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 | ||
|---|---|---|---|---|---|
|
July 19–23, 2026 Sunday to Thursday |
4 nights | $1400 | Grandparents and Grandkids | Angelique | 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 26–30, 2026 Sunday to Thursday |
4 nights | $1300 | Lobsters, sailing & music | Heritage | Learn More |
|
July 26–30, 2026 Sunday to Thursday |
4 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
|
July 29–August 2, 2026 Wednesday to Sunday |
4 nights | $1450 | Yoga & wellness cruise | Angelique | Learn More |
|
July 30–August 3, 2026 Thursday to Monday |
4 nights | $1705 | Eggemoggin Reach Regatta | Grace Bailey | Learn More |
|
July 31–August 4, 2026 Friday to Tuesday |
4 nights | $2388 | Weekend escape | Ladona | Learn More |
|
August 1–5, 2026 Saturday to Wednesday |
4 nights | $1445 | Perseid Meteor Showers | Heritage | Learn More |
|
August 2–6, 2026 Sunday to Thursday |
4 nights | $1466 | Hiking & Island exploration | American Eagle | Learn More |
|
August 2–6, 2026 Sunday to Thursday |
4 nights | $1535 | Sip & Sail: Wine pairing w/Kim Hamlin | J. & E. Riggin | Learn More |
|
August 4–8, 2026 Tuesday to Saturday |
4 nights | $1705 | Four night adventure | Grace Bailey | Learn More |
|
August 6–10, 2026 Thursday to Monday |
4 nights | $1460 | Maine Lighthouses & Lobsters | J. & E. Riggin | Learn More |
|
August 9–13, 2026 Sunday to Thursday |
4 nights | $1350 | Perseid Meteor Showers | Angelique | Learn More |
|
August 10–14, 2026 Monday to Friday |
4 nights | $1300 | Lobsters, sailing & music | Heritage | Learn More |
|
August 11–15, 2026 Tuesday to Saturday |
4 nights | $1466 | Perseid Meteor Showers | American Eagle | Learn More |
|
August 11–15, 2026 Tuesday to Saturday |
4 nights | $1480 | Perseids Meteor showers | J. & E. Riggin | 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
