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 | ||
|---|---|---|---|---|
| June 3–7, 2024 Monday to Friday |
4 nights | Shakedown Sail! | American Eagle | Learn More |
| June 4–7, 2024 Tuesday to Friday |
3 nights | Lobsters, sailing and music | Heritage | Learn More |
| June 4–8, 2024 Tuesday to Saturday |
4 nights | Four-night adventure | Grace Bailey | Learn More |
| June 7–12, 2024 Friday to Wednesday |
5 nights | Windjammer Gam with music | Stephen Taber | Learn More |
| June 8–12, 2024 Saturday to Wednesday |
4 nights | Windjammer gam | Heritage | Learn More |
| June 8–13, 2024 Saturday to Thursday |
5 nights | Windjammer Gam | J. & E. Riggin | Learn More |
| June 8–11, 2024 Saturday to Tuesday |
3 nights | Just sail & relax | Mary Day | Learn More |
| June 8–13, 2024 Saturday to Thursday |
5 nights | Windjammer Gam | Lewis R. French | Learn More |
| June 8–12, 2024 Saturday to Wednesday |
4 nights | Windjammer Gam with music | Ladona | Learn More |
| June 8–13, 2024 Saturday to Thursday |
5 nights | Schooner Gam with live music | American Eagle | Learn More |
| June 9–15, 2024 Sunday to Saturday |
6 nights | Windjammer gam | Angelique | Learn More |
| June 9–14, 2024 Sunday to Friday |
5 nights | Windjammer Gam | Grace Bailey | Learn More |
| June 12–15, 2024 Wednesday to Saturday |
3 nights | Father's Day Getaway | Mary Day | Learn More |
| June 13–16, 2024 Thursday to Sunday |
3 nights | Lobsters, sailing and music | Heritage | Learn More |
| June 13–17, 2024 Thursday to Monday |
4 nights | Gourmet Gastropub | Stephen Taber | Learn More |
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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 SignupBrochures
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
