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
June 29–July 5, 2025 Sunday to Saturday	6 nights	Great Schooner Race - FULL -private charter	American Eagle	Learn More
June 30–July 5, 2025 Monday to Saturday	5 nights	Great Schooner Race	Lewis R. French	Learn More
June 30–July 5, 2025 Monday to Saturday	5 nights	Great Schooner Race	Ladona	Learn More
July 6–10, 2025 Sunday to Thursday	4 nights	Four Night Adventure	Grace Bailey	Learn More
July 6–10, 2025 Sunday to Thursday	4 nights	Grandparents & Grandkids cruise	Angelique	Learn More
July 6–10, 2025 Sunday to Thursday	4 nights	Lighthouses & lobster cruise	J. & E. Riggin	Learn More
July 6–12, 2025 Sunday to Saturday	6 nights	No Smoking Cruise	Mary Day	Learn More
July 6–9, 2025 Sunday to Wednesday	3 nights	Classic Maine Windjamming	Lewis R. French	Learn More
July 6–10, 2025 Sunday to Thursday	4 nights	Four-nights w/Kate Schaffer of Ragged Coast Chocolates	Stephen Taber	Learn More
July 6–9, 2025 Sunday to Wednesday	3 nights	Lobsters, sailing and music	Heritage	Learn More
July 6–10, 2025 Sunday to Thursday	4 nights	Coastline Classics	American Eagle	Learn More
July 6–13, 2025 Sunday to Sunday	7 nights	Ports Unknown: Secrets of Mt. Desert Island	Ladona	Learn More
July 9–12, 2025 Wednesday to Saturday	3 nights	Lobsters, sailing and music	Heritage	Learn More
July 10–14, 2025 Thursday to Monday	4 nights	FULL- private charter	Lewis R. French	Learn More
July 11–15, 2025 Friday to Tuesday	4 nights	Four Night Adventure	Grace Bailey	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