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

Dan and Mikkel Woodruff
  • 5.0 (13)
  • Places & Travel
  • Updated Biweekly

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

  1. Jul 15

    Our Maine Windjammer Vacation on Historic Sailboat, Grace Bailey

    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 learn about the accommodations, food, and the realities of sleeping below deck crew traffic — plus what to pack, how the honor-system doors work, and why carabiners became our best friend on board. We also get into the cost, from the per-person price to the Maine resident discount, and explain why Grace Bailey's "Captain's Choice" itinerary means no two cruises look the same. If you've never considered a Maine Windjammer cruise, or didn't know they existed, this episode will help you decide if slow, unplugged sailing is for you. Helpful resources from this episode: Maine Windjammer Packing List: https://sometimessailing.com/printable-maine-windjammer-packing-list/Bug Bite Thing (doesn’t require batteries): https://amzn.to/4byBC2ZInsect Bite Healer (this little gadget is amazing - we use this one the most to deal with bug bites): https://amzn.to/4gvhkuHAll About Stonington Maine (a port town on many Maine Windjammer cruises): https://sometimessailing.com/things-to-do-in-stonington-maine/Foods Maine is Known For (blueberries, lobster, hot dogs, & more): https://sometimeshome.com/food-maine-is-known-for/Listen to our additional Maine Windjammer Cruise episodes:  Part 1: Sailing Cruises on Historic Maine Windjammer Ships: https://www.buzzsprout.com/2448059/episodes/18500617Part 2: Maine Island Hopping on a Windjammer Sailing Cruise: https://www.buzzsprout.com/2448059/episodes/18537898Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

    Our Maine Windjammer Vacation on Historic Sailboat, Grace Bailey

  2. Jul 10

    Bonus: Historic Maritime Event Recap from Sail4th 250 in NYC

    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-Lifetime Flotilla featuring Two Historic Maine Windjammer Cruise Ships: https://www.buzzsprout.com/2448059/episodes/19344675Part 1: Sailing Cruises on Historic Maine Windjammer Ships: https://www.buzzsprout.com/2448059/episodes/18500617Part 2: Maine Island Hopping on a Windjammer Sailing Cruise: https://www.buzzsprout.com/2448059/episodes/18537898Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

    Bonus: Historic Maritime Event Recap from Sail4th 250 in NYC

  3. Jul 1

    How to Budget and Save for a Cruise in a Year (or Less) with Danielle Corbett

    ⚓️ 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 & Follow Danielle: • Danielle's website: https://thoughtcard.com/ • The Thought Card podcast: https://thoughtcard.com/podcast/ • Instagram: https://www.instagram.com/thedaniellecorbett • Threads: https://www.threads.com/@thedaniellecorbett 📖 Get Danielle's Books:  We Are Financially Savvy Travelers: https://amzn.to/4b0Ob6Y​​ Affording Travel: https://amzn.to/4vMAjp4💰Helpful money apps and programs to help make your cruise wishes come true, mentioned during the episode: Monarch: get 50% off using our signup link: https://sometimessailing.com/monarchRakuten: sign up with our link, get $50 – https://sometimessailing.com/rakuten Fetch: https://fetch.com/  – use INVITE CODE: TMEK67 (**must be used when you sign up, before you snap your first receipt**)Travel insurance: https://sometimessailing.com/tr-insure Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

    How to Budget and Save for a Cruise in a Year (or Less) with Danielle Corbett

  4. Jun 17

    Cruising the Southeast Sea Islands on American Cruise Lines

    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 to get there — including a practical tip about open-jaw itineraries that fellow passengers clued us in on. The ports — Amelia Island, Jekyll Island, Savannah, Hilton Head, Beaufort, and Charleston — each brought something different, and the scenery sailing through the Low Country marshes was stunning. We also get into the excursions worth booking and wrap up with honest thoughts on who this cruise is really ideal for and whether the price is worth it. Links from this episode:  🍽️ See everything we ate during this cruise on our YouTube channel (don’t forget to subscribe!): https://youtu.be/IZKbztkTJOg 👀 These are the best binoculars for your travels: https://sometimessailing.com/best-binoculars-for-alaska-antarctica-cruise-leupold-bx-2-alpine-hd-review/ For more episodes about American Cruise Lines:  Listen to our Tennessee River Cruise episode: https://www.buzzsprout.com/2448059/episodes/18904212All About USA River Cruises with American Cruise Lines: https://www.buzzsprout.com/2448059/episodes/17477271Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

  5. Jun 15

    Bonus: NYC Sail4th 250, Once-in-a-Lifetime Flotilla featuring Two Historic Maine Windjammer Cruise Ships

    🇺🇸 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 Sail4th 250, and Captain Tyler of  American Eagle — one of two Maine Windjammer schooners sailing in the Parade alongside Angelique.  We cover what makes this event so rare, how 5 years of international coordination made it happen, and why a ship from India is sailing over 12,000 miles just to be there. Whether you're heading to New York in person or watching on NBC, we've got you covered: where to watch from shore, how to bring your own boat into the harbor, which ships to look for, and how to track every tall ship in real time using the Aqua Map app. We also share what it means to us personally, including why Mikkel has been dreaming about this moment since childhood, as she looks at a 1976 flotilla poster on her parents' wall. 🦅 Find out what it's like to sail on American Eagle: Part 1: Sailing Cruises on Historic Maine Windjammer Ships: https://sometimessailing.com/gczo Part 2: Maine Island Hopping on a Windjammer Sailing Cruise: https://sometimessailing.com/8xhm Maine Windjammer firsthand accounts, our website, with photos: https://sometimessailing.com/category/cruise-lines/maine-windjammer/🔗 Links mentioned in this episode: Sail4th 250 event https://sail4th.org/ & the Tall Ships "encyclopedia" https://sail4th.org/tall-shipsAqua Map app for iPhone - https://apps.apple.com/us/app/aqua-map-boating/id919552329  — or Android — https://play.google.com/store/apps/details?id=com.gec.MarineApp.WorldViewerLite&hl=en_US🇺🇸 Subscribe and follow! We'll be back after July 4th with a live recap episode. Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

  6. Jun 3

    Celebrity River Cruises: Excursion Updates

    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 insidersSkillmaster Series - hands-on time with local makers and artisansKeys to the City - a self-guided digital platform with stationed local hosts. A hotspot and battery pack are likely essential for this type of experience. Our favorite battery pack is this: https://amzn.to/4uiKG2C – and our essential hotspot is explained here: https://sometimessailing.com/6nm8  Celebrity Takeover Series - one private, exclusive event per sailingWe share our honest take on whether this is a genuine shift toward immersive river cruising or clever marketing,  and where we think the real operational challenges lie. We also touch on what's included in the base fare, how gratuities work, pre- and post-cruise stay options in Prague, Budapest, and Amsterdam, and what details we're still waiting on before the 2027 debut. If you're watching Celebrity River Cruises — whether you've already booked or you're on the fence — this episode is your update. Helpful links from this episode include: Celebrity River Cruises: Early Insights & Expectations podcast episode Audio version:  https://www.buzzsprout.com/2448059/episodes/18599836 YouTube version: https://youtu.be/oP_tGXG7ixIUtilize Mikkel's Travel Planning services: https://sometimessailing.com/au63See renderings of the Celebrity River Cruise ships on our website: https://sometimessailing.com/celebrity-cruises-makes-waves-ocean-cruise-line-enters-the-river-cruise-market/  Book tickets for a private concert in Vienna: https://sometimessailing.com/dhhs Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

  7. May 20

    All About Road Scholar Afloat: A Unique Cruise Travel Program

    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 looks like, how the floating campus model creates a real learning experience without feeling like a classroom, and how solo travelers are set up to actually connect with people.  If you've ever wondered what separates a Road Scholar cruise from just booking any small ship sailing, this conversation answers that. Then Wendy Baldwin — a Road Scholar veteran with 22+ programs completed — shares what it's actually like to be on these trips as a solo traveler. She's cruised to Holland, Greenland, Scotland, Antarctica, and Norway with Road Scholar, and she's headed to Patagonia next!  More importantly, she was skeptical of group travel before her first program. If you are too, you'll want to hear what changed her mind. By the end of this episode, you'll know whether Road Scholar is the right fit for the way you want to travel. Check out the Road Scholar Facebook groups: https://sometimessailing.com/RS-FB Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

    All About Road Scholar Afloat: A Unique Cruise Travel Program

  8. May 6

    Repeating the Same Cruise Itinerary: How to Do It Right

    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 cover: Cruising on the same line vs. a new oneWhen ports aren't the same twiceSeasonal timingThemed departuresManaging expectations of yourself, family and friendsVisa and logistics traps to avoidAnd practical tips to consider before you bookDownload our free worksheet to decide if repeating a cruise itinerary is right for you: https://sometimes-sailing.myflodesk.com/i0ol4p9hg9 Send us Fan Mail Support the show 👉🏻 Press that FOLLOW button so you never miss an episode, released every other Wednesday.  Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/ ▶️ Subscribe to our YouTube channel: @sometimes-sailing 📩 Sign up for our newsletter. 🌏 SometimesSailing.com has even more planning tips, firsthand experiences, & advice.   📱 Have questions or topic suggestions? Contact us. ©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.

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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

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