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 139 total 4 night and 5 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
September 26–30, 2025 Friday to Tuesday |
4 nights |
Inquire w/ Vessel |
Autumn on the Bay (booked for private charter) | American Eagle | Learn More |
|
September 27–October 1, 2025 Saturday to Wednesday |
4 nights | $1170 | Fall Foliage | Heritage | Learn More |
|
September 28–October 2, 2025 Sunday to Thursday |
4 nights | $1425 | Four Night Adventure | Grace Bailey | Learn More |
|
September 28–October 2, 2025 Sunday to Thursday |
4 nights | $1200 | Foliage and lighthouse cruise | Angelique | Learn More |
|
September 29–October 3, 2025 Monday to Friday |
4 nights | $1235 | FULL - private charter | J. & E. Riggin | Learn More |
|
September 29–October 3, 2025 Monday to Friday |
4 nights | $1908 | Fall colors | Ladona | Learn More |
|
October 1–5, 2025 Wednesday to Sunday |
4 nights | $1198 | Fall Colors | Stephen Taber | Learn More |
|
October 4–8, 2025 Saturday to Wednesday |
4 nights | $1908 | Fall colors | Ladona | Learn More |
|
October 4–8, 2025 Saturday to Wednesday |
4 nights | $1235 | Fall colors Getaway | J. & E. Riggin | Learn More |
|
May 21–25, 2026 Thursday to Monday |
4 nights | $998 | Wine, Dine & Chocolate | Stephen Taber | Learn More |
|
May 22–26, 2026 Friday to Tuesday |
4 nights | $1375 | Music & Dance w/The Gawler Family Band | J. & E. Riggin | Learn More |
|
May 27–31, 2026 Wednesday to Sunday |
4 nights | $1030 | Lighthouses! | Lewis R. French | Learn More |
|
May 30–June 3, 2026 Saturday to Wednesday |
4 nights | $1248 | 4-night getaway | Stephen Taber | Learn More |
|
May 30–June 3, 2026 Saturday to Wednesday |
4 nights | $1295 | Early Summer Getaway | J. & E. Riggin | Learn More |
|
May 31–June 4, 2026 Sunday to Thursday |
4 nights | $1798 | Cooking w/Chef Melody Wolfretz | Ladona | Learn More |
|
June 1–5, 2026 Monday to Friday |
4 nights | $1030 | Sailing & Hiking | Lewis R. French | Learn More |
|
June 2–6, 2026 Tuesday to Saturday |
4 nights | $1240 | Four night adventure | Grace Bailey | Learn More |
|
June 4–9, 2026 Thursday to Tuesday |
5 nights | $1480 | Windjammer Gam w/ Johnny & Brigid Reedy | J. & E. Riggin | Learn More |
|
June 6–10, 2026 Saturday to Wednesday |
4 nights | $1300 | Windjammer Gam | Heritage | Learn More |
|
June 6–11, 2026 Saturday to Thursday |
5 nights | $1255 | Windjammer Gam & Photo cruise | 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
