Wine Sail Gift Card Packages: The ultimate gift for everyone who deserves an unforgettable experience.

Wine & Oyster Sail Gift Card Packages: delicious wines, frech shucked Maine oysters, and sailing on the coast of Portland, Maine.

Gift Cards for a Specific Dollar Amount: can be applied to anything we offer, including Wine Sails in Portland, Maine, Fine Wine Cruises in Fort Lauderdale, Wine Wise Trips, & more.

Wine Sails | Enjoy fantastic wines, guided by our Sommelier, as you sail the stunning Portland coast aboard the immaculate tall ship Frances. Tickets are going quickly for the 2026 season!

Chef Series Wine & Food Sails | Our most exclusive offering indulges you in five sommelier-curated wines, each expertly paired with courses by some of Portland’s top chefs… all while sailing.

Wine & Oyster Sails | Savor the freshest Maine oysters—500 shucked to perfection—and five incredible wines. Experience the best in wine, oysters, and sailing along Maine’s stunning coast.

Fine Wine Cruises | Savor five Sommelier-curated fine wines alongside artisanal cheeses, cured meats, fresh fruit, nuts, and delicious accompaniments while cruising Fort Lauderdale's stunning Intracoastal Waterway.

Fine Wine & Maine Oyster Cruises | Indulge in five Sommelier-curated fine wines and 500 fresh Maine oysters, flown in overnight and expertly shucked aboard Sea Rocket while cruising Fort Lauderdale's Intracoastal Waterway.

Fine Wine & Maine Lobster Cruises | Indulge in the sweet, succulent flavors of fresh Maine lobster, beautifully prepared and served alongside a thoughtfully curated selection of fine wines for a truly delicious experience.

Barolo, Barbaresco & Lake Garda | Nov 1-11, 2026 (sold out)

Tuscany & Cinque Terre | May 2 - 12, 2027

JUST ADDED ✈️ Sicily | May 13 - 20, 2027