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 | ||
|---|---|---|---|---|---|
|
July 10–13, 2026 Friday to Monday |
3 nights | $1420 | Sip & sail: Craft Cocktails | J. & E. Riggin | Learn More |
|
July 14–17, 2026 Tuesday to Friday |
3 nights | $1340 | Skygazing: New moon | J. & E. Riggin | Learn More |
|
July 15–18, 2026 Wednesday to Saturday |
3 nights | $1025 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1530 | Long weekend adventure | Grace Bailey | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1187 | Weekend getaway | Mary Day | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1345 | Kids & Family cruise | J. & E. Riggin | Learn More |
|
July 26–29, 2026 Sunday to Wednesday |
3 nights | $1530 | Sailing & Maine humor with Gary Crocker | Grace Bailey | Learn More |
|
July 26–29, 2026 Sunday to Wednesday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
July 29–August 1, 2026 Wednesday to Saturday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
July 29–August 1, 2026 Wednesday to Saturday |
3 nights | $1248 | 3-night getaway | Stephen Taber | Learn More |
|
August 5–8, 2026 Wednesday to Saturday |
3 nights | $1798 | 3-night sail | Ladona | Learn More |
|
August 6–9, 2026 Thursday to Sunday |
3 nights | $1245 | Perseid Meteor Showers | Heritage | Learn More |
|
August 7–10, 2026 Friday to Monday |
3 nights | $1308 | Main sails & Lobster tails | American Eagle | Learn More |
|
August 9–12, 2026 Sunday to Wednesday |
3 nights | $1030 | Perseid Meteor Showers | Lewis R. French | Learn More |
|
August 13–16, 2026 Thursday to Sunday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
August 20–23, 2026 Thursday to Sunday |
3 nights |
Inquire w/ Vessel |
3-day sail | J. & E. Riggin | Learn More |
|
August 21–24, 2026 Friday to Monday |
3 nights | $1308 | Coastal Classics | American Eagle | Learn More |
|
August 21–24, 2026 Friday to Monday |
3 nights | $1248 | Weekend Getaway | Stephen Taber | Learn More |
|
August 21–24, 2026 Friday to Monday |
3 nights | $1187 | Weekend getaway | Mary Day | Learn More |
|
August 22–25, 2026 Saturday to Tuesday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | 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
