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 | ||
|---|---|---|---|---|
| August 6–10, 2024 Tuesday to Saturday |
4 nights | Watercolors cruise | Angelique | Learn More |
| August 6–9, 2024 Tuesday to Friday |
3 nights | Three-night adventure | Grace Bailey | Learn More |
| August 6–10, 2024 Tuesday to Saturday |
4 nights | Swan's Island Music Festival | American Eagle | Learn More |
| August 7–10, 2024 Wednesday to Saturday |
3 nights | Maine Lighthouses and Lobsters | J. & E. Riggin | Learn More |
| August 8–11, 2024 Thursday to Sunday |
3 nights | Perseid Meteor Showers | Heritage | Learn More |
| August 10–14, 2024 Saturday to Wednesday |
4 nights | Full-private charter | Ladona | Learn More |
| August 10–17, 2024 Saturday to Saturday |
7 nights | The Great Seven-Night Adventure | Grace Bailey | Learn More |
| August 11–16, 2024 Sunday to Friday |
5 nights | Perseids meteor shower | Angelique | Learn More |
| August 11–15, 2024 Sunday to Thursday |
4 nights | Perseids Meteor Shower | J. & E. Riggin | Learn More |
| August 11–17, 2024 Sunday to Saturday |
6 nights | Off the grid: Pen Bay's Hidden Gems | Stephen Taber | Learn More |
| August 11–17, 2024 Sunday to Saturday |
6 nights | Perseid Meteor Showers | Mary Day | Learn More |
| August 11–15, 2024 Sunday to Thursday |
4 nights | Four-night cruise | Lewis R. French | Learn More |
| August 11–17, 2024 Sunday to Saturday |
6 nights | Unscripted Adventure | American Eagle | Learn More |
| August 13–18, 2024 Tuesday to Sunday |
5 nights | Explore the Maine Coast | Heritage | Learn More |
| August 15–19, 2024 Thursday to Monday |
4 nights | Sip & Sail cruise w/craft beers | J. & E. Riggin | 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
