandma andgrandpa watch the kids.
or maybe it's a time wheregrandma and grandpa get to go
out and have a date.
one of the first times I took myparents to Disney, my dad
actually found out throughsocial media.
(13:59):
That one of his high schoolfriends was staying across the
lake at another resort and hewent over and talked to him,
this family goes to Disney allthe time.
What the grandparents do is theyspend one day with each family.
So Wednesday they spend the daywith your family, and then they
spend the day with the nextfamily, and then they have a day
off.
they're rotating around.
(14:20):
They're not feeling like theyhave to be with everybody all
the time.
I kind of like that idea.
j_1_10-31-2025_145008 (14:24):
That's so interesting.
I haven't thought about doing itthat way.
I'll also mention, if you aretraveling with multiple rooms,
we can put a request in forthose rooms to be near each
other or connecting, but it isnot guaranteed.
which could be a pro or a condepending on your family.
ryan_2_10-31-2025_1 (14:41):
Absolutely.
one of the things to consider ismaybe there's meeting points,
throughout the resort.
So maybe, you know, hey, we knowthat we always meet for dinner
in the lobby, or we always knowwe meet at the pool, in this
spot.
this is the.
Exit to the, to the resort thatwe always leave from that can
really help folks.
obviously, this has changed alot with apps for the resort
(15:05):
that maybe has messaging thesame with cruises, being able to
message with the wifi at theresort or on the cruise so
people are in much more contact.
planning some of those thingsahead of time, really helps out.
I will say with all of this Asmuch as we're saying, don't try
to be together all the time.
Do plan at least a couple timeswhere everybody's together.
(15:29):
This is the time to get yourpictures.
This is the time to have a mealand say thank you to the person
that maybe has paid for thetrip.
have a couple times where youare connecting as a larger group
and take those pictures and havethat fun.
j_1_10-31-2025_145008 (15:44):
so the last big thing I don't want you
to make the mistake of is don'tmiss the little moments.
It's really fun to plan the bigmoments, to plan the big
excursions, to plan a fancy mealor to plan the big character
meal, or that we're all gonna goon this ride together.
(16:05):
But a lot of times those littlemoments are.
cousins running up to each otherwhen they first see each other
in the Magic Kingdom.
going off and doing the waterslides together at your resort,
going to a trivia session or asilent disco on your cruise
ship.
Things like that, that happenmuch more spontaneously that you
(16:26):
can't really plan.
I struggle with this, travelingwith my family and I know many
families do.
feel like you're on a scheduleto get and do the things that
you've planned in advance, andyou don't wanna miss anything.
But please make sure you slowdown, especially with a larger
group, and enjoy those littlemoments, seeing all the little
kids watching the fireworkstogether.
(16:47):
all the adults being together inone space, sharing a meal,
things that don't happen in youreveryday life.
ryan_2_10-31-2025_145008 (16:55):
I really love that.
I think that's the perfect,cherry on the top with our
discussion today when it comesto multi-gen travel.
And the last bit of advice thatI would have is if you haven't
done it and you like yourfamily, try it.
It's a lot of fun.
But notice I said if you likeyour family, the world is full
(17:16):
of wonder Your next adventure iswaiting at Wonder and Beyond
Travel.
We work with you to create a oneof a kind journey, taking the
stress off your plate so you canfocus on the joy of exploring
and the memories that will staywith you forever.
If you're ready to startplanning or you just want to
dream a little bigger, head onover to Wonder and beyond
(17:36):
travel.com, and we would love tohelp you get started.
We look forward to talking toyou next week on all Things
Travel, when we discuss onecountry, three budgets in Japan.
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