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Date Ideas in Boston
20s / 30s / Alternative / Bar / Beer
Party Earth Review A hidden gem with a cult following of hip young locals, Sacco’s Bowl Haven offers a unique old-school night out at equally old-school prices. First opened in 1939, the venue has retained its original focus on candlepin bowling, though new owners have updated the place by adding a wood-fired pizza parlor and alcohol – an ... more
45 Day Street
Somerville, MA 02144
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80s Music / 90s Music / Bar / Chic
Party Earth Review Maybe the only place in town with both crystal chandeliers and tater tots, The Brahmin is an elegant 20s-style speakeasy with one foot firmly planted in modern day. Named for the wealthy, politically prominent families of neighboring Beacon Hill – the illustrious “Boston Brahmins” – this shabby chic bar is a jumble of high ... more
33 Stanhope Street
Boston, MA 02116
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Bars / Birthday Parties / Cafés
Party Earth Review Home to Boston’s vibrant Italian district and many historic landmarks, the North End and its narrow cobblestone streets draw everyone from pasta lovers and tourists to wine-drinking partiers. Though gentrification has attracted a growing number of young professionals, the small neighborhood is still home to a high concentration ... more
I-93 and Commercial Street
form the rough boundaries of the North End
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Alternative Rock / Artists / Bar
Party Earth Review Even the most tattooed of Jamaica Plain’s routinely plaid-clad denizens can tire of swilling PBR, and that’s where Canary Square comes in. This cozy gastropub attracts much the same crowd of hipsters, artists, and laid-back pals as the authentic and popular Brendan Behan's Pub up the street, but pumps up the food and alcohol ... more
435 South Huntington Avenue
Jamaica Plain, MA 02130
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30s / Affluent / Artsy / Bar / Beer
Party Earth Review A quaint and lively destination for fashionable city diners, the Franklin Café attracts an animated clientele of affluent locals, stylish couples, and trendy hipsters. With space for only forty people, the venue maintains a comfy yet chic atmosphere, backed up by dim lighting, red mirrored walls, and black leather booths ... more
278 Shawmut Avenue
Boston, MA 02118
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Ambient / Bar / Brunch / Burgers
Party Earth Review Although Upstairs on the Square is only a few steps above Winthrop Square, its cupcake pink walls, gold chandeliers, and endless fresh flowers transport patrons far from the college town below. After ascending the leopard-striped staircase, preppy grad students and sophisticated professionals unwind with a fancy cocktail ... more
91 Winthrop Street
Boston, MA 02138
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20s and up / After Work / Chill
Reviewed by Laura A.
"Spend an afternoon at The French Room at the Taj Hotel in Boston for a one of a kind experience. Downton Abbey fans can rejoice at having a place that ..." more
15 Arlington Street
Boston, MA 02116
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Anything goes / Artsy / Brunch
Party Earth Review A tribute to the sausage-slung shops of old-world Europe, The Butcher Shop is a warm and stylish wine bar and eatery that attracts a diverse and amiable clientele of oenophiles, music school hipsters, and in-the-know tourists looking for upscale fare and a relaxed vibe. Patrons peering into the large front windows of the ... more
552 Tremont Street
Boston, MA 02118
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After Work / Ambient / Bar Food
Party Earth Review Despite the prevalent stereotype that hotel bars are soulless affairs only intended for temporary guests, the historic Copley Square Hotel’s minibar has become a go-to for plenty of chic locals looking for a chill spot to start the night. In the post-work hours, trendy Back Bay professionals claim the dark ... more
Copley Square Hotel
51 Huntington Avenue
Boston, MA 02116
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30s / 40s / Artsy / Bohemian / Couples
Party Earth Review Boasting an outstanding wine selection and an intimate bistro atmosphere, Les Zygomates is a prime date night destination for those looking for a taste of Paris near downtown Boston. The business people and artsy types who settle in at the candlelit tables shouldn’t be fooled by the delicious bistro fair and perfectly prepared ... more
129 South Street
Boston, MA 02111
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Beer / Beer Lovers / Boat Party
Info The Classic Harbor Line is dedicated to providing the most impeccably luxurious and hospitable sailing experience in Boston. Guests can look forward to the privilege of being escorted on a breathtaking excursion aboard the most elegant sailing vessel in Boston Harbor, the schooner Adirondack III. If you’re a first ... more
60 Rowes Wharf
Boston, MA 02110
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Boston Date Ideas Overview
Often considered to be one of the more “European” style cities in the U.S., Boston abounds with romantic options that make it perfect for date ideas.
The Boston Public Garden, an arboretum that contains dozens of species of trees, also is home to the generations-old swan boats, which are paddled around the small pond inside the park during the warmer months of the year. The paddle boats have wooden benches for seating, perfect for cuddling up next to the object of one's affection as the gorgeous scenery is revealed all around.
Post Office Square Park, in the Financial District, contains fountains, brick walkways, benches, a gorgeous vine-covered pergola, and dozens of species of plants and trees. Since the area is so quiet on the weekends, it is also on the route of the horse-drawn carriages that give rides to folks leaving from the Quincy Market area.
Boston even has its own gondola rides on a small inlet channel of the Charles River. The boats dock not far from the Back Bay and Charles Street of the Beacon Hill neighborhood, where some of the city's most ambiance-rich restaurants are contained. Those in search of great Boston date ideas would be smart to stick towards these neighborhoods when in search of dinner plans.
Popular Boston Neighborhoods
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