Last Chance Fall Sailing in 2026
Didn’t make it out sailing this summer? Fall’s open. Join us this fall as coast comes alive with color, the wind turns brisk, and the sailing’s at its best. Come haul a line, feel the boat heel, and get outside before winter closes the season.
We’ve compiled a list of last minute availability.
Aboard Schooner Mary Day
Sept 20–24, (Sun to Thurs) | $1450
No itinerary, Just relax and sail!
Sept 25–28 (Fri to Mon) | $1360
Weekend getaway!
Sept 29–Oct 3 (Tues to Sat) | $1450
Last sail for 2026
Aboard Schooner Grace Bailey
Sept 20–24 (Sun to Thurs) | $1550
Folk and Americana performer Caroline Cotter joins the trip to provide lamplit acoustic sets in the evenings.
Sept 25–28 (Fri to Mon) | $1375
Weekend getaway!
Sept 29–Oct 3 (Tues to Sat) | $1450
Fall foliage to end the season.
Aboard Schooner Heritage
Sept 26–30 (Sat to Wed) | $1300
Four-nights along the coast
Oct 1–5 (Thurs to Mon) | $1300
Four-nights along the coast
Aboard Schooner American Eagle
Sept 20–24 (Sun to Thurs) | $1302
Folk music duo Drank the Gold joins the cruise for evenings of music
Main Sails & Lobster Tails
Oct 5–Oct 8 (Mon to Thurs) | $1143
Folk/Americana musician Reese Fulmer joins the cruises
Aboard Schooner Stephen Taber
Sept 27–Oct 1 (Sun to Thurs) | $1228
Autumn on the Bay–sailing at its best
Fall colors–sailing at its best
Aboard Schooner Ladona
Sept 20–24 (Sun to Thurs) | $1998
Autumn on the Bay–sailing at its best
Aboard Schooner J. & E. Riggin
Sept 25–29 (Fri to Tues) | $1442
Maine Sip & Sail: Craft Beers
Sept 30–Oct 4 (Wed to Sun) | $1365
Fall foliage trip!
Category: Uncategorized
