Overnight Cruise on Grace Bailey Maine Windjammer Sailboat for a Relaxing Slow Travel Vacation

Overnight Cruise on Grace Bailey Maine Windjammer Sailboat for a Relaxing Slow Travel Vacation

Welcome to Small Ship Cruise Talk, your go-to podcast—and the only podcast of its kind—for all things small ship cruising! Whether you're curious about river cruises, yacht cruises, expedition cruises, barge cruises, or ship-within-a-ship experiences on larger vessels, we, Dan and Mikkel, of the esteemed small ship cruise website Sometimes Sailing, have you covered. Ever wondered what it’s like to sail on a ship with just four passengers...or 150? Want to know how to budget for a small ship cruise and what the actual costs are? Do we give small ship cruise food a thumbs up or thumbs down? Find out all that and more, like what kinds of ports small ships go to and what packing essentials we recommend, along with valuable small ship cruise travel planning tips. Each episode delivers concise, value-packed insights to help you easily navigate the world of luxury, adventure, and intimate cruising. Join us as we dive into real cruise experiences, insider tips, and expert interviews to help you plan your perfect small ship vacation. Instagram, Threads, & Pinterest: @sometimessailing

Episodes

July 15, 2026 34 mins

We spent three nights aboard Grace Bailey, a historic schooner in the Maine Windjammer fleet, and we're breaking down everything you need to know for consideration before booking your trip. 

From the small cabin to the beach lobster bake (s'mores included), we share what daily life actually looks like on a 19th-century sailing ship with no Wi-Fi, no fixed itinerary, and the ship's cat, named Fiji, who steals the show.

Join us to...

Listen
Watch
Mark as Played

Join us for a lively recap of the 🇺🇸 July 4th celebrations in New York City, as seen from Governors Island and at home, focusing on the historic maritime events, the Parade of Sail, and the significance of waterway traditions. 

Discover how media coverage, Native American acknowledgment, and sustainability narratives intertwined in this special episode.

Related listening: 

  • Sail4th 250 in NYC - Once-in-a-Lifetim...
Listen
Watch
Mark as Played

⚓️ Dreaming of a cruise but not sure how to make it happen financially? 💭 That dream cruise doesn't have to stay a dream. 

We sit down with Danielle Desir Corbett of The Thought Card to break down a realistic, stress-free system for saving for your dream cruise in a year or less — from building your travel fund to finding money you didn't know you had, and how to stay the course when life gets in the way. 

Find &...

Listen
Watch
Mark as Played

We're taking you aboard American Cruise Lines' Southeast Sea Islands itinerary — a nine-day, eight-night coastal cruise through the Intracoastal Waterway on a brand-new coastal catamaran, the American Liberty. If you've only thought of ACL as a river cruise line, this one might surprise you.

We cover the ship (what makes a coastal catamaran different and how it compares to ACL's river vessels), the ports, when to go, and how t...

Listen
Watch
Mark as Played

🇺🇸 America turns 250 this July 4th, and New York Harbor is throwing the biggest nautical celebration in a generation. We're breaking down everything you need to know about Sail4th 250 — the historic Parade of Sails for the USA's semiquincentennial, happening on July Fourth in the Hudson River next to Manhattan, including events from July 3rd to 6th, 2026.

We sat down with William Armstrong, Communications Director for Sail4t...

Listen
Watch
Mark as Played

Celebrity River Cruises is making waves before launching, and we're breaking down the four excursion categories that make up their new Destination Discovery program to see if it lives up to the hype.

We cover the:

  • Storyteller Series - locally-led experiences with cultural insiders
  • Skillmaster Series - hands-on time with local makers and artisans
  • Keys to the City - a self-guided digital platform with stationed local hosts. A hotspot...
Listen
Watch
Mark as Played

Curious about Road Scholar travel programs, but not sure if it's right for you? This episode gives you everything you need to know about the cruise trips (called “Afloat” programs) with Road Scholar, a prestigious non-profit travel company.

We hear directly from Zoe Fox-Mailer, Director of Programming at Road Scholar, on exactly how the Adventure Afloat program works — how trips are structured, what a typical day l...

Listen
Watch
Mark as Played

Ever had that pull to go back to a cruise you loved? 

We're breaking down exactly what to consider before you rebook, from choosing the same cruise line vs. switching it up, to how time of year, ports, and even a different version of yourself can make the same river feel brand new. 

Plus, we share our own experience returning to AmaWaterways' Colors of Provence and what's making us excited to see it through fresh eyes.

We co...

Listen
Watch
Mark as Played

The future of cruising is looking bright, and we have the inside scoop straight from Seatrade Miami, the cruise industry's leading global event. In this episode, we share our six biggest takeaways, from the explosive growth of river cruising and the rising appeal of expedition and yacht cruises, to why small ships are winning over first-time travelers in a big way.

We also get into what's new in onboard drinks (including gluten-free...

Listen
Watch
Mark as Played

Ever struggle to hear your tour guide on a shore excursion, or find that uncomfortable single-use earpiece driving you crazy? 

We're breaking down everything you need to know about the #1 listening device for cruise tours, called a Quietvox—the small audio device you'll find in your stateroom on most small ship cruises. We’re explaining how it works to deliver your guide's commentary directly to your ear and tips yo...

Listen
Watch
Mark as Played

Is it dumb to take a boating excursion during a vacation when you’re already on a cruise? Today, we answer this question with the pros, cons, and things you may not have thought of! Ultimately, we’re going to help you decide if your answer is yes or no. 

We’re also sharing what kinds of boating excursions are out there, from sunset sails to dolphin spotting, whale watching, SCUBA and snorkeling, alligator adve...

Listen
Watch
Mark as Played

We’re back with Part 2 of our Tennessee Rivers cruise with American Cruise Lines (ACL)—diving into the ports, excursions, and what surprised us most along the way as we sailed on the Tennessee, Cumberland, and Ohio Rivers. 

From Chattanooga to Nashville, we share the excursion options along the way, including scenic sailing, small-town gems, Civil War history, and unique stops like the U.S. Space & Rocket Center...

Listen
Watch
Mark as Played

You’re going to love this two-part series about our Tennessee River cruise with American Cruise Lines from Chattanooga to Nashville!

We’re talking about the big picture of the experience in Part 1: What a Tennessee River cruise is like (including sailing on the Ohio River and Cumberland River), who this cruise is best for, what the American river cruise ship experience is like, and what surprised us about cruising throug...

Listen
Watch
Mark as Played

We sit down with travel journalist Joel Balsam to explore what sustainability really looks like in cruising today. From Norway’s electric-first mindset to Havila’s hybrid ships powered by biogas and massive battery systems, we unpack how innovation is reshaping the industry.

We share how this directly impacts your experience—quieter, near-silent sailing through pristine landscapes, more intentional dining that redu...

Listen
Watch
Mark as Played

What do you do when you need clean clothes on a cruise? In this episode, we break down the three ways to handle laundry while sailing: self-serve washers and dryers, onboard send-away laundry service, and simple DIY options, like handwashing. 

We also share cruise line differences you should check before packing, why some ships don’t offer laundry at all while others unexpectedly do, and a few travel items that make washi...

Listen
Watch
Mark as Played

River cruising sounds simple—but first-timers are often surprised once they step onboard. We’re sharing five common mistakes we see again and again, from choosing the wrong cruise line to packing the wrong items, plus a few myths that stop travelers from booking in the first place.

You’ll learn how to compare top lines like Viking, AmaWaterways, Avalon, Uniworld, Emerald Cruises, and Riverside Luxury Cruises, why s...

Listen
Watch
Mark as Played

Come along to delve further into a “tale of two cruises” as we chat with travel expert and small-ship cruise enthusiast Tamara Gruber about her barge cruises through France’s small waterways and a Maine Windjammer cruise aboard schooner Heritage, sailing along the coast of Maine.

We compare how these intimate experiences are similar and how they’re completely different, from daily life onboard to who the idea...

Listen
Watch
Mark as Played

Travel should feel freeing, not stressful. With that in mind, to best prepare you for your travels and smooth sailing, we are sharing four common travel scams that can happen on cruise itineraries on land or purely during your land vacation, and the simple habits that stop them. 

You’ll learn why these scams work and what to do instead so you have peace of mind. 

During this episode, we reference the following items t...

Listen
Watch
Mark as Played

We’re sharing an exclusive first look at Windstar’s Star Seeker after attending her christening and touring the ship in Miami. We'll give you a "guided tour" so you can decide if this new-build ship is right for your next cruise.

Star Seeker carries just 224 guests, blending small-ship intimacy with elevated design. We talk through first impressions—from the welcoming lobby and leather-lined hallways to suites with...

Listen
Watch
Mark as Played

means for river cruising. Find out the biggest announcements so far, including early demand, booking timelines, and Celebrity’s long-term commitment to building a sizable river fleet.

Our companion article (with photos) can be found here: https://sometimessailing.com/celebrity-river-cruises

We walk through what’s confirmed for 2027 and 2028, which region these ships will sail in, and which iconic rivers and seasonal itine...

Listen
Watch
Mark as Played

Popular Podcasts

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    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

    Betrayal Weekly

    Betrayal Weekly is back for a new season. Every Thursday, Betrayal Weekly shares first-hand accounts of broken trust, shocking deceptions, and the trail of destruction they leave behind. Hosted by Andrea Gunning, this weekly ongoing series digs into real-life stories of betrayal and the aftermath. From stories of double lives to dark discoveries, these are cautionary tales and accounts of resilience against all odds. From the producers of the critically acclaimed Betrayal series, Betrayal Weekly drops new episodes every Thursday. If you would like to share your story, you can reach out to the Betrayal Team by emailing them at betrayalpod@gmail.com and follow us on Instagram at @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    QUESTION EVERYTHING

    There are celebrity interviews, and there are life-changing conversations. On Question Everything, you get both. Journalist Danielle Robay has a rare gift: she makes people feel safe + seen enough to tell the truth. Every week, she draws out the stories the world's most fascinating people rarely get to tell– the heartbreaks, the risks, the controversies, the beliefs they had to unlearn to become who they are and every now and then, their thoughts on the Bravoverse. You'll come for their story. You'll leave rethinking your own. -------- Danielle is also the creator of the bestselling QUESTION EVERYTHING card game series, which has sparked connection in thousands of living rooms around the world, and the co-executive producer and host of Bookmarked by Reese's Book Club, alongside Reese Witherspoon. Dubbed "The Queen of Questions," she brings both heart and rigor to every conversation — a background in political science, a Gloria Steinem Fellowship, and a mentorship under Larry King, whose legacy of curiosity and connection she's carried forward across more than 8,000 hours of interviews with icons from Taylor Swift to Malala Yousafzai.

Advertise With Us
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