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 15–19, 2024 Sunday to Thursday |
4 nights | Just sail & relax | Mary Day | Learn More |
| September 15–19, 2024 Sunday to Thursday |
4 nights | Full-private charter | Ladona | Learn More |
| September 15–19, 2024 Sunday to Thursday |
4 nights | Four-night adventure hosted by Marc Evan Jackson | Grace Bailey | Learn More |
| September 15–19, 2024 Sunday to Thursday |
4 nights | Cool Days and Cozy Nights | American Eagle | Learn More |
| September 18–23, 2024 Wednesday to Monday |
5 nights | Rest & Restore Massage | Lewis R. French | Learn More |
| September 20–24, 2024 Friday to Tuesday |
4 nights | Maine Lighthouses and Lobsters | J. & E. Riggin | Learn More |
| September 20–23, 2024 Friday to Monday |
3 nights | Fall weekend getaway | Mary Day | Learn More |
| September 20–24, 2024 Friday to Tuesday |
4 nights | Four-night cruise | Ladona | Learn More |
| September 20–23, 2024 Friday to Monday |
3 nights | Three-night adventure hosted by Marc Evan Jackson | Grace Bailey | Learn More |
| September 20–24, 2024 Friday to Tuesday |
4 nights | Celtic among the Isles | American Eagle | Learn More |
| September 21–27, 2024 Saturday to Friday |
6 nights | Explore the Maine Coast | Heritage | Learn More |
| September 22–28, 2024 Sunday to Saturday |
6 nights | Six-night cruise | Angelique | Learn More |
| September 22–26, 2024 Sunday to Thursday |
4 nights | Autumn on the Bay | Stephen Taber | Learn More |
| September 24–28, 2024 Tuesday to Saturday |
4 nights | Fall foliage! | Mary Day | Learn More |
| September 24–28, 2024 Tuesday to Saturday |
4 nights | Lighthouse cruise | Lewis R. French | 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
