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
September 23–27, 2025 Tuesday to Saturday	4 nights	Four Night Adventure	Grace Bailey	Learn More
September 23–27, 2025 Tuesday to Saturday	4 nights	Fall foliage!	Mary Day	Learn More
September 24–28, 2025 Wednesday to Sunday	4 nights	Sip & Sail: Craft cocktails of Maine	J. & E. Riggin	Learn More
September 24–28, 2025 Wednesday to Sunday	4 nights	Autumn on the Bay	Ladona	Learn More
September 26–30, 2025 Friday to Tuesday	4 nights	Autumn on the Bay	Stephen Taber	Learn More
September 26–30, 2025 Friday to Tuesday	4 nights	Autumn on the Bay	American Eagle	Learn More
September 27–30, 2025 Saturday to Tuesday	3 nights	Three-night cruise	Lewis R. French	Learn More
September 27–October 1, 2025 Saturday to Wednesday	4 nights	Fall Foliage	Heritage	Learn More
September 28–October 2, 2025 Sunday to Thursday	4 nights	Four Night Adventure	Grace Bailey	Learn More
September 28–October 2, 2025 Sunday to Thursday	4 nights	Foliage and lighthouse cruise	Angelique	Learn More
September 29–October 3, 2025 Monday to Friday	4 nights	Girl Camper Retreat	J. & E. Riggin	Learn More
September 29–October 3, 2025 Monday to Friday	4 nights	Fall colors	Ladona	Learn More
October 1–4, 2025 Wednesday to Saturday	3 nights	Three-night cruise	Lewis R. French	Learn More
October 1–5, 2025 Wednesday to Sunday	4 nights	Fall Colors	Stephen Taber	Learn More
October 2–5, 2025 Thursday to Sunday	3 nights	One Last Turn Around the Bay	American Eagle	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