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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 14–17, 2026
Tuesday to Friday
3 nights $1340 Skygazing: New moon J. & E. Riggin
July 15–18, 2026
Wednesday to Saturday
3 nights $1025 Classic Windjamming adventure Lewis R. French
July 15–19, 2026
Wednesday to Sunday
4 nights $1398 4-night getaway Stephen Taber
July 17–20, 2026
Friday to Monday
3 nights $1530 Long weekend adventure Grace Bailey
July 17–20, 2026
Friday to Monday
3 nights $1187 Weekend getaway Mary Day
July 17–20, 2026
Friday to Monday
3 nights $1345 Kids & Family cruise J. & E. Riggin
July 19–23, 2026
Sunday to Thursday
4 nights $1400 Grandparents and Grandkids Angelique
July 19–25, 2026
Sunday to Saturday
6 nights $1700 Explore the Maine Coast Heritage
July 19–25, 2026
Sunday to Saturday
6 nights $1595 How far can we get from Camden? Lewis R. French
July 19–24, 2026
Sunday to Friday
5 nights Inquire
w/ Vessel
Full- reserved for private charter Ladona
July 20–25, 2026
Monday to Saturday
5 nights $1628 Camden Classic Cup Regatta Stephen Taber
July 21–25, 2026
Tuesday to Saturday
4 nights $1466 Bays & islands American Eagle
July 21–25, 2026
Tuesday to Saturday
4 nights $1705 Camden Classics Regatta Grace Bailey
July 21–25, 2026
Tuesday to Saturday
4 nights $1365 No itinerary; just relax & sail Mary Day
July 21–25, 2026
Tuesday to Saturday
4 nights $1460 Maine Lighthouses & Lobsters™ J. & E. Riggin
July 24–28, 2026
Friday to Tuesday
4 nights $1400 Grandparents and Grandkids Angelique
July 26–August 1, 2026
Sunday to Saturday
6 nights $1781 Unscripted adventure American Eagle
July 26–29, 2026
Sunday to Wednesday
3 nights $1530 Sailing & Maine humor with Gary Crocker Grace Bailey
July 26–30, 2026
Sunday to Thursday
4 nights $1300 Lobsters, sailing & music Heritage
July 26–29, 2026
Sunday to Wednesday
3 nights $1030 Classic Windjamming adventure Lewis R. French
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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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