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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.

214 sailing adventures found.

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Dates Length Vessel
September 24–28, 2024
Tuesday to Saturday
4 nights Four-night adventure Grace Bailey
September 25–29, 2024
Wednesday to Sunday
4 nights Scenic Maine Photography cruise J. & E. Riggin
September 25–29, 2024
Wednesday to Sunday
4 nights Four-night cruise Ladona
September 25–29, 2024
Wednesday to Sunday
4 nights That's it for 2024! American Eagle
September 27–October 1, 2024
Friday to Tuesday
4 nights Autumn on the Bay Stephen Taber
September 28–October 1, 2024
Saturday to Tuesday
3 nights Lobsters, sailing and music Heritage
September 29–October 3, 2024
Sunday to Thursday
4 nights Lighthouse and foliage cruise Angelique
September 29–October 5, 2024
Sunday to Saturday
6 nights Six-night cruise Lewis R. French
September 29–October 3, 2024
Sunday to Thursday
4 nights Fall Foliage Four-night adventure Grace Bailey
September 30–October 4, 2024
Monday to Friday
4 nights Maine Lighthouses and Lobsters J. & E. Riggin
September 30–October 4, 2024
Monday to Friday
4 nights Fall colors cruise Ladona
October 3–7, 2024
Thursday to Monday
4 nights Fall Colors Stephen Taber
October 4–7, 2024
Friday to Monday
3 nights Weekend foliage cruise Angelique
October 4–8, 2024
Friday to Tuesday
4 nights Fall Foliage Four-night adventure Grace Bailey
October 5–9, 2024
Saturday to Wednesday
4 nights Fall foliage cruise J. & E. Riggin
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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.

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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!

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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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