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 92 total 4 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
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 6–10, 2026 Saturday to Wednesday |
4 nights | $1300 | Windjammer Gam | Heritage | Learn More |
|
June 6–10, 2026 Saturday to Wednesday |
4 nights | $1248 | Music & Windjammer Gam | Stephen Taber | Learn More |
|
June 6–10, 2026 Saturday to Wednesday |
4 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
|
June 7–11, 2026 Sunday to Thursday |
4 nights | $1290 | No itinerary; just relax & sail | Mary Day | Learn More |
|
June 10–14, 2026 Wednesday to Sunday |
4 nights | $1320 | Knit, Crochet & Stitch w/Kim Hamlin | J. & E. Riggin | Learn More |
|
June 11–15, 2026 Thursday to Monday |
4 nights | $1248 | Gourmet Gastropub | Stephen Taber | Learn More |
|
June 11–15, 2026 Thursday to Monday |
4 nights | $1798 | Culinary Explorations with Fiore Olive Oils | Ladona | Learn More |
|
June 12–16, 2026 Friday to Tuesday |
4 nights | $1220 | Sailing & Hiking | Lewis R. French | Learn More |
|
June 14–18, 2026 Sunday to Thursday |
4 nights | $1450 | Four night adventure | Grace Bailey | Learn More |
|
June 15–19, 2026 Monday to Friday |
4 nights | $1248 | Summer Soltice & Live Music | Stephen Taber | Learn More |
|
June 15–19, 2026 Monday to Friday |
4 nights | $1295 | Scenic Maine photography w/Tracy Sheppard | J. & E. Riggin | Learn More |
|
June 16–20, 2026 Tuesday to Saturday |
4 nights | $1888 | Live music w/Jenn Schott | 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
