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.

216 sailing adventures found.

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Dates	Length		Vessel
June 22–28, 2025 Sunday to Saturday	6 nights	Natural history and photography cruise	Mary Day	Learn More
June 22–25, 2025 Sunday to Wednesday	3 nights	Three-night cruise	Lewis R. French	Learn More
June 22–26, 2025 Sunday to Thursday	4 nights	Culinary Explorations	Stephen Taber	Learn More
June 22–28, 2025 Sunday to Saturday	6 nights	Murder Mystery Tour	Heritage	Learn More
June 22–25, 2025 Sunday to Wednesday	3 nights	Three-nights; no set itinerary	Ladona	Learn More
June 24–28, 2025 Tuesday to Saturday	4 nights	Sip & Sail: Craft beers	J. & E. Riggin	Learn More
June 25–28, 2025 Wednesday to Saturday	3 nights	Main Sails and Lobster Tails	American Eagle	Learn More
June 25–29, 2025 Wednesday to Sunday	4 nights	Full - private charter	Ladona	Learn More
June 26–29, 2025 Thursday to Sunday	3 nights	Three-night cruise	Lewis R. French	Learn More
June 28–July 5, 2025 Saturday to Saturday	7 nights	Great Schooner Race	Stephen Taber	Learn More
June 29–July 5, 2025 Sunday to Saturday	6 nights	The Great Schooner Race	Grace Bailey	Learn More
June 29–July 5, 2025 Sunday to Saturday	6 nights	Great Schooner Race	Angelique	Learn More
June 29–July 5, 2025 Sunday to Saturday	6 nights	Great Schooner Race	J. & E. Riggin	Learn More
June 29–July 5, 2025 Sunday to Saturday	6 nights	Great Schooner Race	Mary Day	Learn More
June 29–July 5, 2025 Sunday to Saturday	6 nights	4th of July Celebrations & Schooner Race	Heritage	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