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 | ||
---|---|---|---|---|---|
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 15–19, 2026 Wednesday to Sunday |
4 nights | $1398 | 4-night getaway | Stephen Taber | 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 19–23, 2026 Sunday to Thursday |
4 nights | $1400 | Grandparents and Grandkids | Angelique | Learn More |
July 19–25, 2026 Sunday to Saturday |
6 nights | $1700 | Explore the Maine Coast | Heritage | Learn More |
July 19–25, 2026 Sunday to Saturday |
6 nights | $1595 | How far can we get from Camden? | Lewis R. French | Learn More |
July 19–24, 2026 Sunday to Friday |
5 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
July 20–25, 2026 Monday to Saturday |
5 nights | $1628 | Camden Classic Cup Regatta | Stephen Taber | Learn More |
July 21–25, 2026 Tuesday to Saturday |
4 nights | $1466 | Bays & islands | American Eagle | Learn More |
July 21–25, 2026 Tuesday to Saturday |
4 nights | $1705 | Camden Classics Regatta | Grace Bailey | Learn More |
July 21–25, 2026 Tuesday to Saturday |
4 nights | $1365 | No itinerary; just relax & sail | Mary Day | Learn More |
July 21–25, 2026 Tuesday to Saturday |
4 nights | $1460 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
July 24–28, 2026 Friday to Tuesday |
4 nights | $1400 | Grandparents and Grandkids | Angelique | Learn More |
July 26–August 1, 2026 Sunday to Saturday |
6 nights | $1781 | Unscripted adventure | American Eagle | Learn More |
July 26–29, 2026 Sunday to Wednesday |
3 nights | $1530 | Sailing & Maine humor with Gary Crocker | Grace Bailey | Learn More |
July 26–30, 2026 Sunday to Thursday |
4 nights | $1300 | Lobsters, sailing & music | Heritage | Learn More |
July 26–29, 2026 Sunday to Wednesday |
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