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
July 11–15, 2025 Friday to Tuesday	4 nights	Grandparents & Grandkids cruise	Angelique	Learn More
July 11–14, 2025 Friday to Monday	3 nights	Sip & Sail: Craft cocktails	J. & E. Riggin	Learn More
July 11–15, 2025 Friday to Tuesday	4 nights	Weekend Escape	Stephen Taber	Learn More
July 11–15, 2025 Friday to Tuesday	4 nights	Hiking and Island Exploration	American Eagle	Learn More
July 13–17, 2025 Sunday to Thursday	4 nights	Just sail & relax	Mary Day	Learn More
July 13–19, 2025 Sunday to Saturday	6 nights	Explore the Maine Coast	Heritage	Learn More
July 14–18, 2025 Monday to Friday	4 nights	Four-nights, no set itinerary	Ladona	Learn More
July 15–19, 2025 Tuesday to Saturday	4 nights	Lighthouses & lobster cruise	J. & E. Riggin	Learn More
July 15–19, 2025 Tuesday to Saturday	4 nights	Four-night cruise	Lewis R. French	Learn More
July 16–21, 2025 Wednesday to Monday	5 nights	Five Night Adventure	Grace Bailey	Learn More
July 16–20, 2025 Wednesday to Sunday	4 nights	Lighthouse cruise	Angelique	Learn More
July 16–20, 2025 Wednesday to Sunday	4 nights	Four-night Getaway	Stephen Taber	Learn More
July 17–22, 2025 Thursday to Tuesday	5 nights	Eastbound: Blue Hill Bay and Beyond	American Eagle	Learn More
July 18–21, 2025 Friday to Monday	3 nights	Weekend Getaway	Mary Day	Learn More
July 19–24, 2025 Saturday to Thursday	5 nights	Five-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