Skip to content or footer

Book My Trip

209 sailing adventures found.

Page 3 of 14
Dates Length Vessel
June 16–19, 2023
Friday to Monday
3 nights Father’s Day Weekend Lewis R. French
June 16–19, 2023
Friday to Monday
3 nights Father’s Day Weekend Getaway!/New Moon Mary Day
June 19–24, 2023
Monday to Saturday
5 nights Lighthouses and Shore Trips (Summer Solstice) Heritage
June 19–22, 2023
Monday to Thursday
3 nights Sip & Sail: Cocktail Craft w/Lara Nixon J. & E. Riggin
June 20–24, 2023
Tuesday to Saturday
4 nights Summer Solstice - Watercolor Workshop American Eagle
June 20–24, 2023
Tuesday to Saturday
4 nights Summer Solstice & Live Music Ladona
June 20–24, 2023
Tuesday to Saturday
4 nights Sailing and Hiking! Lewis R. French
June 20–24, 2023
Tuesday to Saturday
4 nights Lighthouse Cruise Mary Day
June 20–24, 2023
Tuesday to Saturday
4 nights Summer Solstice and Music Cruise w/Jenn Schott Stephen Taber
June 20–24, 2023
Tuesday to Saturday
4 nights Featuring Tim Grimm Grace Bailey
June 22–26, 2023
Thursday to Monday
4 nights Sawmill Creek Fiber Event J. & E. Riggin
June 24–27, 2023
Saturday to Tuesday
3 nights 3-Night Sail Ladona
June 25–July 1, 2023
Sunday to Saturday
6 nights Maritime Historian/Naturalist Angelique
June 25–July 1, 2023
Sunday to Saturday
6 nights Traces of the Past American Eagle
June 25–July 1, 2023
Sunday to Saturday
6 nights Boothbay Harbor Windjammer Festival Heritage
Page 3 of 14
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 may request a mailed packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

Request a Packet Visit the Fleet Page

You are using an outdated browser. Please upgrade your browser to improve your experience. We recommend Google Chrome.