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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 11 of 15
Dates Length Vessel
August 23–25, 2025
Saturday to Monday
2 nights Available for private charter! Ladona
August 24–30, 2025
Sunday to Saturday
6 nights Camden Windjammer Festival Angelique
August 24–30, 2025
Sunday to Saturday
6 nights Camden Windjammer Festival Lewis R. French
August 24–30, 2025
Sunday to Saturday
6 nights Camden Windjammer Festival Heritage
August 26–30, 2025
Tuesday to Saturday
4 nights Camden Windjammer Festival hosted by Marc Evan Jackson Grace Bailey
August 26–30, 2025
Tuesday to Saturday
4 nights Camden Windjammer Festival J. & E. Riggin
August 26–30, 2025
Tuesday to Saturday
4 nights Camden Windjammer Festival Mary Day
August 26–31, 2025
Tuesday to Sunday
5 nights Full - private charter Ladona
August 27–31, 2025
Wednesday to Sunday
4 nights Camden Windjammer Festival Stephen Taber
August 27–September 4, 2025
Wednesday to Thursday
8 nights Gloucester Schooner Festival & Race American Eagle
August 31–September 6, 2025
Sunday to Saturday
6 nights Music + Sailing Six Night Adventure Grace Bailey
August 31–September 6, 2025
Sunday to Saturday
6 nights Six-night Labor Day cruise Angelique
August 31–September 6, 2025
Sunday to Saturday
6 nights Maine knitting getaway J. & E. Riggin
August 31–September 1, 2025
Sunday to Monday
1 nights One-night Staycation cruise Mary Day
August 31–September 6, 2025
Sunday to Saturday
6 nights Explore the Maine Coast Heritage
Page 11 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

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