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.

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Dates	Length		Vessel
August 24–30, 2025 Sunday to Saturday	6 nights	Camden Windjammer Festival	Lewis R. French	Learn More
August 24–30, 2025 Sunday to Saturday	6 nights	Camden Windjammer Festival	Heritage	Learn More
August 26–30, 2025 Tuesday to Saturday	4 nights	Camden Windjammer Festival	Grace Bailey	Learn More
August 26–30, 2025 Tuesday to Saturday	4 nights	Camden Windjammer Festival	J. & E. Riggin	Learn More
August 26–30, 2025 Tuesday to Saturday	4 nights	Camden Windjammer Festival	Mary Day	Learn More
August 26–31, 2025 Tuesday to Sunday	5 nights	Full - private charter	Ladona	Learn More
August 27–31, 2025 Wednesday to Sunday	4 nights	Camden Windjammer Festival	Stephen Taber	Learn More
August 27–September 4, 2025 Wednesday to Thursday	8 nights	Gloucester Schooner Festival & Race	American Eagle	Learn More
August 31–September 6, 2025 Sunday to Saturday	6 nights	Music + Sailing Six Night Adventure	Grace Bailey	Learn More
August 31–September 6, 2025 Sunday to Saturday	6 nights	Six-night Labor Day cruise	Angelique	Learn More
August 31–September 6, 2025 Sunday to Saturday	6 nights	Maine knitting getaway	J. & E. Riggin	Learn More
August 31–September 1, 2025 Sunday to Monday	1 nights	One-night Staycation cruise	Mary Day	Learn More
August 31–September 6, 2025 Sunday to Saturday	6 nights	Explore the Maine Coast	Heritage	Learn More
September 1–5, 2025 Monday to Friday	4 nights	Music w/Chicky Stoltz & Ragged Co.	Stephen Taber	Learn More
September 1–7, 2025 Monday to Sunday	6 nights	Six-nights; no set itinerary	Ladona	Learn More

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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