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 121 total 4 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
August 26–30, 2025 Tuesday to Saturday |
4 nights | $1580 | Camden Windjammer Festival | Grace Bailey | Learn More |
|
August 26–30, 2025 Tuesday to Saturday |
4 nights | $1350 | Camden Windjammer Festival | J. & E. Riggin | Learn More |
|
August 27–31, 2025 Wednesday to Sunday |
4 nights | $1358 | Camden Windjammer Festival | Stephen Taber | Learn More |
|
September 1–5, 2025 Monday to Friday |
4 nights | $1328 | Music w/Chicky Stoltz & Ragged Co. | Stephen Taber | Learn More |
|
September 2–6, 2025 Tuesday to Saturday |
4 nights | $1185 | Knit-a-long with Captain Becky | Lewis R. French | Learn More |
|
September 13–17, 2025 Saturday to Wednesday |
4 nights | $1185 | Four-night cruise | Lewis R. French | Learn More |
|
September 14–18, 2025 Sunday to Thursday |
4 nights | $1480 | Music & Sailing with Larksgrove | Grace Bailey | Learn More |
|
September 14–18, 2025 Sunday to Thursday |
4 nights | $1895 | 207 Creatives: Rug Hooking Retreat | J. & E. Riggin | Learn More |
|
September 14–18, 2025 Sunday to Thursday |
4 nights | $1290 | Just sail & relax | Mary Day | Learn More |
|
September 14–18, 2025 Sunday to Thursday |
4 nights | $1968 | Four nights, no set itinerary | Ladona | Learn More |
|
September 19–23, 2025 Friday to Tuesday |
4 nights | $1215 | Lighthouses & lobster cruise | J. & E. Riggin | Learn More |
|
September 19–23, 2025 Friday to Tuesday |
4 nights | $1968 | Autumn on the Bay | Ladona | Learn More |
|
September 21–25, 2025 Sunday to Thursday |
4 nights | $1198 | Autumn on the Bay | Stephen Taber | Learn More |
|
September 21–25, 2025 Sunday to Thursday |
4 nights | $1128 | Celtic Isles | American Eagle | Learn More |
|
September 22–26, 2025 Monday to Friday |
4 nights | $1055 | Four-night cruise | Lewis R. French | Learn More |
|
September 23–27, 2025 Tuesday to Saturday |
4 nights | $1425 | Sips & sailing with Luce Spirits | Grace Bailey | Learn More |
|
September 23–27, 2025 Tuesday to Saturday |
4 nights | $1290 | Fall foliage! | Mary Day | Learn More |
|
September 24–28, 2025 Wednesday to Sunday |
4 nights | $1315 | Sip & Sail: Craft cocktails of Maine | J. & E. Riggin | Learn More |
|
September 24–28, 2025 Wednesday to Sunday |
4 nights | $1968 | Autumn on the Bay | Ladona | Learn More |
|
September 26–30, 2025 Friday to Tuesday |
4 nights | $1198 | Autumn on the Bay | Stephen Taber | 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
