Find My Trip
Use the “Find 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.
We found 53 total 1 night, 2 night and 3 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
May 22–25, 2026 Friday to Monday |
3 nights |
Inquire w/ Vessel |
Booked for private charter | Angelique | Learn More |
|
May 22–25, 2026 Friday to Monday |
3 nights | $825 | Memorial Day weekend | Lewis R. French | Learn More |
|
May 26–29, 2026 Tuesday to Friday |
3 nights | $1155 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
May 27–30, 2026 Wednesday to Saturday |
3 nights | $900 | Wildlife cruise | Angelique | Learn More |
|
May 27–30, 2026 Wednesday to Saturday |
3 nights | $1248 | 3-night sail | Ladona | Learn More |
|
May 28–30, 2026 Thursday to Saturday |
2 nights |
Inquire w/ Vessel |
Available for private charter | Stephen Taber | Learn More |
|
May 29–June 1, 2026 Friday to Monday |
3 nights | $1048 | Spring sailing | American Eagle | Learn More |
|
June 2–5, 2026 Tuesday to Friday |
3 nights | $1100 | Lobsters, sailing & music | Heritage | Learn More |
|
June 3–6, 2026 Wednesday to Saturday |
3 nights | $1048 | Early summer sailing | American Eagle | Learn More |
|
June 11–14, 2026 Thursday to Sunday |
3 nights | $1100 | Lobsters, sailing & music | Heritage | Learn More |
|
June 12–15, 2026 Friday to Monday |
3 nights | $958 | Weekend getaway | Mary Day | Learn More |
|
June 14–17, 2026 Sunday to Wednesday |
3 nights | $1048 | Coastal Classics | American Eagle | Learn More |
|
June 17–20, 2026 Wednesday to Saturday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
June 19–22, 2026 Friday to Monday |
3 nights | $1240 | Long weekend adventure | Grace Bailey | Learn More |
|
June 20–21, 2026 Saturday to Sunday |
1 nights |
Inquire w/ Vessel |
Available for a one-night private charter! | J. & E. Riggin | Learn More |
|
June 21–24, 2026 Sunday to Wednesday |
3 nights | $1100 | Father's Day trip | Angelique | Learn More |
|
June 21–24, 2026 Sunday to Wednesday |
3 nights | $1498 | 3-night sail | Ladona | Learn More |
|
June 23–26, 2026 Tuesday to Friday |
3 nights | $1111 | Main sails & Lobster tails | American Eagle | Learn More |
|
July 5–8, 2026 Sunday to Wednesday |
3 nights | $1100 | Lobsters, sailing & music | Heritage | Learn More |
|
July 8–11, 2026 Wednesday to Saturday |
3 nights | $1100 | Lobsters, sailing & music | Heritage | Learn More |
Trying to book last minute?
You can find cabin availability on each vessel’s website. OR, use this form to let us know when you’re hoping to sail, how many people are in your party and what length trip you’re looking for. This form goes to all our member vessels at once. Any of the windjammers that can accommodate you will get back to you with cabin availability asap!
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
