The Perfect June Afternoon in Portland, Maine

You’ve just stepped off the Frances windjammer, your sea legs still a little wobbly, having had an unforgettable experience on a Wine Sail. A little windswept, lots of delicious wine in your belly, and new knowledge about how to taste wines like an expert fresh in your mind, and it’s still happy hour!!

These are all the reasons we adore our early afternoon Wine Sail, it leaves you your whole evening to curl up at a cozy table in one of Portland, Maine’s world-class restaurants, and relive the whole experience with even more incredible wine.

We’ve hand-selected a few of our favorite places to do so, where the food pairs perfectly with what you’ve been drinking, and where we can pass the baton onto one of the other fantastic Sommeliers in our foodie city.

Cheers! And hey, we might see you there!

Afternoon Wine Sails x Dinner

Friday, June 7

The Loire Valley Wine Sail | 3:15 - 5:15 PM

Isa Bistro: There’s just something about Loire wines and seared fish… Isa it is. Their menu changes seasonally but we can guarantee that Chef Isaul will be featuring gorgeous seafood fresh out of the water come summertime. Last we were in, Somm Suzie had an exquisite 2022 Domaine Hippolyte Reverdy, Sancerre Rosé on the list that went so beautifully with our entire meal. Ask her for this bottle, or another expert recommendation off her incredible wine list. A 5-minute cab ride – Reservations recommended.

Friday, June 14

Amber, Orange + Rosé Wine Sail | 3:15 - 5:15 PM

Eastern Promenade Food Trucks: Rosé all-day after the Wine Sail with a quick jaunt over to Eastern Promenade along a beautiful waterside walking path, where you’ll find a dozen or so excellent local food trucks, and a place to plop down on a picnic blanket and watch the evening go on with a panoramic view of Casco Bay’s calendar islands, historic forts, and picturesque lighthouses. 15 minute walk.

Saturday, June 15

South Africa Wine Sail | 3:15 - 5:15 PM

Asmara Restaurant: This tiny hidden gem can be found on a lane off Congress street. Inside the warm space with sweet spices in the air, communal, Eritrean cuisine is served with large pieces of flatbread called injera. These traditional dishes are rich with aromatic spices, slow-cooked meats and vegetarian options. The perfect pairing for the wines we serve on our South African Wine Sail! Go with a friend; these injera are massive yet won’t break the bank. 20 minute walk – Walk-ins welcome.

Friday, June 21

Italy Wine Sail | 3:15 - 5:15 PM

Solo Italiano: Dine al fresco at Solo Italiano – literally steps away from the Wine Sail dock. Though not facing the water, there are a select few tables in a semi-private nook that offers great people-watching. The service is A+, and you’ll still get the white tablecloth experience. A very special place to dine, in our honest opinion. When we go, we always order the Mandilli al Vero Pesto Genovese for the table with a bottle of vibrant, herbal, and minerally Pigato from Liguria, Chef Paolo’s neck of the woods. Less than 5 minute walk – Reservations recommended.

*Food photo credit:* *Via Vecchia Instagram*

Saturday, June 22

Italian Whites Wine Sail | 3:15 - 5:15 PM

Via Vecchia: It doesn’t get much more romantic than dipping under boughs of ivy to enter the 19th-century brick-laden beauty that is Via Vecchia. The interior is immaculate and glamorous, there isn’t a bad table in the house. Or make the iconic exterior your backdrop and sit outside on the leafy patio. Inquire with Susannah, the in-house Sommelier, for her favorite old-world wine pairing du jour. 5 minute walk – Reservations recommended.

*Food photo credits:* *Nicole Wolf* *for the* *Ugly Duckling*

Friday, June 28

Portugal + Spain Wine Sail | 3:15-5:15 PM

Ugly Duckling: Did all those visions of Portugal leave you drooling for Pastel de Natas? We have just the spot… Chef Ilma Lopez is a 2x James Beard Semi-Finalist for Best Pastry Chef in the country, and her West End spot, Ugly Duckling has Portuguese and Spanish inspired pastries and cocktails to continue your aperitivo hour. Keep the evening going at Chaval for European food and an incredible wine list. Insider tip: There’s a secret wine list with some aging beauties that Chef Sansonetti may just be ready to part with. 30 minute walk or 5 minute cab – Walk-in at Ugly Duckling, Reservations recommended for Chaval.

*Food photo credit:* *The Holy Trinity Greek Orthodox Instagram*

Sunday, June 30

Greece Wine Sail | 3:15-5:15 PM

Greek Fest: Head up the hill for the iconic, neighborhood block party that is The Holy Trinity Greek Orthodox Church’s Greek Fest! With live music, homemade Greek staples such as moussaka, gyro, spanakopita, baklava and greek coffee. Just remember to say thanks to the local Yiayia’s for sharing their family recipes. 20 minute walk or 5 minute cab – Bring cash

Stay tuned for July recommendations for more great wine sail + dinner pairings in Portland, Maine.

Kate PriorFebruary 27, 2024