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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
July 26–August 1, 2026
Sunday to Saturday
6 nights $1550 Lighthouse Cruise Mary Day
July 26–August 1, 2026
Sunday to Saturday
6 nights $1730 Music & Storytelling w/Geoff Kauffman J. & E. Riggin
July 29–August 2, 2026
Wednesday to Sunday
4 nights $1450 Yoga & wellness cruise Angelique
July 29–August 1, 2026
Wednesday to Saturday
3 nights $1030 Classic Windjamming adventure Lewis R. French
July 29–August 1, 2026
Wednesday to Saturday
3 nights $1248 3-night getaway Stephen Taber
July 30–August 3, 2026
Thursday to Monday
4 nights $1705 Eggemoggin Reach Regatta Grace Bailey
July 31–August 4, 2026
Friday to Tuesday
4 nights $2388 Weekend escape Ladona
August 1–5, 2026
Saturday to Wednesday
4 nights $1445 Perseid Meteor Showers Heritage
August 2–6, 2026
Sunday to Thursday
4 nights $1466 Hiking & Island exploration American Eagle
August 2–8, 2026
Sunday to Saturday
6 nights $1595 Swan's Island Music Festival Lewis R. French
August 2–8, 2026
Sunday to Saturday
6 nights $1898 Captain's Choice Stephen Taber
August 2–8, 2026
Sunday to Saturday
6 nights $1550 Captain's favorite harbors Mary Day
August 2–6, 2026
Sunday to Thursday
4 nights $1535 Sip & Sail: Wine pairing w/Kim Hamlin J. & E. Riggin
August 3–8, 2026
Monday to Saturday
5 nights $1525 Whales & seabirds cruise Angelique
August 4–8, 2026
Tuesday to Saturday
4 nights $1705 Four night adventure Grace Bailey
August 5–8, 2026
Wednesday to Saturday
3 nights $1798 3-night sail Ladona
August 6–9, 2026
Thursday to Sunday
3 nights $1245 Perseid Meteor Showers Heritage
August 6–10, 2026
Thursday to Monday
4 nights $1460 Maine Lighthouses & Lobsters J. & E. Riggin
August 7–10, 2026
Friday to Monday
3 nights $1308 Main sails & Lobster tails American Eagle
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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!

Please note: We do our best to keep trip schedules as up-to-date as possible, however schedules are subject to change. We also do not track cabin availability on the Maine Windjammer Association website. For cabin availability or to confirm a specific sail date, please contact the vessel directly.

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 Signup

Brochures

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

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