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/4byBC2Z
- Insect Bite Healer (this little gadget is amazing - we use this one the most to deal with bug bites): https://amzn.to/4gvhkuH
- All 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/18500617
- Part 2: Maine Island Hopping on a Windjammer Sailing Cruise: https://www.buzzsprout.com/2448059/episodes/18537898
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.
