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.

181 sailing adventures found.

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Dates	Length		Vessel
July 31–August 7, 2025 Thursday to Thursday	7 nights	Ports Unknown: Secrets of the Outer Islands	Ladona	Learn More
August 2–6, 2025 Saturday to Wednesday	4 nights	Perseid Meteor Showers	Heritage	Learn More
August 3–7, 2025 Sunday to Thursday	4 nights	Windjammers & Watercolors cruise	Angelique	Learn More
August 3–8, 2025 Sunday to Friday	5 nights	Maine Knitting Retreat	J. & E. Riggin	Learn More
August 3–9, 2025 Sunday to Saturday	6 nights	Captain's favorite harbors cruise	Mary Day	Learn More
August 3–9, 2025 Sunday to Saturday	6 nights	Swan's Island Music Festival	Lewis R. French	Learn More
August 3–9, 2025 Sunday to Saturday	6 nights	Captain's Choice	Stephen Taber	Learn More
August 3–7, 2025 Sunday to Thursday	4 nights	Hiking and Island Exploration	American Eagle	Learn More
August 5–9, 2025 Tuesday to Saturday	4 nights	Four Night Adventure	Grace Bailey	Learn More
August 7–10, 2025 Thursday to Sunday	3 nights	Perseid Meteor Showers	Heritage	Learn More
August 8–13, 2025 Friday to Wednesday	5 nights	Perseid Meteor Shower	Angelique	Learn More
August 8–11, 2025 Friday to Monday	3 nights	Perseid Meteor Showers	American Eagle	Learn More
August 8–11, 2025 Friday to Monday	3 nights	Full - private charter	Ladona	Learn More
August 9–13, 2025 Saturday to Wednesday	4 nights	Perseids meteor shower	J. & E. Riggin	Learn More
August 10–16, 2025 Sunday to Saturday	6 nights	Six 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