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 | ||
|---|---|---|---|---|---|
|
August 22–25, 2026 Saturday to Tuesday |
3 nights | $1798 | 3-night sail | Ladona | Learn More |
|
August 26–29, 2026 Wednesday to Saturday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
August 28–31, 2026 Friday to Monday |
3 nights | $1530 | Long weekend adventure | Grace Bailey | Learn More |
|
August 30–September 2, 2026 Sunday to Wednesday |
3 nights | $1308 | Main sails & Lobster tails | American Eagle | Learn More |
|
August 30–31, 2026 Sunday to Monday |
1 nights |
Inquire w/ Vessel |
Available for private charter | Stephen Taber | Learn More |
|
September 3–6, 2026 Thursday to Sunday |
3 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
|
September 9–12, 2026 Wednesday to Saturday |
3 nights | $1048 | Coastal Classics | American Eagle | Learn More |
|
September 19–22, 2026 Saturday to Tuesday |
3 nights | $995 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $1048 | Main sails & Lobster tails | American Eagle | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $1375 | Long weekend adventure | Grace Bailey | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $958 | Weekend getaway | Mary Day | Learn More |
|
October 5–8, 2026 Monday to Thursday |
3 nights | $1048 | One Last Turn around the Bay | American Eagle | Learn More |
|
October 10–13, 2026 Saturday to Tuesday |
3 nights | $1478 | Fall colors | Ladona | 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
