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 276 sailing adventures.
Dates | Length | Price /person |
Vessel | ||
---|---|---|---|---|---|
July 26–30, 2026 Sunday to Thursday |
4 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
July 26–August 1, 2026 Sunday to Saturday |
6 nights | $1550 | Lighthouse Cruise | Mary Day | Learn More |
July 26–August 1, 2026 Sunday to Saturday |
6 nights | $1730 | Music & Storytelling w/Geoff Kauffman | J. & E. Riggin | Learn More |
July 29–August 2, 2026 Wednesday to Sunday |
4 nights | $1450 | Yoga & wellness cruise | Angelique | Learn More |
July 29–August 1, 2026 Wednesday to Saturday |
3 nights | $1030 | Classic Windjamming adventure | Lewis R. French | Learn More |
July 29–August 1, 2026 Wednesday to Saturday |
3 nights | $1248 | 3-night getaway | Stephen Taber | 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 2–8, 2026 Sunday to Saturday |
6 nights | $1595 | Swan's Island Music Festival | Lewis R. French | Learn More |
August 2–8, 2026 Sunday to Saturday |
6 nights | $1898 | Captain's Choice | Stephen Taber | Learn More |
August 2–8, 2026 Sunday to Saturday |
6 nights | $1550 | Captain's favorite harbors | Mary Day | 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 3–8, 2026 Monday to Saturday |
5 nights | $1525 | Whales & seabirds cruise | Angelique | Learn More |
August 4–8, 2026 Tuesday to Saturday |
4 nights | $1705 | Four night adventure | Grace Bailey | Learn More |
August 5–8, 2026 Wednesday to Saturday |
3 nights | $1798 | 3-night sail | Ladona | Learn More |
August 6–9, 2026 Thursday to Sunday |
3 nights | $1245 | Perseid Meteor Showers | Heritage | Learn More |
August 6–10, 2026 Thursday to Monday |
4 nights | $1460 | Maine Lighthouses & Lobsters | J. & E. Riggin | Learn More |
August 7–10, 2026 Friday to Monday |
3 nights | $1308 | Main sails & Lobster tails | American Eagle | 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