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 | ||
|---|---|---|---|---|
| July 28–31, 2024 Sunday to Wednesday |
3 nights | Three-night getaway | Stephen Taber | Learn More |
| July 28–August 3, 2024 Sunday to Saturday |
6 nights | Tallship Sailing & Seamanship Course | Mary Day | Learn More |
| July 28–August 3, 2024 Sunday to Saturday |
6 nights | Six night cruise | Lewis R. French | Learn More |
| July 28–31, 2024 Sunday to Wednesday |
3 nights | Three-night adventure | Grace Bailey | Learn More |
| July 31–August 3, 2024 Wednesday to Saturday |
3 nights | Three-night getaway | Stephen Taber | Learn More |
| August 1–5, 2024 Thursday to Monday |
4 nights | Yoga and wellness cruise | Angelique | Learn More |
| August 1–6, 2024 Thursday to Tuesday |
5 nights | Live music cruise | J. & E. Riggin | Learn More |
| August 1–5, 2024 Thursday to Monday |
4 nights | Weekend escape | Ladona | Learn More |
| August 1–5, 2024 Thursday to Monday |
4 nights | Eggemoggin Reach Regatta | Grace Bailey | Learn More |
| August 2–5, 2024 Friday to Monday |
3 nights | Eggemoggin Reach Regatta | American Eagle | Learn More |
| August 3–7, 2024 Saturday to Wednesday |
4 nights | Perseid Meteor Showers | Heritage | Learn More |
| August 4–10, 2024 Sunday to Saturday |
6 nights | Captain's Choice | Stephen Taber | Learn More |
| August 4–10, 2024 Sunday to Saturday |
6 nights | Swan's Island Music Festival | Lewis R. French | Learn More |
| August 5–10, 2024 Monday to Saturday |
5 nights | Captain's favorite harbors cruise | Mary Day | Learn More |
| August 5–9, 2024 Monday to Friday |
4 nights | Full-private charter | Ladona | 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
