Whether you’re on your first date or coming up on your 25th anniversary, you’re going to want to pull out all the stops to impress that special someone. With its graceful European-style architecture, swathes of green space, and world-class museums, Boston is the perfect stage for romance—provided you know where to go. Forget the tourist traps and focus on creating a curated itinerary that showcases the best dining and culture the city has to offer. Traveling by Uber spares you the hassle of public transportation and allows the two of you to enjoy each other’s company. If your significant other loves high culture, high society, or just a ball game and a couple of brews, any of these dates are guaranteed to sweep them off their feet.
The Culture Hound
Swing by the café at the Isabella Stewart Gardner Museum, which offers bistro fare in the gorgeously restored mansion of one of Boston’s most famous socialites and art collectors, before heading to the Institute of Contemporary Art, Boston on the wharf for cutting-edge works by contemporary artists such as Shepard Fairey. The setting, a feat of modern architecture encased in glass and steel, is almost as striking as its ever-changing exhibitions. Hop an Uber over to Papercuts J.P., an indie bookstore in Jamaica Plain, for a quick browsing session, then grab dinner at Genki Ya, a hip sushi spot in the theater district, before catching a show.
The Sports Fan
Of course, you’re going to a game at Fenway Park, the oldest stadium in Major League Baseball. Before the first pitch, grab a beer at Bleacher Bar, a recent addition tucked directly beneath the seats overlooking center field. Root for the home team, cheer when a batter hits one over the Green Monster, and belt out “Sweet Caroline” with all the other fans. Skip the overrated bratwursts at the stadium and grab some slicker charcuterie afterward at Bronwyn, a stylish German restaurant where chef Tim Wiechmann bakes up pretzels worthy of a Bavarian beer hall. Split the Königsteller (“king’s plate”), a heaping platter of crispy pork knuckles, house-made sausages, and sauerkraut for two.
The Glamour Set
For sheer sophistication, nothing tops high tea with Champagne at the Taj Boston. A live harpist sets the mood while you sip custom-blended teas and nibble on buttery scones slathered with clotted cream. Follow a decadent afternoon with an aperitif and a natural aphrodisiac at Neptune Oyster, a shoebox-size restaurant with the best bivalves in the North End. Nearly two dozen varieties, all impeccably fresh and shucked to order, are on the menu. From its contemporary French cuisine to its prestigious address, everything about L’Espalier screams class. With locally sourced produce from the chef’s own farm and showstopping, seasonal degustation menus, this is the place to dazzle even the most jaded gourmand. End your evening with a nightcap at Clink., at the site of the city’s former penitentiary.