Boston Valentine: 8 Great Places for Dates and Romance

How to warm the cockles of your heart and dial up the romance of your Boston rendezvous.

February brings cold and snow to Boston: brown-slushed streets, wet socks and chapped lips. With nothing but an April thaw to look forward to, the day’s frozen sidewalks and concrete skies blur into a mass of grey, but that doesn’t mean there isn’t light to be found, even if the rays of sunshine tend to be metaphorical. Although the second month of the calendar sits at the cold core of a Boston winter, February 14 is always St. Valentine’s Day, and fluttering hearts beat warmth across the city. If you need a little something to shake off the cold and heat up the romance this year, here’s a selection of thoroughly Bostonian, classically romantic dates to try out. All of them are guaranteed to add a splash of Technicolor to your enjoyment of the city, even while a blizzard cranks up the big freeze.

B&G Oysters


The fast track to amorous fun can be found this February in a little aphrodisiac: oysters. So put them on the menu for the night and head to the best place in town for bivalves: B&G Oysters. With a classic menu of expertly prepared New England seafood essentials, this South End restaurant has the feel of a beloved neighborhood hangout. The freshness of their fare is palpable on the tongue, and that shines best in their oyster selection. Light the candles, order a dozen or so, and get slurping.


There are few restaurants in Boston that are more of an event to visit than Top of the Hub. Located at the highest point of the city, its floor to ceiling and 360 degree views allow you to see Boston in a way you never have before. By night, the view is truly spectacular. It’s not just the sights that make Top of the Hub stand out, however, as the food and the drinks, the service and the atmosphere, will have you and your date feeling like high rollers. Try not to let your date notice that you’re eyes are fixed over their shoulder out the window and not at them.

Isabella Stewart Gardner Museum


Boston’s Fenway neighborhood hides one of the jewels of the city, and it’s not just Fenway Park. Instead of taking a stroll down Jersey Street, follow Park Drive to the Isabella Stewart Gardner Museum. Lifelong art collector Isabella Stewart Gardner filled this museum, designed to emulate a Venetian palace, with great works and opened it to the public. The ISG is the perfect place to spend a day strolling courtyards and admiring Rembrandts and Titians with a lover on your arm.


For some it’s all about the anticipation, and if you’re looking for an evening of perfect physical tension, why not do it under the guise of intellectual intrigue? On February 14-16, join Watson Adventures at 6:30 pm as they take to the Museum of Fine Arts for a guided, Valentine’s Day themed scavenger hunt. Love may not always be in the air of the paintings you track down, but everybody’s favorite body parts will be, as you’ll be following riddles, prompts and clues to try and track down the MFA’s finest selection of nudes in art.

Acorn Street, Beacon Hill


Boston’s most romantic neighborhood is Beacon Hill. With its brick facades and cobbled alleyways, it’s an enclave in the city that feels lost to time. While the sun is up, peruse the quiet, unassuming stores along Charles Street. When the dark comes, descend with the sun into the cave of a restaurant called The Hungry I. With its tall, wax-dripping candles and its low-slung ceiling, it’s an atmosphere sure to draw you closer to whoever sits across from you. When the meal is over, walk the maze of streets up and down the hill, lit by the warm glow of gas-fueled lamps.


The North End has the charm of Beacon Hill, though the flavor is distinctly different. There are hidden romantic hideouts and five-course gourmet meals to be had, but the best place to take a date in the North End is the original Regina Pizzeria. Squeeze into one of their worn wooden booths, order a pie and a pitcher of beer and let yourself sink into the scenery of this Boston classic. Afterwards take a walk through the endless streets and alleyways of the North End until you stumble across Bova’s Bakery. Order a cannoli, and work your way over to the park behind Old North Church. Smooches will be had, it’s a sure bet.


Cambridge is the land of the boho and the beatnik. Platform shoes and perfecto jackets are par for the course, and oddball restaurants, music venues and leftfield art installations can be found aplenty. While away the day at the Garment District, a trove of used, vintage and offbeat clothes, shoes and accessories. With airplanes hung from the ceiling and cars parked on the walls, this is a warehouse of weird where you’ll love to get lost for hours.

Isabella Stewart Gardner Museum