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Book My Trip

Use the “Book My Trip” box above to search for cruise dates. Cruises end in mid-October and begin again in May. You can also find each vessel’s schedule by visiting their fleet page.

203 sailing adventures found.

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Dates Length Vessel
October 2–6, 2023
Monday to Friday
4 nights Sip & Sail: Cocktail Craft w/Lara Nixon J. & E. Riggin
October 4–7, 2023
Wednesday to Saturday
3 nights Fall Colors Ladona
October 5–9, 2023
Thursday to Monday
4 nights 4-Night Fall Colors Cruise Stephen Taber
October 5–9, 2023
Thursday to Monday
4 nights Fall Foliage Grace Bailey
October 6–9, 2023
Friday to Monday
3 nights Weekend Foliage Cruise Angelique
October 6–9, 2023
Friday to Monday
3 nights Cool Days and Cozy Nights American Eagle
October 7–11, 2023
Saturday to Wednesday
4 nights Fall Foliage Cruise J. & E. Riggin
October 9–12, 2023
Monday to Thursday
3 nights Fall Colors Ladona
October 10–14, 2023
Tuesday to Saturday
4 nights That's It For 2023! American Eagle
October 10–13, 2023
Tuesday to Friday
3 nights 3-Night Fall Colors Cruise Stephen Taber
October 13–16, 2023
Friday to Monday
3 nights Fall Colors Ladona
May 20–23, 2024
Monday to Thursday
3 nights Shakedown cruise J. & E. Riggin
May 23–27, 2024
Thursday to Monday
4 nights Wine, dine and chocolate Stephen Taber
May 24–27, 2024
Friday to Monday
3 nights available for private charter - please inquire Angelique
May 24–28, 2024
Friday to Tuesday
4 nights Live music 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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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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