Romantic Things to Do on a Couples Trip to Boston
From low-key to over-the-top, these are the most fun and romantic things for couples to do in Boston.
Traveling is always better together—if no one took a picture of you tasting a perfect cocktail with a stunning view, did you even do it? So, let's dabble together in a bit of creativity, culture, and, of course, cocktails. Boston has limitless activities for couples, spanning from rooftop pools to handmade taco joints, arcades, nature walks, and ax throwing. For big romance vibes, there's always fine dining with panoramic city views and trendy restaurants. Here's a top-notch list of summery things to do for couples in Boston—from low-key picnic hangs to dramatic rooftop romance.
If you’d normally hit up a bar
Back Bay, Prices vary
Eschew the shadows and soak up the sun atop Boston's best sky-high locations, including The Colonnade Hotel and its swanky cabana rentals—Boston's only public-access rooftop pool. The pool is first come-first served, so swimming might require a little planning, but there’s a pretty extensive food and cocktail menu even if you don’t make it in the water.
Chinatown, $10 and up
Meet up for a few shareables at Shōjō's Chinatown location, and you're greeted with a contemporary aesthetic with an artsy overlay rooted in Asian culture. The creative cocktails and artwork will keep the convo flowing easily. The street art mural wall is incredible, the artwork is rotated regularly, and even the cocktail glasses are vibey. Grab an order of the fan-favorite Taiwanese Basil Popcorn Chicken and the mezcal-based One Thousand Deaths cocktail, featuring pea sprouts and Scorpion bitters.
South End, Free
Trade snooty, exclusive wine tasting for the approachable, inclusive, and oh-so-free tasting events at Urban Grape—a Black-owned and woman-owned sip shop. Their deep wine inventory features collections like Organic, Biodynamic, + Sustainable, Made in New England, and BIPOC Producers + Owners. Ease into date night by meandering their wine displays and choosing just the right bottle for the night's vibe. Better yet, attend one of Urban Grape's free wine or spirits tastings featuring brands like Mayflower Brewing. Also, be on the lookout for their Saturday after-brunch-themed tastings.
Back Bay, $22 and up
The door to Contessa takes you down a fairly dramatic hallway—to an elevator bound for the 17th floor. The fine dining restaurant overlooks the Back Bay and Boston Public Garden, so it's giving swoony romance energy. The menu is a love letter to Northern Italy, and the fresh-made pasta is sublime. Order the Wild Boar Ragu and put your trust in the sommelier to bring the perfect glass of wine. The overall ambiance is Old World Italy draped in glam. So, lean into it with a Seasonal Bellini—a perfectly balanced, refreshing sip of white peach and elderflower prosecco.
Cambridge, $5 and up
When you're not sure what cuisine would be the right call, Little Donkey is a go-to. The genius fever dream of James Beard Award Winning chef Ken Oringer, they serve global tapas—an unhinged array of international flavors and cuisines. Plus, the menu is labeled for gluten, vegan, and vegetarian needs, eliminating that potential stress from selecting a spot. Oysters deliver immediate romantic ambiance, so create a platter from their local selection. A casual $25 caviar sandwich? Yup, they've got that, but also $5 Mexican lagers.
If you like competition
Downtown, $5 cover
Boston date ideas aren't limited to what team's playing tonight, but if you're feeling playful, check out Versus. A $5 cover gives you full, no-token-needed access to nearly 40 arcade and video games. Snack on Jalapeno Stuffed Pretzels, burgers, flatbreads, and Zelda Fries between games of Space Invaders, Skee-ball, and Star Wars pinball. Score $6 PBRs or cozy up with your boo for a two-person cocktail (aka a multi-player drink) like the vodka-based Princess Peach. You can also increase the oops-our-fingers-touched moments by settling in with one of their board game options.
Somerville, $40 and up
Drinking and throwing axes—a modern-day tale of romance, of course. As far as dates go, it's absurdly fun. If you're new to ax-throwing, no worries. Your 90-minute booking begins with a quick lesson. They don't serve food, but they allow guests to bring in their own food, so grab some take-out or surprise your date with a low-key backpack-style charcuterie picnic. Either way, arrive early and grab a beer, wine, or cider from the bar. And yes, you can bring your food and drinks to your throwing area.
West End, Starting at $7
It's summer in Boston; of course, you'll max out on sports and lobster rolls. Not only is Banners known for its wonderfully absurd, mega-sized TV, but they also love warm weather menu specials and frequently feature one of the best lobster roll x beer specials in the city. If you're suave enough to plan a date night-game night overlap, there's no better way to dive in than a shareable order of Clothesline Smoked Bacon & Bourbon, which, luckily, is exactly what it sounds like. Later, work it off with a round of golf in the Topgolf Swing Suite lounge.
Dorchester, $10 and up
If you've got a partner down for a night of cheesy, spicy fries and roller skating, hold on tight and bust out your best moves at Chez-Vous. The beats are thumping, the wheels are rolling, and everyone's ditching the heat in style. The schedule changes with the seasons, but watch for date-friendly 18+ open skate hours throughout the week and events like ‘90s-themed shenanigans, complete with dance battles.
If you want to relax and feel cultured
Mission Hill, $5
MFABoston is a world-class art museum, with roughly 500,000 works in its collection, but it’s also an incredible bang for your buck on its $5 Community Celebration days. If you show up to buy a ticket in person after 5 pm on one of the dates from the special schedule, you’ll be treated to $5-minimum pay-what-you-wish tickets for you and your date, which is a pretty good price for experiencing timeless, priceless masterpieces.
Beacon Hill, Prices vary
Spend the day meandering Beacon Hill, then indulge in a farm-to-table picnic. The streets are cute, but you could also visit the Museum of African American History or Beacon Hill Books & Cafe. Close to both spots, you'll find Crane River Cheese Club—a chef-led specialty grocery store with oodles of farmed goods—ranging from local strawberries, cheese, meat, and bread. Grab a charcuterie box or some prepared foods and set up a picnic blanket on Boston Common. It's a one-and-done shop for gourmet al fresco dates.
Brookline, $20–$59
Making time for self-care in a relationship is its own love language and a really sweet way to reconnect with one another after a long week. Nomad Organic Spa offers $20 scalp treatments, $30 Chair Muscle Recovery Therapy, and Herbal Foot Reflexology, starting at $45 for 30 minutes. Schedule appointments for late morning so you can sleep in, and then, after your spa sesh, head over to Tatte Bakery for baked goods. Round out the date with a visit to Coolidge Corner Theatre to catch a new release or one of their many classic films or eclectic festivals.
Brookline, $10–$15
Spend a wholesome afternoon playing board games and eating tasty Prosciutto Fig sandwiches at Knight Moves Board Game Café. They're stocked with over 2,000 board games, and the game fee—$10 on weekdays and $15 over the weekend—is good from open to close. During your visit, you can play to your heart's content and come and go as you please. There are no cocktails, but the menu includes beautiful sandwiches like Apple Brie and a proper barista counter. Craving something in particular for your date? No worries. You can bring it for a $5 per person outside food fee.
Various locations
The secret to adorably memorable dates? Keep the Mass Audubon website handy. They offer plenty of free and under $25 programs and events at outdoorsy locations throughout the city and beyond. From a free Summer Bird Walk at Millennium Park to Queer BIPOC Nature Walk and even the beachy coastline vibes of Boston Shorebirds, their calendar is a seasonally rotating scroll of fresh air outings. If Boston nature dates are your jam, consider a $50 annual membership discounted to $25 for folks under 30.