Find My Trip

Use the “Book 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.

216 sailing adventures found.

Page 1 of 15

Dates	Length		Vessel
May 22–26, 2025 Thursday to Monday	4 nights	Wine, dine and chocolate	Stephen Taber	Learn More
May 23–26, 2025 Friday to Monday	3 nights	FULL-private charter	Angelique	Learn More
May 23–27, 2025 Friday to Tuesday	4 nights	Music & dance cruise	J. & E. Riggin	Learn More
May 23–26, 2025 Friday to Monday	3 nights	Memorial Day Weekend	Lewis R. French	Learn More
May 27–30, 2025 Tuesday to Friday	3 nights	Lighthouses & lobster cruise	J. & E. Riggin	Learn More
May 27–30, 2025 Tuesday to Friday	3 nights	Available for private charter	Stephen Taber	Learn More
May 27–30, 2025 Tuesday to Friday	3 nights	Three-nights; no set itinerary	Ladona	Learn More
May 28–31, 2025 Wednesday to Saturday	3 nights	Wildlife cruise	Angelique	Learn More
May 28–June 1, 2025 Wednesday to Sunday	4 nights	Four-night cruise	Lewis R. French	Learn More
May 30–June 2, 2025 Friday to Monday	3 nights	Spring sailing!	American Eagle	Learn More
May 31–June 4, 2025 Saturday to Wednesday	4 nights	FULL-private charter	J. & E. Riggin	Learn More
May 31–June 4, 2025 Saturday to Wednesday	4 nights	Full - private charter	Stephen Taber	Learn More
May 31–June 4, 2025 Saturday to Wednesday	4 nights	Cooking with Melody and Anna	Ladona	Learn More
June 1–7, 2025 Sunday to Saturday	6 nights	Acadia National Park cruise	Angelique	Learn More
June 2–6, 2025 Monday to Friday	4 nights	Four-night cruise	Lewis R. French	Learn More

Page 1 of 15

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