Skip to content or footer

Find My Trip

Use the “Book My Trip” box above to search for cruise dates. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page.

217 sailing adventures found.

Page 6 of 15
Dates Length Vessel
July 11–15, 2025
Friday to Tuesday
4 nights Four Night Adventure Hosted by Marc Evan Jackson Grace Bailey
July 11–15, 2025
Friday to Tuesday
4 nights Grandparents & Grandkids cruise Angelique
July 11–14, 2025
Friday to Monday
3 nights Sip & Sail: Craft cocktails J. & E. Riggin
July 11–14, 2025
Friday to Monday
3 nights Three-night cruise Lewis R. French
July 11–15, 2025
Friday to Tuesday
4 nights Weekend Escape Stephen Taber
July 11–15, 2025
Friday to Tuesday
4 nights Hiking and Island Exploration American Eagle
July 13–17, 2025
Sunday to Thursday
4 nights Just sail & relax Mary Day
July 13–19, 2025
Sunday to Saturday
6 nights Explore the Maine Coast Heritage
July 14–18, 2025
Monday to Friday
4 nights Four-nights, no set itinerary Ladona
July 15–19, 2025
Tuesday to Saturday
4 nights Lighthouses & lobster cruise J. & E. Riggin
July 15–19, 2025
Tuesday to Saturday
4 nights Four-night cruise Lewis R. French
July 16–21, 2025
Wednesday to Monday
5 nights Five Night Adventure Grace Bailey
July 16–20, 2025
Wednesday to Sunday
4 nights Lighthouse cruise Angelique
July 16–20, 2025
Wednesday to Sunday
4 nights Four-night Getaway Stephen Taber
July 17–22, 2025
Thursday to Tuesday
5 nights Eastbound: Blue Hill Bay and Beyond American Eagle
Page 6 of 15

Trying to book last minute?

You can find cabin availability on each vessel’s website. OR, use this form to let us know when you’re hoping to sail, how many people are in  your party and what length trip you’re looking for. This form goes to all our member vessels at once. Any of the windjammers that can accommodate you will get back to you with cabin availability asap!

Please note: We do our best to keep trip schedules as up-to-date as possible, however schedules are subject to change. We also do not track cabin availability on the Maine Windjammer Association website. For cabin availability or to confirm a specific sail date, please contact the vessel directly.

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

Monthly Newsletter Signup

Brochures

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

Request a Packet Visit the Fleet Page

You are using an outdated browser. Please upgrade your browser to improve your experience. We recommend Google Chrome.