Book My Trip
192 sailing adventures found.
Page 1 of 13
| Dates | Length | Vessel | ||
|---|---|---|---|---|
| June 9–14, 2023 Friday to Wednesday |
5 nights | Music & Schooner Gam w/Cattail Trio | Stephen Taber | Learn More Open in New Tab |
| June 10–15, 2023 Saturday to Thursday |
5 nights | Windjammer Fleet Raft-Up | American Eagle | Learn More Open in New Tab |
| June 10–14, 2023 Saturday to Wednesday |
4 nights | Schooner Gam - Gathering of the Fleet (Photo Tips w/Fred LeBlanc) | Heritage | Learn More Open in New Tab |
| June 10–14, 2023 Saturday to Wednesday |
4 nights | Live Music w/Cattail and Fleet Rendezvous | Ladona | Learn More Open in New Tab |
| June 10–15, 2023 Saturday to Thursday |
5 nights | The Schooner Gam | Lewis R. French | Learn More Open in New Tab |
| June 10–14, 2023 Saturday to Wednesday |
4 nights | Grace Bailey | Learn More Open in New Tab |
|
| June 11–17, 2023 Sunday to Saturday |
6 nights | Windjammer Gam | Angelique | Learn More Open in New Tab |
| June 11–15, 2023 Sunday to Thursday |
4 nights | No Itinerary; Just Sail & Relax | Mary Day | Learn More Open in New Tab |
| June 14–18, 2023 Wednesday to Sunday |
4 nights | Maine Knitting Cruises w/ Mim Bird | J. & E. Riggin | Learn More Open in New Tab |
| June 15–18, 2023 Thursday to Sunday |
3 nights | Lobsters, Sailing, and Music | Heritage | Learn More Open in New Tab |
| June 15–19, 2023 Thursday to Monday |
4 nights | Gourmet Gastropub Cruise w/Chef James Tranchemontagne | Stephen Taber | Learn More Open in New Tab |
| June 15–19, 2023 Thursday to Monday |
4 nights | Grace Bailey | Learn More Open in New Tab |
|
| June 16–19, 2023 Friday to Monday |
3 nights | Father's Day Weekend | American Eagle | Learn More Open in New Tab |
| June 16–19, 2023 Friday to Monday |
3 nights | Father’s Day Weekend | Lewis R. French | Learn More Open in New Tab |
| June 16–19, 2023 Friday to Monday |
3 nights | Father’s Day Weekend Getaway!/New Moon | Mary Day | Learn More Open in New Tab |
Page 1 of 13
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
