Find My Trip
Use the “Find My Trip” tool to search for cruises by date. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page. Clicking “Learn more” will bring you to each Windjammer’s individual website where you can find cabin availability and all the details.
Prices start at $875 per person. Your cruise fare covers the entire experience: the sailing, all home-cooked meals, hors d’oeuvres, and desserts, and your private cabin aboard a historical schooner. Shore excursions—including the beloved island lobster bake—are included, with no hidden fees or extra charges along the way.
Maine resident? Learn more about our Maine resident discounts!
Hoping to sail in August? Visit our featured August sailings.
We found 127 total 4 night and 5 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
July 30–August 3, 2027 Friday to Tuesday |
4 nights | $1686 | Islands & Villages | American Eagle | Learn More |
|
August 1–5, 2027 Sunday to Thursday |
4 nights | $1550 | Grandparents and Grandkids | Angelique | Learn More |
|
August 1–5, 2027 Sunday to Thursday |
4 nights | $1725 | Perseid Meteor Showers | Heritage | Learn More |
|
August 1–5, 2027 Sunday to Thursday |
4 nights | $1645 | Sip & Sail: Wine pairing w/Kim Hamlin | J. & E. Riggin | Learn More |
|
August 3–7, 2027 Tuesday to Saturday |
4 nights |
Inquire w/ Vessel |
FULL - private charter | Stephen Taber | Learn More |
|
August 4–8, 2027 Wednesday to Sunday |
4 nights | $1686 | Bays & Islands | American Eagle | Learn More |
|
August 5–9, 2027 Thursday to Monday |
4 nights | $1570 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
August 6–10, 2027 Friday to Tuesday |
4 nights | $1725 | Perseid Meteor Showers | Heritage | Learn More |
|
August 9–14, 2027 Monday to Saturday |
5 nights | $1934 | Coastal Classics | American Eagle | Learn More |
|
August 10–14, 2027 Tuesday to Saturday |
4 nights | $1550 | Perseid Meteor Shower | Angelique | Learn More |
|
August 10–14, 2027 Tuesday to Saturday |
4 nights | $1605 | Perseids Meteor Shower | J. & E. Riggin | Learn More |
|
August 11–15, 2027 Wednesday to Sunday |
4 nights | $1525 | Lobsters, Sailing & Music | Heritage | Learn More |
|
August 15–19, 2027 Sunday to Thursday |
4 nights | $1550 | Windjammer & Watercolors | Angelique | Learn More |
|
August 15–19, 2027 Sunday to Thursday |
4 nights | $1570 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
August 15–19, 2027 Sunday to Thursday |
4 nights | $1705 | Four Night Adventure | Grace Bailey | Learn More |
|
August 16–20, 2027 Monday to Friday |
4 nights | $1450 | Sailing & Kayaking | Lewis R. French | Learn More |
|
August 16–21, 2027 Monday to Saturday |
5 nights | $1725 | Lighthouses & Shore Trips | Heritage | Learn More |
|
August 22–26, 2027 Sunday to Thursday |
4 nights | $1615 | Islands & Villages | American Eagle | Learn More |
|
August 22–26, 2027 Sunday to Thursday |
4 nights | $1438 | 4-night getaway | Stephen Taber | Learn More |
|
August 24–28, 2027 Tuesday to Saturday |
4 nights | $1650 | Farn-to-Table Barn Dinner | Angelique | 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
