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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 13 of 15
Dates Length Vessel
September 14–18, 2025
Sunday to Thursday
4 nights Sip & Sail: Craft cocktails J. & E. Riggin
September 14–18, 2025
Sunday to Thursday
4 nights Just sail & relax Mary Day
September 14–20, 2025
Sunday to Saturday
6 nights Wine, Dine and Cheese tasting Stephen Taber
September 14–17, 2025
Sunday to Wednesday
3 nights Lobsters, sailing and music Heritage
September 14–19, 2025
Sunday to Friday
5 nights Fall Eastbound (Booked for private charter) American Eagle
September 14–18, 2025
Sunday to Thursday
4 nights Full - private charter Ladona
September 18–21, 2025
Thursday to Sunday
3 nights Three-night cruise Lewis R. French
September 19–22, 2025
Friday to Monday
3 nights Three Night Adventure Hosted by Marc Evan Jackson Grace Bailey
September 19–23, 2025
Friday to Tuesday
4 nights Lighthouses & lobster cruise J. & E. Riggin
September 19–22, 2025
Friday to Monday
3 nights Fall weekend getaway Mary Day
September 19–23, 2025
Friday to Tuesday
4 nights Autumn on the Bay Ladona
September 20–26, 2025
Saturday to Friday
6 nights Explore the Maine Coast Heritage
September 21–27, 2025
Sunday to Saturday
6 nights Six-night cruise with naturalist on board Angelique
September 21–25, 2025
Sunday to Thursday
4 nights Autumn on the Bay Stephen Taber
September 21–25, 2025
Sunday to Thursday
4 nights Celtic Isles American Eagle
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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

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