Valentine’s Day For Couples: What To Do? | Portland Old Port

Valentine’s Day For Couples: What To Do?

It’s that time of year again, the day to celebrate love. We’re looking forward to seeing it splashed all over Portland thanks to the Valentine Bandit.

Now, it’s up to you and yours to find your own way to celebrate love and romance, but we’re here to help! Here are some Valentine’s Day happenings in and around Portland. Now, all you need is love!


Channel your inner Paris at Petite Jacqueline with their three- and five-course prix fixe menus ($55, $75). Enjoy courses ranging from sunchoke soup with white pepper, celery seed, and espelette to short rib with grilled rapini, celeriac alogot potato, and radish. Pretty sure we don’t have to say this but don’t forget the wine! PRO TIP: Order something old and red before you go and have it opened and waiting on the table so it can breathe. This also saves you from making an on-the-spot wine decision.

Really need to do Valentine’s Day right this year? Then Five Fifty-Five is a good call. They’ll be offering a four-course menu for $85, wine pairings optional. Check out the menu! That prosciutto-wrapped monkfish with Bang’s Island mussels, braised cabbage, local potatoes, and a leek emulsion looks pretty darn tasty, as does everything.

Taste your way through their five-course, family-style chef tasting OR order off the regular menu at Sur Lie. Reservations not required but encouraged.

Piccolo is a rustic Italian gem with only 20 seats, and everyone is precious. Husband-and-wife chef/owners Damian Sansonetti and Ilma Lopez will offer a five-course tasting menu for $75 per person, including house-made pasta, well-sourced ingredients, and the desserts…the desserts. Space is limited and there are two seatings to choose from, 5-6 p.m., 7:30-8:15 p.m. Sound interesting? Call…right…now.

For valentines, galentines, or guyentines,  hit up Valentine’s Dinner For Two! Expect Champagne and yummy desserts to top it all off will be available 4-10 p.m. at Little Tap House and you know it’s going to be SO good–earn those points! Who knows where it’ll lead?

Maine Table Restaurant will be featuring Valentine’s Day Dinner with delicious drinks, local beer, and a special Valentine’s Day menu made with fresh, local ingredients! This is worth leaving the Old Port for a bite. Call to make your reservations.

Mid-Week Oyster Social at Blyth & BurrowsYes, this event (5-9 p.m.) happens every single Wednesday, but that doesn’t make it any less special. Feast on $1 oysters and sip on all the $5 prosecco and $5 punch your heart desires.

Hit up the Loco Love Party at Margarita’s Mexican Restaurant with strawberry margaritas, “Sweetheart Baby Chimis,” games, prizes, and more!

Enjoy gourmet food, delicious drinks, and love songs to be performed by Double Entendre at Andy’s Old Port Pub, 7-10 p.m.


Share a love for Longfellow with your romantic partner? Then take a love-themed tour of the historic Wadsworth-Longfellow House here in Portland, Maine. In addition to leaving with a reproduction of a vintage valentine to the glass of Champagne or sparkling cider you’ll be handed when you walk in the door, this early evening affair will center on all things love, romance, and marriage in the Longfellow family. Along with your sparkling beverage enjoy some locally made Haven’s Candies, roses from Harmon’s & Bartons, and a singular literary experience. $50 per couple, $40 for Maine Historical Society members, available Feb. 11-14.

How about a Valentine’s Sweetheart Skate? Head to the Rink at Thompson’s Point from 6-9 p.m. and bring your Valentine for a romantic Valentine’s Day skate. They’re setting the mood right with music, lights, drinks, and buy one ticket, get your date in for free!

Heat things up with your valentine by enjoying a spicy salsa dance lesson and live dancing at The Pearl together! Live dancing follows the lessons with a live DJ from 9-midnight, $3 well drinks and $4 Coronas!


Vena’s Fizz House has been nailing specialty cocktails in the Old Port neighborhood since 2013 and has been a popular spot for upscale drinkers and a wide range of national media, as well. Start your romantic night off with a visit here, as Vena’s will be offering couples two of their perfectly made cocktails and a small plate. Then, definitely, think dessert…and make it happen! Vena’s also offers mocktails and non-alcoholic drinks. Family friendly!

If you’re planning a quiet dinner at home, visit Rosemont Market & Bakery for Valentine’s Sugar Cookie Decorating! the pastry team will be ready 4-6 p.m. to add icing to literally anything you’d like on your cookies (they don’t judge!).


Do you and yours live for Maine-made brews? Then Beer Hearts Chocolate at Allagash Brewing Company is for you. The world-famous brewery is about a 20-minute drive from downtown Portland, and is worth the drive, especially when beer and chocolate are involved. This beer pairing event will be held at the brewery and features the work of three local chocolatiers: La Crème Chocolat, Haven’s Candies, and Dean’s Sweets. Four chocolates will be paired with four Allagash offerings, including Coolship Red, Little Sal, Curieux, and St. Klippenstein. Need a “sober” moment? Visit the valentine-making station and do your worst in the photo booth. All proceeds benefit The American Heart Association.

Hone your tasting and pairing skills to match your wine with every meal! Pairings 101: Valentine’s Day Edition at Cellardoor Winery at the Point. This event puts the emphasis on learning about pairing complementary and contrasting flavors. Education in its’ best form: wine!

Nothing like a post-work, pre-date (or not) Valentine’s Day Beer Float Party at Rising Tide Brewing CompanyThe Gelato Fiasco and Rising Tide will have a selection of pairings of handmade gelato, fresh Rising Tide beer (or root beer for the underaged!).

Hop aboard the Maine Brew Bus BEer MINE Tour, which will include a stop at Black Dinah Chocolatiers factory in Westbrook for a chocolate and beer pairing!