Revolution was born in Boston. The capital city of Massachusetts is the largest city in New England and the place where the seeds of the American Revolution were first sown. Visitors can explore this rich history through iconic sites like the Boston Massacre site, where tensions with British soldiers erupted in 1770, and the Old South Meeting House, where the infamous Boston Tea Party was planned. The Battle of Bunker Hill, the first major conflict of the Revolutionary War, took place nearby. By walking the famous Freedom Trail, visitors can trace the steps of patriots like Paul Revere, whose midnight ride warned of British advances. In short, Boston is a living museum of America's fight for independence, ripe for exploration.
Boston’s revolutionary momentum continued through the later years as the city became a trailblazer with a reputation for doing its own thing. Boston had the first public park in the U.S., the first subway, the first public school, and the first openly gay elected state official in the U.S. Not to mention, Boston is home to the United States' most prestigious university, Harvard.
The spirit of liberty lives on in the vibrant LGBTQ+ community, and it's no coincidence that Boston also has the largest LGBTQ+ population on the East Coast—even more so than nearby Provincetown. These are all compelling reasons to add Boston as a city to visit for anyone really wanting to delve into the roots of the U.S. and experience some Boston hospitality in the process. Just don’t try mimicking the accent…
Table of Contents
- General Tips
- Airport Transfer and Transportation
- Gay Hotels in Boston
- Sightseeing & Activities in Boston
- Gay Tours in Boston
- Restaurants and Cafes
- Boston Gay Bars and Clubs
- Boston Gay Saunas & Cruising Bars
- Gay Beaches in Boston
- Gay Events in Boston
- Day Trips from Boston
General Tips
Boston is a great city to visit any time of the year, but winters are cold—brutally cold! You can expect a lot of snow, so dress accordingly. Summers, on the other hand, are warm but not unbearable, making it the best time to visit for those interested in watersports and outdoor activities. Spring and fall offer the opportunity to do a bit of everything in mild weather, with fewer crowds and cheaper hotels.
Boston is smaller than you’d expect, at least in the city center, so walking—or cycling—is most people’s preferred form of transportation. It’s also the best way to see everything the city has to offer. Sure, there are the obvious sights that line the Freedom Trail, but Boston is all about those local treasures you find simply by exploring the city, from photogenic streets with 19th-century houses to quaint restaurants and cafes sporting that authentic Boston feel.
If you’re trying to see all there is to see in a limited time, consider getting the Go Boston Pass. Choose between 1- to 7-day passes for unlimited access to the big attractions.
Airport Transfer and Transportation
Getting from Boston Logan International Airport to the city center is quick and convenient. The Silver Line bus (SL1) is a free and easy option, connecting all the terminals at the airport to South Station, where you can transfer to other subway lines. The ride takes about 20 minutes. Alternatively, taxis and rideshare services like Uber and Lyft are readily available outside each terminal and offer a direct route to your destination. For a scenic arrival, the Logan Express Water Shuttle provides a transfer across the harbor and is a wonderful way to enter the city.
Once in the city, Boston’s public transportation system, known as “the T”, is efficient and easy to navigate, with subway, bus, and commuter rail options to help you explore the city’s many neighborhoods. Walking and biking are also great ways to experience Boston’s compact, pedestrian-friendly layout.
Gay Hotels in Boston
Luxury
Liberty Hotel – A luxurious boutique hotel in a former jail shouldn’t work, yet this hotel manages to balance modern class with quirky features that nod to its former self—from the exposed brick lobby to the iconic rotunda and even leftover cells. Don’t worry though, the rooms and facilities are as luxurious as you’d expect from a five-star hotel, and its location on Beacon Hill means it offers sweeping views of the Boston skyline. The hotel boasts six on-site restaurants serving everything from Italian to American to seafood cuisine, each with quirky names and unique features, such as Clink (with jail bars) and Alibi (with mug shots of celebrities on the walls).
Mid-Range
The Revolution Hotel – Viva la Revolution! This urban boutique hotel boldly displays Boston’s revolutionary pride. You can see it in the literal flag on the door, the pictures of Boston revolutionaries on the walls of its cafe, the 65-foot mural in the foyer, and the “Innovative Tower,” an art piece celebrating Boston’s innovations that spans three floors. The hotel rooms, on the other hand, are homely yet stylish, with loft, suite, and bunk bed rooms for groups. There's a Mexican restaurant on-site, a trendy coffee shop, and a fitness center. Needless to say, with such a revolutionary theme, the hotel is extremely LGBTQ+ friendly and is centrally located in South End, just a short walk from the main gay nightlife.
Clarendon Square Bed and Breakfast – Size isn’t everything, and this petite, yet luxurious, bed and breakfast masterfully combines chic with homely. Located in an 1867 townhouse on a tree-lined street in South End, it offers the full Boston hospitality experience. The rooms are comfort incarnate, and the house features a library, a parlor area, and even a rooftop hot tub.
W Boston – Boston’s chic theater district is known for music, art, and fashion. This hotel epitomizes that with its stylish and contemporary interior. It is especially known for being very tech-forward in both its rooms and unique events like Tablemation—an animated, immersive 3D dining experience featuring a three-course meal prepared by animated chefs. The hotel also features a fitness center, bar lounge, business center, and spa.
Budget
Oasis Guest House – This gay-owned guest house in the Fenway neighborhood—nicely located between the main attractions and not far from Harvard—is as cozy as it gets. The rooms all have that homely touch, and some even have shared terraces. The service feels very personalized, warm, and welcoming.
Sightseeing & Activities in Boston
Freedom Trail – This 2.5-mile-long red-brick path takes you through 16 significant historical sites, offering a glimpse into the American Revolution's birth. Starting at Boston Common, the oldest public park in the United States, the trail guides you through landmarks like the Massachusetts State House and Park Street Church. Key stops include the Granary Burying Ground, where notable figures like Paul Revere and Samuel Adams are buried, and the Old South Meeting House, where the Boston Tea Party was organized. The Old State House, the site of the Boston Massacre, and Faneuil Hall, known as the “Cradle of Liberty,” are also highlights. The trail concludes at the Bunker Hill Monument, commemorating the first major battle of the Revolution, and the USS Constitution, the world's oldest commissioned naval vessel still afloat. Book tour →
Boston Public Garden and Swan Boats – America’s first public botanical garden from 183 is located in the heart of the city and features beautifully landscaped gardens, winding pathways, and a picturesque lagoon. The garden is famous for its vibrant flower beds and the iconic equestrian statue of George Washington.A highlight of visiting the Public Garden is the Swan Boats, a cherished Boston tradition since 1877. These pedal-powered boats, shaped like graceful swans, offer a peaceful 15-minute ride around the lagoon, providing stunning views of the surrounding greenery and the charming Make Way for Ducklings statues. Operated by the same family for over a century, the Swan Boats are a quintessential part of a Boston experience,
Boston Tea Party Ships & Museum – Relive the event that sparked the American Revolution at the Boston Tea Party Ships & Museum. Located on the Congress Street Bridge, this museum offers an interactive journey back to December 16, 1773, when American colonists protested British taxation by dumping tea into Boston Harbor. The museum features full-scale replicas of the original tea ships, the Beaver and the Eleanor, where visitors can board and participate in reenactments of the tea-dumping event. Inside the museum, you'll find interactive exhibits, rare artifacts, including one of the original tea chests, and multimedia presentations that vividly recount the events leading up to the American Revolution. Everything concludes with a stop at Abigail’s Tea Room, where you can sample the teas that were thrown overboard. Book tour →
Harborwalk & Boston Harbor Cruises – The Harborwalk is a scenic public walkway that stretches along Boston's waterfront, offering the best of the harbor, the city skyline, and access to various attractions. Spanning over 40 miles, it connects parks, art installations, historical markers, beaches, wharves, and piers. Boston Harbor Cruises offer everything from historical sightseeing tours to sunset cruises, whale watching, and even ferry services to nearby islands. Through these you can sail out to landmarks like the Boston Tea Party Ships, Fort Independence, and the Boston Light, the oldest lighthouse in America. Book tour →
Isabella Stewart Gardner Museum – Founded by the eccentric and visionary art collector Isabella Stewart Gardner, the museum is housed in a stunning Venetian-style palace, complete with a lush central courtyard that blooms year-round. The museum's collection includes over 7,500 works of art, ranging from European paintings and sculptures to Asian and Islamic art, rare books, and decorative arts. The museum is perhaps best known for its intimate and personalized atmosphere, with each room arranged according to Gardner's distinct vision, offering a deeply personal experience. Visitors can explore masterpieces by artists such as Titian, Rembrandt, and Sargent, all displayed as Gardner herself intended. The museum also gained fame for the infamous art heist in 1990, where 13 pieces, including works by Vermeer and Degas, were stolen and remain missing.
Museum of Fine Arts – One of the most comprehensive art museums in the world. With over 500,000 works, its vast collection spans centuries and cultures, featuring masterpieces from ancient Egyptian artifacts to contemporary art. They also often have special exhibitions highlighting LGBTQ+ artists and themes.
Newbury Street Shopping – Indulge in some retail therapy on Newbury Street, Boston’s premier shopping destination, stretching eight blocks through the heart of the Back Bay neighborhood. This charming, tree-lined street is home to a mix of high-end boutiques, trendy fashion stores, art galleries, and quaint cafes. Book tour →
Beacon Hill – Boston's most picturesque and historic neighborhood, known for its cobblestone streets, gaslit lanterns, and beautifully preserved Federal-style row houses. Located just a short walk from downtown. At the heart of Beacon Hill is Louisburg Square, a private park surrounded by elegant townhouses that have been home to some of the city's most prominent residents. The neighborhood is also famous for Acorn Street, often cited as one of the most photographed streets in America. Book tour →
Harvard University and Park – Located in Cambridge, just across the Charles River from Boston, Harvard University is the oldest institution of higher education in the United States, founded in 1636. For tourists, a visit to Harvard offers a chance to explore a campus rich in history, culture, and academic prestige. The university's red-brick buildings, ivy-covered walls, and historic landmarks like Widener Library and Memorial Hall provide a picturesque setting. Adjacent to Harvard Yard is Harvard Square, a bustling area filled with shops, cafes, and street performers, making it a lively spot for tourists to explore. Nearby, the Harvard Art Museums offer a vast collection of world-class art. For a relaxing stroll, the nearby Harvard Yard provides a peaceful green space to unwind and enjoy the beauty of this iconic university setting. Book tour →
Quincy Market – Located in the heart of Boston's historic Faneuil Hall Marketplace, is a bustling hub of food, shopping, and entertainment. Opened in 1826, this iconic market is housed in a grand, columned building that reflects the city's rich history. Inside, across its two floors you'll find a vibrant array of food vendors offering everything from classic New England clam chowder and lobster rolls to international cuisine and sweet treats. Note that the Cheers Bar inside is a fake – the true bar where the sitcom was filmed is now found in the basement of Hampshire House in Beacon Hill. Book tour →
Gay Tours in Boston
Rainbow Revolutionaries with The Freedom Trail – There are countless tours that follow the Freedom Trail, but this one—not only having the coolest name—tells the stories of the hard-earned liberty of Boston’s LGBTQ+ community and the romantic stories of queer individuals in Boston’s history. Hear all about political milestones for LGBTQ+ rights and the gay romances of some of Boston’s most famous individuals, from literary giants to a world-renowned actress and even a Revolutionary War hero. Book tour →
Boston’s LGBTQ Past with Boston by Foot – Boston’s LGBTQ+ history is extensive, and this 90-minute tour travels in the literal footsteps of Boston’s 19th and 20th-century LGBTQ+ historical figures. It explores Ralph Waldo Emerson and Walt Whitman's walks along the Common, Charlotte Cushman’s cross-dressing roles, World War II bars and baths, and the AIDS Memorial Quilt project. Book tour →
Restaurants and Cafes
Union Oyster House – Located in Boston's historic district, it is the oldest continuously operating restaurant in the United States, having served customers since 1826. This iconic eatery offers a rich blend of history and classic New England cuisine, specializing in fresh seafood, particularly oysters. The restaurant's cozy, wood-paneled interiors and narrow staircases evoke the charm of early American taverns. It's not just a dining destination but a landmark, with ties to figures like Daniel Webster and John F. Kennedy.
Parish Cafe & Bar – Known for its unique menu featuring gourmet sandwiches crafted by Boston’s top chefs, Parish Cafe in Back Bay offers a casual dining experience with a full bar and outdoor seating. Each sandwich on the menu is a signature creation from a local chef, offering a diverse and inventive selection. Parish Cafe also offers a variety of craft beers, cocktails, and desserts.
The Friendly Toast – It’s never too late for brunch…or too early, for that matter. This vibrant and eclectic cafe serves it all day with quirky decor and a fun atmosphere. The menu is packed with comfort food favorites, making it a great spot in Back Bay for food and a sneaky mimosa. During peak times, it gets very busy, so be sure to make a reservation for those times.
Dbar – Dbar has the rare quality of being fully versatile, seamlessly transitioning from a sophisticated dining spot by day to a lively nightlife venue at night. It is known for its modern American cuisine, featuring a menu with fresh, locally sourced ingredients and dishes ranging from creative appetizers to hearty entrees. The restaurant’s elegant yet cozy ambiance is enhanced by its beautiful terrace area.
Davio’s Northern Italian Steakhouse – Davio’s offers an upscale dining experience that blends the flavors of Northern Italy with the elegance of a traditional steakhouse. The menu includes hand-cut steaks, fresh seafood, and handmade pasta, all prepared with the finest ingredients. The restaurant’s open kitchen adds a dynamic touch, allowing guests to observe the culinary artistry in action. Located, like many of Boston’s best restaurants, in Back Bay.
Flour Bakery + Cafe – Everyone loves a tart with a heart, and this beloved Boston establishment is known for its delicious pastries, fresh bread, and savory sandwiches. Founded by renowned pastry chef Joanne Chang, Flour offers a warm, inviting atmosphere perfect for a casual breakfast, lunch, or an afternoon treat. The menu features a variety of baked goods, from sticky buns and croissants to cookies and tarts, all made with high-quality ingredients. While there are multiple locations around the city, the one in the South End is especially popular with the LGBTQ+ community.
Atlantic Fish Co. – This premier seafood restaurant is known for its fresh, daily-caught fish and classic New England fare. With its dedication to freshness and exceptional service, Atlantic Fish Co. has been a staple in Boston’s dining scene for decades. The interior is classic, with a distinct Boston feel, and the menu features a wide selection of seafood dishes, including lobster, clam chowder, and expertly grilled fish, all prepared with the highest quality ingredients.
Boston Gay Bars and Clubs
Club Café – Affectionately known as Boston's “Cheers for queers,” Club Café has been a staple of the LGBTQ+ scene since 1983. The Back Bay venue functions as a restaurant during the day and transforms into a dance floor at night. They mix it up with live music, drag shows, RuPaul's Drag Race showings, DJs, and themed parties depending on the night.
The Alley – This intimate downtown gay bar is especially popular with the bear community and features pool tables, karaoke nights, and a spacious second floor with a dance floor playing cheesy music. They also serve food during the day.
Dbar After Dark – A fine dining restaurant that becomes a gay club at night every day of the week. Highlights are Show Tune Tuesdays, Karaoke Fridays and Magnum Saturdays.
Dani’s Queer Bar – An up-and-coming lesbian bar that promises to be something special. Dani's Queer Bar will host community-building events that showcase Boston’s queer culture and allow everyone to be their true and authentic selves. Watch this space!
Jacques Cabaret – Home to the best drag shows in town, this long-running venue offers nightly drag performances in a cozy, intimate setting, making it a favorite in the Boston LGBTQ+ scene. Located in Bay Village.
Cathedral Station – This gay sports bar in the South End has a neighborhood pub vibe. It’s also very spacious, with a bar area for watching games and playing pool, a separate dining area, and a large outdoor patio.
Midway Cafe – Not a gay bar per se, but a cool dive bar in Jamaica Plain that has live music and hosts LGBTQ+ nights. Their biggest event is “Queeroke,” a queer karaoke night with a DJ that is one of the longest-running queer nights in New England.
Boston Gay Saunas & Cruising Bars
Sadly, Boston City Hall seems to have a personal vendetta against bathhouses, and there are currently none to be found in Boston…yet. There aren’t any specific cruising bars either. A trip across to Provincetown is the way to go!
Gay Beaches in Boston
Kiki Beach (M Street Beach) – Let’s have a kiki…on the beach. Every Saturday throughout the summer, the gays lay claim to a stretch of sand on M Street Beach. All members of the LGBTQ+ community are welcome, and it's a great opportunity to make new friends, lovers, and enemies!
Gay Events in Boston
Boston Pride Parade and Festival – Boston is proud of its LGBTQ+ community and queer roots, and its Pride celebrations in mid-June are among the oldest in the country. The week-long festivities kick off with the raising of the pride flag at City Hall Plaza. From then on, there are block parties, cruises, bar crawls, themed street parties (like the space-themed Big Gay Dance Party), drag shows, and more as the week progresses. On the final Saturday, it culminates in a parade beginning in Copley Square and ending at Boston Common, followed by a final block party at City Hall Plaza.
Boston Urban Pride – Taking place over the July 4th weekend, Boston Urban Pride focuses on celebrating the Black LGBTQ+ community. The event features activities such as Youth Pride, a Welcome to Boston Tour, an All Black Boat Ride, and the Black Pride Parade, culminating in a Music and Arts Festival.
Boston Trans Resistance March and Vigil – Typically held in June, this event honors the lives and struggles of transgender individuals, particularly those who have faced violence and discrimination. The march through Boston is followed by a vigil and speeches.
Day Trips from Boston
Salem – The legendary site of the 1692 witch trials is just a 30-minute drive from Boston or short ferry ride. Visitors can delve into the town’s grim history at the Salem Witch Museum, wander through its streets lined with 18th-century buildings, take a picture with the Bewitched Statue, and explore the hidden passageways of the House of the Seven Gables. Come for the witchy history, but also enjoy the galleries, unique shops, and waterfront restaurants. Book tour →
Provincetown (Cape Cod) – Just a two-hour ferry trip or a 90-minute car ride away, Provincetown is a charming seaside town that is completely taken over by the LGBTQ+ community during the summer months. With a population of about 3,000, this small New England getaway boasts 40+ gay guesthouses, 10+ gay bars and clubs, and 2 gay beaches, while also hosting a dozen or more LGBTQ+ events throughout the year. However, if you visit out of season, you’ll find a much quieter vibe and an opportunity to relax by the sea in the very place where the Pilgrims first landed all those years ago. Book tour →
Concord and Lexington – These neighboring towns, just a 30-minute drive from Boston, are rich in Revolutionary War history. Visitors can tour historic sites like the Lexington Battle Green and the Old North Bridge in Concord, where the first shots of the American Revolution were fired. The area is also home to beautiful nature trails and Walden Pond, made famous by Henry David Thoreau. Book tour →
Featured image by Kyle Klein.
Note: Some of these links are affiliates which means using them won’t cost you any extra but we do receive a small commission for each referral. You’re not obligated to use them but we appreciate it if you do. Thanks in advance for supporting this site if you choose to use our link!
Comment (0)