Book My Trip
Use the “Book My Trip” box above to search for cruise dates. Cruises end in mid-October and begin again in May. You can also find each vessel’s schedule by visiting their fleet page.
207 sailing adventures found.
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| Dates | Length | Vessel | ||
|---|---|---|---|---|
| October 1–5, 2023 Sunday to Thursday |
4 nights | Foliage and Lighthouse Cruise | Angelique | Learn More Open in New Tab |
| October 1–5, 2023 Sunday to Thursday |
4 nights | Fall Colors in Full Swing | American Eagle | Learn More Open in New Tab |
| October 1–7, 2023 Sunday to Saturday |
6 nights | Downrig | Lewis R. French | Learn More Open in New Tab |
| October 1–4, 2023 Sunday to Wednesday |
3 nights | Fall Foliage | Grace Bailey | Learn More Open in New Tab |
| October 2–6, 2023 Monday to Friday |
4 nights | Sip & Sail: Cocktail Craft w/Lara Nixon | J. & E. Riggin | Learn More Open in New Tab |
| October 4–7, 2023 Wednesday to Saturday |
3 nights | Fall Colors | Ladona | Learn More Open in New Tab |
| October 5–9, 2023 Thursday to Monday |
4 nights | 4-Night Fall Colors Cruise | Stephen Taber | Learn More Open in New Tab |
| October 5–9, 2023 Thursday to Monday |
4 nights | Fall Foliage | Grace Bailey | Learn More Open in New Tab |
| October 6–9, 2023 Friday to Monday |
3 nights | Weekend Foliage Cruise | Angelique | Learn More Open in New Tab |
| October 6–9, 2023 Friday to Monday |
3 nights | Cool Days and Cozy Nights | American Eagle | Learn More Open in New Tab |
| October 7–11, 2023 Saturday to Wednesday |
4 nights | Fall Foliage Cruise | J. & E. Riggin | Learn More Open in New Tab |
| October 9–12, 2023 Monday to Thursday |
3 nights | Fall Colors | Ladona | Learn More Open in New Tab |
| October 10–14, 2023 Tuesday to Saturday |
4 nights | That's It For 2023! | American Eagle | Learn More Open in New Tab |
| October 10–13, 2023 Tuesday to Friday |
3 nights | 3-Night Fall Colors Cruise | Stephen Taber | Learn More Open in New Tab |
| October 13–16, 2023 Friday to Monday |
3 nights | Fall Colors | Ladona | Learn More Open in New Tab |
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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
