Boston
Proper. 🏛️
Boston is walkable, historic, and undeniably romantic. We've filtered out the tourist traps to find the spots where the gas lamps still flicker and the oysters are always fresh.
Acorn Street
The Photo Op
"It is arguably the most photographed street in America. Original river stone cobbles, red brick row houses, and gas lamps. Walking down it feels like stepping into a 19th-century novel."
Beacon Hill.
This is "Old Boston." The streets are narrow, steep, and lined with ivy. It’s quiet, expensive, and incredibly intimate.
Bin 26 Enoteca
A cozy, dimly lit wine bar on Charles Street. It’s sophisticated without being stuffy. Perfect for a second date.
The Cannoli Wars. 🇮🇹
Hanover Street is chaos, but the side streets are magic. The air smells of garlic, basil, and espresso. The ultimate date debate: Mike's vs. Modern.
The "Modern" Choice
Locals usually prefer Modern Pastry. The shells are filled to order, so they stay crisp. Grab one and walk to the waterfront.
Dinner Pick
The Daily Catch: Tiny, cash-only, and they serve pasta in the skillet. You will be sitting elbow-to-elbow, but the calamari is legendary.
Bricco
"If you want the white tablecloth experience, go to Bricco. The espresso martini is arguably the best in the city."
Improv Asylum
Hanover Street
"Located in the basement of a CVS (classy, we know). It’s fast-paced, interactive, and often hilarious. There is no better way to break the ice than laughing at a stranger's expense together."
Late Night Laughs.
After the cannoli, head down the street for a show. The midnight shows are raunchy, the crowd is rowdy, and it’s the perfect antidote to a stiff dinner date.
The "NXT" Cast
Every Wednesday night. It's the up-and-coming cast. Tickets are cheaper ($15), the energy is hungry, and you might see the next SNL star before they get famous.
Bleacher Bar
Under the Centerfield Seats
"It’s the coolest bar in baseball. A garage door opens directly onto the outfield. You are literally eye-level with the grass. Even if there isn't a game, looking out at the empty, historic park is magical."
Fenway Park.
It’s the oldest ballpark in America. The energy on Jersey Street on game day is electric. It’s loud, passionate, and quintessentially Boston.
Sweet Caroline
In the middle of the 8th inning, the whole crowd sings. It’s cheesy, yes. But singing it with a date and 37,000 other people is a bonding moment.
Harbor Way
The Innovation District
"This is the 'New Boston.' Glass towers, rooftop bars, and the ICA. It feels less like 1776 and more like 2076. The Harborwalk offers stunning views of the skyline from across the water."
The Seaport.
If you want cocktails with a view, come here. It’s breezy, expensive, and sleek.
Lookout Rooftop
Atop the Envoy Hotel. The view of the downtown skyline glowing at sunset is unmatched. It’s a scene, so dress up.
The ICA
The Institute of Contemporary Art. On Thursday nights, it's free (with tickets). The cantilevered building hangs right over the harbor.
The Courtyard
"Hidden in the center of the building is an open-air Italianate courtyard with a fountain. It serves afternoon tea and cocktails. It is the most peaceful spot in the Back Bay."
The Public Library. 📖
It is a "Palace for the People." The McKim Building is a masterpiece of Renaissance architecture. It feels more like a museum than a library.
Bates Hall
The iconic reading room with the green lamps and barrel-vaulted ceiling. It’s studious, quiet, and breathtaking.
Paris in Boston. 🍂
The Commonwealth Avenue Mall was modeled after the boulevards of Paris. It’s a mile-long canopy of elms and statues running down the center of the street.
Winter Lights
In the winter, every single tree is wrapped in white lights. Walking down the mall in the snow is the closest you’ll get to a Hallmark movie.
Magnolia Season
In early spring, the magnolias bloom pink and white. It only lasts about two weeks, but it is the most romantic fortnight of the year.
Architecture Walk
"You are flanked by the finest Victorian brownstones in America. Pick a house and make up a story about who lives there. It’s a classic date game."
The Courtyard
Venice in Boston
"It is a Venetian palace dropped into the Fens. The indoor courtyard blooms year-round with nasturtiums and orchids. It is arguably the most romantic room in New England."
Explore The Palace →Isabella Stewart Gardner.
Known for its stunning art and the famous 1990 heist (the empty frames still hang on the walls). It’s mysterious, lush, and quiet.
The Glass Globe
Christian Science Plaza
"You literally walk inside the world. It’s a three-story stained glass globe built in 1935. The acoustics are wild—you can whisper at one end of the bridge and be heard perfectly at the other."
The Mapparium.
It is one of Boston's strangest and most beautiful attractions. The map hasn't changed since 1935, so you'll see countries that no longer exist.
The Reflecting Pool
After the tour, walk outside to the massive reflecting pool in the Christian Science Plaza. At night, it’s serene, lit up, and usually empty.
The Seasonal
Strategy. 📅
The Big Chill
Nov-MarBoston winters are brutal but beautiful. Stay indoors or embrace the ice.
- ● Frog Pond Ice Skating
- ● Cocoa at L.A. Burdick
- ● Harvard Art Museums
River Season
Apr-OctThe city turns green and gold. The best dates are on the water or in the parks.
- ● Swan Boats (Public Garden)
- ● Red Sox Games
- ● Hatch Shell Concerts
The Oyster
Hour.
We are currently shucking our way through the city to find the best $1 oyster deals, the freshest lobster rolls, and the hidden speakeasies of the South End.
Fenway Bars
Game Day Dates
South End
Brownstone Dining
Partner Deals
Exclusive discounts
Own a Great Boston Spot?
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