So. You’re in a new city fresh on the dating scene, and you’re stuck: Um, where do I even begin to look for the most romantic places for a date in Boston? Don’t sweat Cassanova, we have a great list of suggestions for just about every kind of date. All you need to do is find someone to take with you.
For the go-getter who likes to laugh
Head to the North End for some authentic Italian cuisine and a comedy show at the award-winning Improv Asylum. Start your evening at Parla Restaurant, a hip restaurant with creative custom cocktails to suit any taste buds. Then sweep your date off to Prezza for a rustic Italian feel that blends the classics with some creative dishes, like anchovy-stuffed eggplant. In the mood for seafood? Put your name on the list at Neptune Oyster before you grab a drink since this favorite spot often has a long wait. Just don’t have too many cocktails and spoil your dinner. Then? It’s off to a laugh-fest. No matter who is on stage, it’s guaranteed to be a one-of-a-kind show, as is the nature of improv. We hope your date has a good sense of humor, too.
For the sports fans
It wouldn’t be Boston without a trip to see a Red Sox, Bruins, or Celtics game — that is, provided you’re both into sports. And there’s nothing like bonding over your favorite team’s win and we think this might be the best places for a first date in Boston or even for those who are just new to Boston. Pregame your outing with some killer BBQ at Sweetcheeks, where a good baseline of biscuits and honey butter will fuel you through the evening’s game time beers. Tip: during warmer months, opt for a spot outside to avoid the inevitably noisy atmosphere in the restaurant.
For the cute and romantic
You might think Kenmore Square is only for sports fans but think again. Surprise your date with classic or creative cocktails at The Hawthorne, where you can share in raising a curious eyebrow at each cocktail’s interesting combinations and flavor profiles. Then head across the hotel lobby (no driving required!) to Island Creek Oyster Bar, where you can lean in close for some of Boston’s best oysters. If the mood is right, sweep your date off to the Observatory for some stargazing — and maybe a smooch.
For the outdoorsy types
Daytime dates are fun, too — so lace up your shoes and head to the Blue Hills, just outside of downtown. With 7,000 acres of land, you’ll have plenty of room to wander hand-in-hand or try your luck on two wheels with a mountain biking adventure. Start your day with a hearty brunch at Newcomb Farms Restaurant in Milton just a few miles away from the park, fueling up on the classics like biscuits and gravy or a solid Eggs Benedict. In the warmer months you can pack your swimming gear for a post-hike dip, or if it’s winter in Boston, bring some hot cocoa for a post-ski or snowshoe warm-up while you plan your next adventure.
For the classic types
Boston has a LOT to offer those who want a more classic-style date, a la your favorite romance movie. Take a horse and carriage ride starting at Faneuil Hall and savor the sights of historic downtown. Reservations are generally only permitted for rides of an hour or longer, so you may need to just try your luck with a spontaneous visit to the hackney. Then, sweep your date off to Top Of the Hub (where you definitely made reservations in advance because it is considered one of the most romantic places for a date in Boston) for an excellent glass of wine and an amazing view from the top of the Prudential Center. You may want to spend the rest of your night there, enjoying the view and each other, but if you just can’t wrap up the date yet? Boston Commons is a short cab ride away, where you and your sweetheart can go skating on the Frog Pond in the winter.
For the gamers
Bar vibes, pub food, and video games? All the best things are in one place. Take your date to A4Cade on Mass Ave in Cambridge for a healthy competition to see who really is the best shot at skeeball. If you wear out your gaming skills, head over to the Cambridge Brewing Company to finish the evening with some award-winning brews from the conventional Belgian to the unconventional sours. You’ll be laughing and cozied up together in a booth before you know it.
Now that you know the most romantic places for a date in Boston, what are you waiting for?
