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 276 sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
August 9–13, 2026 Sunday to Thursday |
4 nights | $1350 | Perseid Meteor Showers | Angelique | Learn More |
|
August 9–15, 2026 Sunday to Saturday |
6 nights | $2265 | Six night adventure | Grace Bailey | Learn More |
|
August 9–12, 2026 Sunday to Wednesday |
3 nights | $1030 | Perseid Meteor Showers | Lewis R. French | Learn More |
|
August 9–15, 2026 Sunday to Saturday |
6 nights | $1898 | New Moon stargazing | Stephen Taber | Learn More |
|
August 9–16, 2026 Sunday to Sunday |
7 nights | $3438 | Ports Unknown: Secrets of Outer islands | Ladona | Learn More |
|
August 9–15, 2026 Sunday to Saturday |
6 nights | $1550 | Perseid Meteor Showers | Mary Day | Learn More |
|
August 10–14, 2026 Monday to Friday |
4 nights | $1300 | Lobsters, sailing & music | Heritage | Learn More |
|
August 11–15, 2026 Tuesday to Saturday |
4 nights | $1466 | Perseid Meteor Showers | American Eagle | Learn More |
|
August 11–15, 2026 Tuesday to Saturday |
4 nights | $1480 | Perseids Meteor showers | J. & E. Riggin | Learn More |
|
August 13–16, 2026 Thursday to Sunday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
August 14–18, 2026 Friday to Tuesday |
4 nights | $1350 | Weekend getaway | Angelique | Learn More |
|
August 15–19, 2026 Saturday to Wednesday |
4 nights | $1300 | Sail the Maine Coast w/Murder Mystery dinner! | Heritage | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1466 | Hiking & Island exploration | American Eagle | Learn More |
|
August 16–22, 2026 Sunday to Saturday |
6 nights | $2265 | Music & Sailing with Dennis Warner | Grace Bailey | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1568 | Local Culinary Heroes | Stephen Taber | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1365 | No itinerary; just relax & sail | Mary Day | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1460 | Maine Lighthouses & Lobsters | J. & E. Riggin | Learn More |
|
August 17–21, 2026 Monday to Friday |
4 nights | $1295 | Sailing & Kayaking | Lewis R. French | Learn More |
|
August 17–21, 2026 Monday to Friday |
4 nights | $2388 | 4-night sail | Ladona | Learn More |
|
August 19–23, 2026 Wednesday to Sunday |
4 nights | $1350 | Windjammer & Watercolors | Angelique | 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
