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 | ||
|---|---|---|---|---|---|
|
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 |
|
July 10–19, 2026 Friday to Sunday |
9 nights | $2822 | Sail Boston! | American Eagle | Learn More |
|
July 10–14, 2026 Friday to Tuesday |
4 nights | $1225 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
July 10–14, 2026 Friday to Tuesday |
4 nights | $1398 | Weekend Escape | Stephen Taber | Learn More |
|
July 10–13, 2026 Friday to Monday |
3 nights | $1420 | Sip & sail: Craft Cocktails | J. & E. Riggin | Learn More |
|
July 12–16, 2026 Sunday to Thursday |
4 nights | $1705 | Four night adventure | Grace Bailey | Learn More |
|
July 12–18, 2026 Sunday to Saturday |
6 nights | $1700 | Explore the Maine Coast | Heritage | Learn More |
|
July 12–16, 2026 Sunday to Thursday |
4 nights | $1365 | No itinerary; just relax & sail | Mary Day | Learn More |
|
July 13–18, 2026 Monday to Saturday |
5 nights | $2828 | 5-night sail: new moon | 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
