Top 12 Romantic Things to Do in Boston

Last Updated on February 11, 2024 by Emily Johnson

From historic landmarks to scenic harborsides, Boston sets the stage for romance with old-world ambience. Cobblestone streets lined with gas lamps, intimate cafes, cocktail lounges humming with Sinatra tunes and posh hotels catering to couples make Beantown a darling destination to share with someone special.

Top of the HubDining with city views
Trinity ChurchWhispering gallery
Boston HarborTall ship cruise
Improv AsylumLive comedy
Exhale SpaCouples massages
Fenway ParkBaseball game
Newbury StreetDessert stroll
The MappariumCultural visit
ImprovBostonComedy shows
North EndCannoli tasting
Whale WatchingHarbor adventure

Use this insider’s guide to create magical memories experiencing Boston’s most romantic attractions and activities.

Toast at Top of the Hub Restaurant & Lounge

Name and Location: Located on the 52nd floor of the Prudential Tower in Boston’s Back Bay, Top of the Hub Restaurant & Lounge offers unmatched city views through floor-to-ceiling windows.

History and Significance: Open since 1947, Top of the Hub has maintained its status as Boston’s premiere fine dining destination for panoramic vistas, especially sunset, coupled with exceptional contemporary New American cuisine and superlative service.

What to Expect: The award-winning restaurant impresses couples with refined dishes as vibrant as the 360-degree scenes over the city from a table or plush lounge seating. Toasting heightens the ultra-romantic ambiance against the glittering urban sprawl.

Visitor Information: Dinner reservations are essential, with strict dress code. Valet parking available for a fee. Closed some holidays. Craft cocktails, wine and live jazz further the upscale experience.

For stunning city views with your sweetheart, make reservations at Top of the Hub bridging the 52nd floor between Back Bay’s Prudential Tower and Copley Place. Beside breathtaking vistas spanning the Charles River to Fenway from vaulted windows, couples savor innovative New American cuisine paired with fine wines served alongside smooth jazz trios. Their signature martinis provide additional atmospheric enhancement at this special occasion icon.

Whisper Sweet Nothings through the Whispering Gallery at Trinity Church

Name and Location: Trinity Church is a historic Episcopal church built in 1877 near Copley Square whose interior architecture includes an acoustic quirk allowing whispers to be heard clearly from opposing corners.

History and Significance: The church’s distinctive late-19th century Romanesque style sanctuary designed by renowned architect H.H. Richardson contains a sonic effect beneath the central dome where whispers audibly transfer from one archway corner to its farthest diagonal opposite.

What to Expect: Sweethearts can descend side staircase nooks to opposite corners and whisper intimate nothings that transmit astonishingly across the open space to be heard privately, creating an acoustical illusion suitable for quiet connection within ornate surrounds.

Visitor Information: Trinity Church offers self-guided tours when no services are occurring. Validated two-hour parking available at nearby garages. Weekday visits less crowded.

Acoustic architecture makes Trinity Church’s whispering gallery a long-standing date destination. The intricate 1877 architectural detail in the church’s interior dome carries sounds from one corner to the other allowing sweethearts to exchange intimate expressions across the corridor much to the amusement of eavesdropping tourists. After testing the glowing granite gallery, step outside to photograph the picturesque National Historic Landmark finished in 1877 as an icon of worship.

Cruise Boston Harbor Aboard a Tall Ship

Name and Location: The 80-foot schooner Liberty Clipper sets sail daily out of Boston Harbor on scheduled public and private sailing trips touring historic sites around the harbor and Massachusetts Bay.

History and Significance: A replica of 1850s-era tall ships, the Liberty Clipper continues the sailing tradition Boston was founded upon while offering an experiential link to its rich maritime roots. Special sunset cruises make occasions more romantic.

What to Expect: Passengers help hoist sails or sit back admiring sea vistas on two or three hour narrated trips around the harbor and islands accentuated by refreshing salt air breezes. The relaxed pace fosters leisurely couple conversations against classic nautical splendor.

Visitor Information: Regular public trips occur April through October only. Private charters available year-round for fees. Easy boarding access from downtown water transportation pier.

Rekindle romance on the high seas together thanks to sailing tours aboard tall ships offering intimate Boston Harbor cruises. Relax on deck with a complimentary drink in hand appreciating sea breezes and panoramic city skylines from Boston to Charlestown. Special sunset sails feature live music and spectacular views providing perfect backdrops for stealing kisses as golden light dances off rippling waters for a nautical-themed date.

Catch Comedy at Improv Asylum

Name and Location: On Boston’s Theater District edge at Faneuil Hall Marketplace, Improv Asylum delivers hilarious improvisational skit comedy within an intimate 108-seat North End basement theater.

History and Significance: Founded in 1998 by 4 local comics, Improv Asylum grew into a Boston staple famed for lightning fast spontaneous shows crafted from audience suggestion ensuring every experience uniquely unfolds fueled by raw witty reactions between the quick-thinking troupe.

What to Expect: Rotating performers chime in unpredictably on quirky concepts invented on the spot for 75 minutes of sharp, smart comedy that routinely leaves audiences doubled over joyously at its anything-goes inventiveness and wit on full comedic display off the cuff.

Visitor Information: Shows run Wednesdays-Sundays year-round with two performances most nights. Ticket prices start around $25 per person. Food and drinks available before shows or at intermission.

Laughter fills the underground theater at Improv Asylum where you can catch live comedy nights alongside your sweetie. The cabaret-style venue pairs drinks with an ever-changing line-up of original skits focused on poking fun at Boston’s quirks performed by the venue’s improvisational troupe. The fast-paced shows eliciting big laughs, audience participation and musical numbers make for thoroughly entertaining evenings out enjoying intimate seating ideal for date nights.

Luxuriate Together at Exhale Spa

Name and Location: Exhale Mind Body Spa offers award-winning wellness spa treatments across 3 floors of their chic flagship Back Bay location blocks from Copley Square in Boston.

History and Significance: Since opening in 2003, Exhale’s expert staff have provided thousands of guests unparalleled massage, skin, nail and healing services by integrating therapeutic techniques into every spa experiencebolstered further by the tranquil vibe of their Zen-inspired space.

What to Expect: Side-by-side massages allow couples to benefit from enhanced circulation, stretched muscles and awakened senses together in a refined setting also offering restorative facials, mani/pedicures and healing rituals designed to soothe, balance and renew wholly.

Visitor Information: Online booking recommended for preferred appointments. Spa packages, special membership rates and validated parking ease visits. Arrive early to enjoy amenities like steam, showers and tea lounge.

Couples massages take pampering to the next level at Exhale Spa nestled alongside luxury shops inside the sleek Fanueil Hall area. Choose from an array of globally inspired relaxation rituals like fusion massages infused with reiki energy healing or Ayurvedic treatments harnessing essential oils. Side-by-side spa services enhance intimacy, especially when extending the experience from massage tables to infrared saunas or soaking tubs for restoring Balance.

Catch a Game at Fenway Park

Name and Location: Home of the Boston Red Sox since 1912, Fenway Park is a revered baseball landmark hosting 81 games a season within its uniquely asymmetrical green confines off Kenmore Square.

History and Significance: The oldest operating MLB ballpark filled with distinct quirks like the iconic Green Monster wall, Fenway maintains an electric atmosphere during games steeped in over a century’s worth of legendary moments and championships that true fans rabidly relive.

What to Expect: Watching the Sox play their longtime AL East rivals before Fenway’s emerald grass and brilliant red seat backs connects New Englanders through generations of memories established cheering amongst Fenway’s faithful during dazzling hits sailing over fences and spectacular catches along foul lines.

Visitor Information: Guided tours are available on non-game days. Tickets are compete online with scalpers outside park. Recommend taking trains as parking is extremely limited.

Experience America’s beloved pastime as a team during a competitive Boston Red Sox Game at legendary Fenway Park. Since 1912 New England baseball fans have packed these historic stands cheering walk-off homeruns and World Series victories together making Fenway bucket list sporting fun. But even outside October play-off fever, seeing the Green Monster up close while cuddled enjoying hot dogs and singing “Sweet Caroline” during the 7th inning stretch makes regular season match-ups special.

Stroll & Share Desserts along Newbury Street

Name and Location: Newbury Street spans eight walkable blocks across Boston’s Back Bay brimming with boutiques, galleries, restaurants and cafes perfect for window shopping and sharing sweets.

History and Significance: Since the 19th century when Copley Square sparked development, Newbury Street emerged as the ultimate leisurely Boston shopping thoroughfare featuring chic storefronts alongside posh brownstones and plazas with performers lining pedestrian-only lanes.

What to Expect: couples can meander down Newbury admiring diverse architecture and couture while stopping leisurely to indulge treats from an array bakeries and chocolatiers or linger outside patios with drinks watching street entertainment unfold spontaneously against vibrant bustling city backdrops.

Visitor Information: Accessible year-round, Newbury stays liveliest spring through fall, especially on temperate weekends. Garaged parking available via side streets otherwise everything is walkable from nearby T stops.

Upscale shopping lines Boston’s iconic Newbury Street also offering charming cafes perfect for intimate walks sealed with sweets. After browsing galleries and boutiques together duck into places like Stephanie’s bakery to split rich chocolate mousse cake or Trident Booksellers & Cafe to discuss novels over hot espresso accompaniments. Newbury Deluxe moonlights as a craft beer bar if you’d rather debate hops and malts content strolling under string lights lining cobblestone sidewalks after dark.

Take in Culture at The Mapparium

Name and Location: The three-story Mapparium globe is the iconic centerpiece of the stained-glass Mary Baker Eddy Library in Boston’s Fenway neighborhood comprising a one-of-a-kind illuminated world map within a giant glass orb visitors walk inside.

History and Significance: Unveiled in 1935, the Mapparium’s pioneering design envisioned by architect Chester Lindsay Churchill comprises over 650 stained glass map segments encasing a hollow sphere around a bridge creating unique acoustic and visual effects still intriguing and educating visitors about geography 85+ years later.

What to Expect: Stepping inside the Mapparium’s interior three-dimensional world map magnifies the glowing colors wrapping visitors in the center of continents and oceans accurate to the 1930s while hushed whispers traverse the architectural sphere astonishingly. The experience remains singular decades on.

Visitor Information: Thirty-minute guided Mapparium tours run daily for fees. Entry includes access to the adjacent Mary Baker Eddy library and monitor screens playing footage of the bridge’s 1930s debut.

The Mapparium immerses couples within a three-story, stained glass globe inside the Christian Science Mary Baker Eddy Library. Walk through the bridge-like 1935 architectural feat spanning an enormous stained-glass map of the world circa 1935 to whisper secret travels plans privately thanks to the acoustic peculiarity allowing hushed phrases spoken from across the room still be heard. Bring a camera to capture cute kissing snapshots against the illuminated 30-foot glass globe from within for romantic portraits with a twist.

Cozy Up for Comedy at ImprovBoston Comedy Theater

Name and Location: ImprovBoston in Cambridge’s Central Square is an intimate 90-seat black box theater hosting improv comedy shows every night using audience suggestion to invent completely unscripted skits and scenes on the spot.

History and Significance: Launched in 1982, ImprovBoston grew renowned for igniting Boston’s improvised comedy scene over decades through hosting fearless performer showcases and catalyzing troupes like acclaimed Blue Man Group’s origins before relocating into its custom performance space’s current location in 2000.

What to Expect: Audiences immerse in original concepts invented extemporaneously – cheering talent tackling scenes, musicals or experimental mashups fueled solely on spontaneous wit and creativity channeled through their immediate reactions with fellow players onstage full of amusing surprises.

Visitor Information: Shows usually run under 2 hours with ticket prices around $25 and discounts for students or late-night shows. Full restaurant menu and bar service available.

Seeking laughs together late-night? ImprovBoston comedy club stages rowdy sketch and stand up shows Thursday through Saturday inside a historic basement theater. Signature improv comedy battles like “Stand Up Cage Match” push boundaries for cheeky entertainment paired well with local brews to fuel the atmosphere. Intimate cocktail tables encourage couples to cozy up beneath dangling lights for an unconventional yet amusing date out until midnight.

Cross the North End for Cannoli

Name and Location: Boston’s North End neighborhood is regarded as the city’s authentic Little Italy district bustling with Italian cafes, bakeries and restaurants doling out specialties like beloved traditional cannoli pastries.

History and Significance: Home to wave after wave of Italian immigrants since the late 1800s, the North End’s narrow vibrant streets house many longtime family-owned eateries crafting cherished Old World desserts and cuisine from recipes carried on through generations of Boston’s Italian community now mainstays of local gastronomy tastes.

What to Expect: Couples can sample cannoli and other Italian delicacies by peeking into fragrant bakeries while navigating the storied neighborhood’s roads lined by historic brick buildings in between sit-down restaurants dishing hearty comfort food and glasses of wine nightly.

Visitor Information: The North End stays lively year-round offering plenty of quality options. Validate parking garage tickets for discounts to accommodate for limited street parking or take public transit.

Little Italy thrives in Boston’s postcard-perfect North End neighborhood where Old World ambience sets an intimate tone strolling narrow streets holding hands past historic churches and Italian cafes. Family-run restaurants light up Hanover Street but fantastic dessert shops like Maria’s Pastry Shop, Modern Pastry and Bova’s Bakery keep lovebirds returning to split crunchy cannolis overflowing with sweet ricotta filling or pistachio macaroons dusted in powdered sugar.

Whale Watch off Boston Harbor

Name and Location: Boston Harbor Cruises operates whale watching and sightseeing tours onboard mega-boats departing downtown’s Long Wharf daily during peak seasons offering chances to spot migrating whales offshore.

History and Significance: As an eco-friendly company prioritizing education and research, Boston Harbor Cruises commits crews specially trained by on-staff naturalists to locate whales following food sources on their migratory paths across Cape Cod and Stellwagen Banks National Marine Sanctuary.

What to Expect: Departing Boston’s bustling waterfront, couples peer through salt-flecked windows and deck rails scouring for telltale spouts in the distance before a captain sounds alerts for behemoths cresting waves soon after – a thrilling chance sighting giants gracefully against blue seascapes.

Visitor Information: Whale watches operate April-October during seasonal migrations when sightings peak. Rough seas can cause cancellations. Reservations ensure spots on popular cruises.

Setting sail together in search of whales and dolphins shows your shared wild side while enjoying time on the water. Three-hour whale watching tours depart from Long Wharf placing lovebirds port-side to spot humpbacks emerging from the deep while a guide provides narration on sea life spotted enroute. Days not graced with sightings still deliver saltwater kisses above deck alongside tasty snacks from the onboard bar to sustain couples until golden hour sea breezes blow your way.

Iconic landmarks, intimate escapes and cultural activations make Beantown a darling destination for romantic getaways. From Fenway ballgames to North End strolls sealed with cannoli kisses, these signature Boston experiences crafted for couples amplify affection with their incorporation of history, entertainment and scenery. Use these insider tips when planning quality time together in one of America’s most amorous cities.

Leave a Comment