The Wine Wise Guide for a Perfect Summer Day in Portland, Maine
Looking for the perfect summer day to share with your family and friends? We have all the guidance you need right here to set your course for the best and most memorable afternoon-into-evening experiences you can imagine in Portland, Maine, as we bring you from wine and sailing on the water to the dining rooms of the best restaurants.
Imagine for just one minute that it’s summer. You’re in beautiful coastal Portland, Maine. It’s sunny, warm, and blue-skyed. And plenty of ocean breeze to carry a sail across Casco Bay. You make your way to the oceanfront and board the immaculate Tall Ship, Frances. Just before you can’t believe the day will get any better, you’re handed a nice wine glass and hear the distinct squeak of a corkscrew making its way into the first bottle of an amazing wine. It has been hand chosen by a sommelier to be a benchmark example of the wine topic she’s going to cover, with four others to follow. You are on board a Wine Wise afternoon wine sail. And you are about to have a highlight event of your Summer.
Portland is notably one of the best cities for restaurants in the country. In 2018 Bon Appétit named Portland its Restaurant City of the Year. Since 2018 there have been over 40 James Beard nominations in a stunning range of categories—most residing with Portland chefs, restaurants, and hospitality superstars.
The best compliment to an afternoon wine sail is pairing it with dinner afterward at one of the abundant and culinarily diverse restaurants that Portland has to offer. Once back at the dock, it’s the perfect time for dinner—and about a 5-minute walk to where many fine restaurants are, but don’t limit yourself. The East and West Ends of Portland are also home to some of the best restaurants in the city and a quick and easy Uber ride from the pier.
This is a perfect Portland afternoon-into-evening experience. These celebrated Wine Sails are praised just as much by locals as by travelers all over the country, and what better way to extend the experience than dinner at an acclaimed restaurant?
The Wine Sails sell out ridiculously fast and way ahead of the Summer season! If you don’t want to miss one of these incredible tastings on the water, check out the June 9 - October 9 schedule and reserve right away. The same goes for a reservation at any restaurant in Portland. June is the start of the high season on the coast of Maine, and restaurant reservations can be as scarce as a seat on a Wine Sail, so we recommend planning way ahead and making your reservations for both!
Afternoon Wine Sails + Dinner pairings
Friday, June 23
Delicious Whites Wine Sail | 3:15 - 5:15 PM
Dinner at Helm | A short walk from the Maine State Pier, Helm. Feast on their raw oyster bar and a seasonal menu packed with locally-sourced, fine seafood, produce, and meats.
Friday, June 30
Pinot Noir Wine Sail | 3:15 - 5:15 PM
Dinner at Izakaya Minato | Here at Wine Wise, we love pairing cool-climate pinot noir with Minato’s savory Japanese food. Experience traditional izakaya dining in Portland’s East End. Taste their seasonal blend of sashimi, dashi broth dishes, grilled fish, and Japanese fried chicken. Let the chef select your meal for you by ordering omakase.
Friday, July 14
Portugal + Spain Wine Sail | 3:15-5:15 PM
Dinner at Chaval | Dine at one of the West End’s neighborhood gems with two of the city’s most acclaimed chefs. Experience local ingredients, amazing hospitality, and the Spanish & French seasonal cuisine of Chaval.
Saturday, July 22
Mediterranean Wine Sail | 3:15 - 5:15 PM
Dinner at EVO Kitchen + Bar | Fresh, flavorful seafood, vegetables, and meats at this stylish bistro for creative riffs on classic Mediterranean cuisine with a focus on local ingredients.
Friday, July 28
South African Wine Sail | 3:15 - 5:15 PM
Dinner at Asmara | Communal style cuisine served with large pieces of flatbread called injera. Traditional dishes are rich with aromatic spices. The perfect pairing for the wines we serve on our South African Wine Sail!
Sunday, August 13
Italian Wine Sail | 3:00 - 5:00 PM
Dinner at Via Vecchia | A small plates Italian-inspired restaurant. Located in the heart of the Old Port in an iconic brick and ivy-covered building overlooking cobblestone streets.
Sunday, September 3
French Wine Sail | 1:30 - 3:30 PM
Dinner at Wayside Tavern | A cozy, West End neighborhood restaurant located next to the Francis Hotel. Wayside Tavern offers Italian-inspired cuisine with a worldly wine list.
Stay tuned for Part II with our recommendations on more great Portland restaurants to dine at late-night, after our Sunset Wine Sails.
