October Fall Foliage Wine Sails 🍁
Celebrate October on the Water: Wine Sails in Portland, Maine
October in Maine is truly magical—the air is crisp, the leaves are bursting with brilliant reds, oranges, and golds, and Casco Bay glows in a whole new way. There’s no better way to experience it than aboard the immaculate 74-foot Frances for one of our October Fall Foliage Wine Sails.
Each Wine Sail features five sommelier-curated wines, carefully selected to transport you to vineyards in Italy, France, Spain, Oregon, California, and beyond. As you sip and learn, you’ll drift past historic lighthouses, rugged islands, and Portland’s working waterfront, all while soaking in the stunning fall foliage.
October is one of our favorite times to sail—cool, refreshing air, cozy sweaters, and sunsets that make every moment feel magical. Whether you’re joining for a regional wine exploration or a specialty sail, each experience blends wine education, relaxation, and unforgettable Maine beauty.
October Wine Sails
Ticket availability as of 10/09 (waitlists are Available for all sold-out events. You’ll be instantly notified if tickets become available.)
Thu, Oct 3, Wine & Oysters, 4:45–6:45 PM (sold out)
Thu, Oct 3, Italian Reds, 1:30–3:30 PM (sold out)
Fri, Oct 4, Autumn Whites, 1:30–3:30 PM (sold out)
Fri, Oct 4, Piedmont, 4:45–6:45 PM (sold out)
Sat, Oct 5, Chef Sansonetti of Chaval, 4:45–6:45 PM (sold out)
Sat, Oct 5, Napa & Sonoma, 1:30–3:30 PM (sold out)
Thu, Oct 10, Chef Sansonetti of Chaval, 4:45–6:45 PM (sold out)
Thu, Oct 10, Europe, 1:30–3:30 PM sold out)
Fri, Oct 11, Italy, 1:30–3:30 PM (sold out)
Fri, Oct 11, French Reds, 4:45–6:45 PM (sold out)
Sat, Oct 12, The Mediterranean, 1:30–3:30 PM (sold out)
Sat, Oct 12, Wine & Oysters, 4:45–6:45 PM (sold out)
Thu, Oct 17, France, 1:30–3:30 PM (sold out)
Fri, Oct 18, Shef Mimi of Bites & Such, 4:45–6:45 PM (sold out)
Sat, Oct 19, Sicily, 1:30–3:30 PM (sold out)
Seats are limited and sell out quickly—don’t miss your chance to enjoy fall in Portland from the water with a glass in hand. 🍁 Our October Wine Sails are the perfect way to celebrate the season, sip amazing wines, and make unforgettable memories.
