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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.

Page 8 of 15
Dates Length Vessel
July 27–30, 2025
Sunday to Wednesday
3 nights Three-night cruise Lewis R. French
July 27–30, 2025
Sunday to Wednesday
3 nights Three-night getaway Stephen Taber
July 27–August 1, 2025
Sunday to Friday
5 nights Explore the Maine Coast Heritage
July 27–August 2, 2025
Sunday to Saturday
6 nights Unscripted Adventure American Eagle
July 30–August 2, 2025
Wednesday to Saturday
3 nights Three-night cruise Lewis R. French
July 30–August 2, 2025
Wednesday to Saturday
3 nights Three-night getaway Stephen Taber
July 31–August 4, 2025
Thursday to Monday
4 nights Eggemoggin Reach Regatta Grace Bailey
July 31–August 7, 2025
Thursday to Thursday
7 nights Ports Unknown: Secrets of the Outer Islands Ladona
August 2–6, 2025
Saturday to Wednesday
4 nights Perseid Meteor Showers Heritage
August 3–7, 2025
Sunday to Thursday
4 nights Windjammers & Watercolors cruise Angelique
August 3–8, 2025
Sunday to Friday
5 nights Music & dance cruise J. & E. Riggin
August 3–9, 2025
Sunday to Saturday
6 nights Captain's favorite harbors cruise Mary Day
August 3–9, 2025
Sunday to Saturday
6 nights Swan's Island Music Festival Lewis R. French
August 3–9, 2025
Sunday to Saturday
6 nights Captain's Choice Stephen Taber
August 3–7, 2025
Sunday to Thursday
4 nights Hiking and Island Exploration American Eagle
Page 8 of 15

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

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