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.

207 sailing adventures found.

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Dates	Length		Vessel
September 20–24, 2024 Friday to Tuesday	4 nights	Maine Lighthouses and Lobsters	J. & E. Riggin	Learn More Open in New Tab
September 20–23, 2024 Friday to Monday	3 nights	Fall weekend getaway	Mary Day	Learn More Open in New Tab
September 20–24, 2024 Friday to Tuesday	4 nights	Four-night cruise	Ladona	Learn More Open in New Tab
September 20–23, 2024 Friday to Monday	3 nights	Three-night adventure hosted by Marc Evan Jackson	Grace Bailey	Learn More Open in New Tab
September 21–27, 2024 Saturday to Friday	6 nights	Explore the Maine Coast	Heritage	Learn More Open in New Tab
September 22–28, 2024 Sunday to Saturday	6 nights	Six-night cruise	Angelique	Learn More Open in New Tab
September 22–26, 2024 Sunday to Thursday	4 nights	Autumn on the Bay	Stephen Taber	Learn More Open in New Tab
September 24–28, 2024 Tuesday to Saturday	4 nights	Fall foliage!	Mary Day	Learn More Open in New Tab
September 24–28, 2024 Tuesday to Saturday	4 nights	Lighthouse cruise	Lewis R. French	Learn More Open in New Tab
September 24–28, 2024 Tuesday to Saturday	4 nights	Four-night adventure	Grace Bailey	Learn More Open in New Tab
September 25–29, 2024 Wednesday to Sunday	4 nights	Scenic Maine Photography cruise	J. & E. Riggin	Learn More Open in New Tab
September 25–29, 2024 Wednesday to Sunday	4 nights	Four-night cruise	Ladona	Learn More Open in New Tab
September 27–October 1, 2024 Friday to Tuesday	4 nights	Autumn on the Bay	Stephen Taber	Learn More Open in New Tab
September 28–October 1, 2024 Saturday to Tuesday	3 nights	Lobsters, sailing and music	Heritage	Learn More Open in New Tab
September 29–October 3, 2024 Sunday to Thursday	4 nights	Lighthouse and foliage cruise	Angelique	Learn More Open in New Tab

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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.

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