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 119 total 4 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1550 | Four night adventure | Grace Bailey | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1998 | Autumn on the Bay | Ladona | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1290 | No itinerary; just relax & sail | Mary Day | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1345 | Maine Lighthouse & Lobsters | J. & E. Riggin | Learn More |
|
September 23–27, 2026 Wednesday to Sunday |
4 nights | $1055 | Knit along with Captain Becky | Lewis R. French | Learn More |
|
September 25–29, 2026 Friday to Tuesday |
4 nights | $1998 | Autumn on the Bay | Ladona | Learn More |
|
September 25–29, 2026 Friday to Tuesday |
4 nights | $1445 | Sip & Sail: Craft beers of Maine | J. & E. Riggin | Learn More |
|
September 26–30, 2026 Saturday to Wednesday |
4 nights | $1300 | Fall Foliage | Heritage | Learn More |
|
September 27–October 1, 2026 Sunday to Thursday |
4 nights | $1228 | Autumn on the Bay | Stephen Taber | Learn More |
|
September 28–October 2, 2026 Monday to Friday |
4 nights | $1055 | Fall foliage | Lewis R. French | Learn More |
|
September 29–October 3, 2026 Tuesday to Saturday |
4 nights | $1450 | Fall Foilage Four night adventure | Grace Bailey | Learn More |
|
September 29–October 3, 2026 Tuesday to Saturday |
4 nights | $1290 | Fall Foliage | Mary Day | Learn More |
|
September 30–October 4, 2026 Wednesday to Sunday |
4 nights | $1184 | Autumn on the Bay | American Eagle | Learn More |
|
September 30–October 4, 2026 Wednesday to Sunday |
4 nights | $1938 | Fall colors | Ladona | Learn More |
|
September 30–October 4, 2026 Wednesday to Sunday |
4 nights | $1365 | Fall Foliage cruise | J. & E. Riggin | Learn More |
|
October 1–5, 2026 Thursday to Monday |
4 nights | $1300 | Fall Foliage | Heritage | Learn More |
|
October 2–6, 2026 Friday to Tuesday |
4 nights | $1228 | Fall Colors | Stephen Taber | Learn More |
|
October 5–9, 2026 Monday to Friday |
4 nights | $1938 | Fall colors | Ladona | Learn More |
|
October 8–12, 2026 Thursday to Monday |
4 nights | $1198 | Fall Colors | 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
