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 2–8, 2024 Monday to Sunday |
6 nights | Six-night cruise | Ladona | Learn More |
| September 4–7, 2024 Wednesday to Saturday |
3 nights | Just sail & relax | Mary Day | Learn More |
| September 8–14, 2024 Sunday to Saturday |
6 nights | WoodenBoat Sail-In fleet gathering | Heritage | Learn More |
| September 8–14, 2024 Sunday to Saturday |
6 nights | Wooden Boat Sail-In fleet gathering | Angelique | Learn More |
| September 8–14, 2024 Sunday to Saturday |
6 nights | Wooden Boat Sail-In fleet gathering | J. & E. Riggin | Learn More |
| September 8–14, 2024 Sunday to Saturday |
6 nights | Wooden Boat Sail-In fleet gathering | Stephen Taber | Learn More |
| September 8–14, 2024 Sunday to Saturday |
6 nights | Wooden Boat Rendezvous | Mary Day | Learn More |
| September 8–13, 2024 Sunday to Friday |
5 nights | Wooden Boat Sail-In fleet gathering | Lewis R. French | Learn More |
| September 8–14, 2024 Sunday to Saturday |
6 nights | Wooden-Boat Sail-in | American Eagle | Learn More |
| September 9–14, 2024 Monday to Saturday |
5 nights | Wooden Boat Sail-in fleet gathering | Ladona | Learn More |
| September 14–17, 2024 Saturday to Tuesday |
3 nights | Three-night cruise | Lewis R. French | Learn More |
| September 15–18, 2024 Sunday to Wednesday |
3 nights | Lobsters, sailing and music | Heritage | Learn More |
| September 15–21, 2024 Sunday to Saturday |
6 nights | Six-night cruise | Angelique | Learn More |
| September 15–19, 2024 Sunday to Thursday |
4 nights | Sip & Sail cruise w/craft cocktails | J. & E. Riggin | Learn More |
| September 15–21, 2024 Sunday to Saturday |
6 nights | Wine, dine and cheese tasting | 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
