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 244 sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
June 23–27, 2026 Tuesday to Saturday |
4 nights | $1450 | Four night adventure | Grace Bailey | Learn More |
|
June 24–28, 2026 Wednesday to Sunday |
4 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
|
June 25–July 5, 2026 Thursday to Sunday |
10 nights | $3000 | America's 250th in NYC! Camden to NYC | Angelique | Learn More |
|
June 27–July 4, 2026 Saturday to Saturday |
7 nights | $2268 | The Great Schooner Race | Stephen Taber | Learn More |
|
June 28–July 9, 2026 Sunday to Thursday |
11 nights | $3218 | America's 250th in NYC! | American Eagle | Learn More |
|
June 28–July 4, 2026 Sunday to Saturday |
6 nights | $2265 | The Great Schooner Race | Grace Bailey | Learn More |
|
June 28–July 4, 2026 Sunday to Saturday |
6 nights | $1700 | Great Schooner Race | Heritage | Learn More |
|
June 28–July 4, 2026 Sunday to Saturday |
6 nights | $1550 | Great Schooner Race | Mary Day | Learn More |
|
June 28–July 4, 2026 Sunday to Saturday |
6 nights | $1705 | Great Schooner Race | J. & E. Riggin | Learn More |
|
June 29–July 4, 2026 Monday to Saturday |
5 nights | $1420 | Great Schooner Race | Lewis R. French | Learn More |
|
June 29–July 4, 2026 Monday to Saturday |
5 nights | $2588 | Great Schooner Race | Ladona | Learn More |
|
July 5–11, 2026 Sunday to Saturday |
6 nights | $2265 | Six night adventure | Grace Bailey | Learn More |
|
July 5–8, 2026 Sunday to Wednesday |
3 nights | $1100 | Lobsters, sailing & music | Heritage | Learn More |
|
July 5–9, 2026 Sunday to Thursday |
4 nights | $1295 | Sailing & Kayaking | Lewis R. French | Learn More |
|
July 5–9, 2026 Sunday to Thursday |
4 nights | $1398 | 4-night getaway | Stephen Taber | Learn More |
|
July 5–12, 2026 Sunday to Sunday |
7 nights | $3438 | Ports Unknown: Secrets of Mount Desert Island | Ladona | Learn More |
|
July 5–11, 2026 Sunday to Saturday |
6 nights | $1550 | No Smoking cruise | Mary Day | Learn More |
|
July 5–9, 2026 Sunday to Thursday |
4 nights | $1460 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
July 6–16, 2026 Monday to Thursday |
10 nights | $3000 | Sail Boston! NY to Camden via Boston | Angelique | 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
