Boston Travel Guide

Boasting some 400 years of rich cultural heritage, Boston is arguably America’s oldest city—a place where near every park, building and museum has a time-honoured story to tell. And with a small, walkable downtown, it doesn’t take long to discover the fascinating history that permeates Boston’s narrow streets and beloved, shimmering harbour. Yet while Bostonians are mighty proud of their roots, they haven’t lost sight of their revolutionary, trailblazing ways—specifically as it pertains to the LGBTQ community. This was the first state to legalize gay marriage, after all, and let’s not forget ever-beloved gay Provincetown is just a hop across the Massachusetts Bay. While Boston’s traditional gayborhood still centres around South End and Tremont Street, you’ll find rainbow flags billowing throughout the town. Of course, no introduction to Boston is complete without a nod to their unwavering passion for local sports teams. From the Red Sox to the Celtics to the Bruins, there’s always a reason to do as the locals and cheer on Boston’s home teams. Now, without further ado, let’s get started with Mr. Hudson’s ultimate gay Boston guide.

Where to stay in Boston

For old-European charm in the heart of Boston’s sought-after Back Bay, The Eliot Hotel is a commendable choice. From the Beaux-Arts-style entrance to Italian marble countertops to decadent suites that include large living rooms and kitchenettes, The Eliot Hotel is pure luxury ideally situated on one of Boston’s most beautiful boulevards. From this location, you certainly won’t want for excellent dining options, but be sure to reserve a table at the on-site James Beard award-winning restaurant: UNI. Helmed by celebrity chef Ken Oringer, the foodie hotspot combines Japanese specialities with classic tavern fare. Another opulent Boston hotel that oozes with style is the XV Beacon, a boutique Beaux Arts property tucked away in quintessential Beacon Hill. Canopied beds, cosy fireplaces, and a stunning glass cage elevator (original to the building) are just a smattering of the smart, sexy details. Come for a romantic weekend escape—you’d be forgiven for never leaving the premises.

Photo: Sylvie Tittel

The Charles Hotel seamlessly combines rustic New England charm with upscale amenities to create a hotel stay that is uniquely Boston

In the centre of iconic Harvard Square, The Charles Hotel seamlessly combines rustic New England charm with upscale amenities to create a hotel stay that is uniquely Boston. Keep an eye peeled for the various original pieces of art on display, many commissioned specially for the property by local Cambridge artists. Continuing with the theme of the artwork, No. 284 is a 19th-century townhouse turned ultra-luxurious 23-room guesthouse that could quite easily be mistaken for an esteemed art gallery. From Picasso on the first floor to Warhol on the top, each guestroom gets its name from an artist; you’ll find their work adorning the walls inside. The lovely Brownstone building is tucked away on a quiet lane just steps from Newbury Street—Boston’s most prized shopping district.

Then there’s The Verb, a funky-fresh 1959 motor inn turned contemporary hotel that’s perfectly befitting of this Boston gay city guide. The Verb purposefully exudes major rock-and-roll vibes (and it does so quite well, might we add.) The music theme is evident as soon as you step foot in the lobby, where vintage music posters and a great album rack take centre stage. We love the sleek retro decor, which makes full use of black, white and vibrant pops of colour. Opt for a room gazing out to the pool and sundeck, a chic space worthy of any rock star.

Photo: Nik Lanus

Photo: Matthew Landers

Recommended hotels in Boston

Hotels

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Things to do in Boston

One of the best ways to get your bearings of Boston is via a walking tour. There are a few to choose from but go with Boston By Foot, a non-profit organization that promotes awareness of the city’s architectural heritage and history. Even better, their “Boston’s LGBT Past” walk is a fascinating deep-dive into the city’s gay and lesbian culture from the 1840s-1980s. Those who prefer independent activities might stroll the Equality Trail, a self-guided walking tour of Boston’s first Gay Pride March back in 1971. Take your Boston sightseeing to the North End for a tantalizing three-hour food tour your senses won’t soon forget. This is Boston’s Little Italy, where scrumptious markets, bakeries, and trattorias punctuate the narrow, picturesque streets. Far removed from inauthentic tourist traps, you’ll discover the best mom-and-pop eateries while indulging in delicacies like marzipan, lobster tails, cheeses—and, of course, wine. With all those steps you’ve put in, you’ll have earned the indulgence.

Boston Public Library | Photo: C. J.

This is Boston’s Little Italy, where scrumptious markets, bakeries, and trattorias punctuate the narrow, picturesque streets

Boston’s Museum of Fine Arts (MFA) isn’t exactly a well-kept secret, but our Boston travel guide would be remiss not to mention this expansive collection of world artefacts that collectively comprise the fifth largest museum in the United States. Try to spend at least a few hours, though know that will only brush the surface. Exhibits stretch from ancient Egypt to today; don’t miss the Korean art collection—it’s the largest outside Korea. Another clear example of Boston’s enduring legacy as the “Athens of America” is Boston’s Institute of Contemporary Art. The impressive glass-filled building overlooks the Harbor, a worthy enough reason to visit the museum alone. For something entirely unique, the Isabella Stewart Gardner Museum is a stunning “inside-out” Venetian-style palazzo and museum dating back to 1903. The exhibits draw from Gardner’s bohemian travels and passion for world cultures and include tapestries, sculptures, ceramics, and other global masterpieces. It’s a captivating glimpse into the life of Gardner, an eccentric millionaire who never lost her free-spirited enthusiasm for the world.

The Boston Gay Men’s Chorus (BGMC) is absurdly talented without ever taking itself too seriously; enjoying one of their world-class performances is a must for any gay Boston guide. Their repertoire spans the music spectrum, with everything from pop to show tunes to classics.

Gardner Museum | Photo: Isabella Stewart

Recommended experiences in Boston

Experiences

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Whale Watching Cruise from Boston

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Experiences

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North End Morning Food Tour with Local

2 hours

Experiences

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Martha's Vineyard: Day Trip from Boston

12 hours

Experiences

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Harbor Sunset Yacht Cruise

2 hours

Experiences

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Haunt and History Night Tour

1.5 hours

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What to see in Boston

If you only visit one of Boston’s architectural marvels, make it the Boston Public Library. This 1895 Renaissance Revival building is overflowing with magnificent statues, John Singer Sargent murals, and over 1 million rare books and documents. Whether you’re perusing first-edition William Shakespeare folios or simply soaking in the building’s artistic treasures, you’ll leave with a newfound appreciation for America’s first publicly supported municipal library. Keep your intellectual juices flowing with a visit to Harvard Yard, the geographic heart of one of the country’s most celebrated universities. The grassy area is undeniably beautiful while also buzzing with intellectuals; go for a stroll alongside storied buildings or hop into any one of the Universities first-rate museums.

Bostonians might be a brainy bunch, but they also love the great outdoors; luckily, it’s easy to get a nature fix without leaving the city. Start with the Emerald Necklace Trail, a string of six parks that stretch for seven miles. Designed by Frederick Law Olmsted (also famed for NYC’s Central Park,) Emerald Trail includes shady walkways, grassy lawns, Jamaica Pond and more. Start at the Back Bay Fens visitor centre to pick up a map of the entire conservancy. Separating Boston and Cambridge is the glittering Charles River, the place to be on a beautiful Boston day. Walk along the verdant Esplanade, or head to the water for a unique vantage point of the skyline. Sailboat lessons, stand up paddle boarding, and riverboat tours are all popular activities.

Of all Boston’s instagrammable areas, picturesque Acorn Street is perhaps the most popular. Located in Beacon Hill, the cobbled street is chock-a-block with 19th-century-row houses, gas lamps, and manicured window boxes. Yes, this is real life. Finally, let’s not allow our beloved Provincetown to slip from memory. Just 90 minutes from Boston, this alluring gay getaway offers over 40 gay guesthouses, two gay beaches, and a healthy smattering of gay bars and restaurants. It’s best if you have a weekend to escape to this tiny seaside town, but a day will do in a pinch. For the ultimate escape, discover Mr. Hudson’s ultimate gay Provincetown guide here.

Photo: Dan Gold

Of all Boston’s instagrammable areas, picturesque Acorn Street is perhaps the most popular

Photo: Jason Leung

The seasonal menu is elegant without feeling self-important, and the stunning copper bar makes a cozy place to chat over a specialty highball

Where to eat in Boston

When it comes to dining in Boston, fresh-off-the-docks seafood is where it’s at. One of the best places to indulge is Island Creek Oyster Bar, established by the famed oyster farm of the same name. Obviously, you’re going to order a plate of the oysters (it would be a crime not to); from here, you can’t go wrong with their updated take on the lobster roll or any fresh catch of the day. Then there’s Saltie Girl, a gorgeous oyster bar specializing in all things under the sea. The tinned fish options are fantastic but don’t leave without trying the crown jewel of their menu: fried lobster and waffles. If you’re feeling extra fabulous, add caviar to any dish. Saltie Girl serves up an excellent brunch, but this is the type of place that’s charming all day long.

The North End is revered for its authentic Italian cuisine, with plenty of darling options to choose from. Taking it to the next level is Taranta, an Italian-Peruvian fusion restaurant that seamlessly combines Peruvian ingredients with Italian classics. The atmosphere is quaint as can be, with three levels of exposed brick and intimate seating. In the dishes, South American staples like large-kernel corn and potatoes are expertly used to create complex flavour explosions. Taranta’s excellent service, extensive wine list, and commitment to green practices round out the experience.

Saltie Girl

No mention of the Boston restaurant scene is complete without the name Barbara Lynch, celebrity chef and recipient of Time’s 2017 “100 most influential people” award. No. 9 Park is perhaps Lynch’s most esteemed Boston restaurant, earning too many accolades to list. This is fine dining at its most polished, delivering refined Italian and French cuisine in a handsome townhouse. Then there’s Menton, also the notable work of Lynch and in many ways a return to her roots. Menton is all about modern fine dining. You’ll find creative dishes like mango vacherin with coconut, calamansi, ginger and Thai basil sorbet on the “Chef’s Whim” menu—a worthwhile splurge. Expect an extensive wine list to match the glamorous atmosphere.

New on Boston’s food scene is OAK Long Bar + Kitchen, an American brasserie specializing in farm-to-table cuisine and hand-crafted cocktails. The seasonal menu is elegant without feeling self-important, and the stunning copper bar makes a cosy place to chat over a speciality highball. Another obvious choice that showcases a commitment to regional and organic cuisine is Craigie on Main. The menu changes daily depending on what’s fresh; you can’t go wrong with chef Tony Maws seasonal tasting menu, always bursting with local flavours.

Boston Chops is a sophisticated take on the traditional steakhouse. Located in an updated, historic bank, the recently renovated space is as unique as they come. An original bank vault still stands as a hint to the restaurant’s past, while an “Instagram table” promises picture-perfect dining moments—influencer or not. Thankfully the menu lives up to the swanky decor; opt for anything from the “Rarely Celebrated” section for a drool-worthy dish. For a vibrant dining experience that is as rare as it is beautiful, Yvonne’s offers a modern interpretation of the supper club in a renovated 1862 cafe. The speakeasy-inspired restaurant delivers all the glamour of the ’20s along with delectable, shareable dishes. Reserve a table in the romantic library, all chandeliers and gold-framed artwork, or mingle at the always lively bar.

Menton | Photo: Wayne Chinnock

Shopping in Boston

Craft and Caro strives to be “the finest purveyor of gentleman’s essentials,” and their new 1,660-square-foot store does so quite well. Whether you’re searching for something for the home, work or travel, Craft and Caro has a high-quality solution. Think hand-selected items like leather goods, shaving tools, and hip flasks. Get your menswear fix at Bobby From Boston, a high-end vintage boutique in the ever-so-hip SoWa Arts District. This is not your average vintage store—the shop only features original, historical pieces in its museum-worthy displays. Even Ralph Lauren and other industry fixtures have ventured to Bobby from Boston to discover one-of-a-kind statement pieces hidden amongst the finely curated collections.

The Boston General Store offers a glimpse of yesteryear, a time when general stores were fixtures in the community and prioritized meaningful relationships with their neighbours and customers. The Boston General Store features beautiful, responsibly-made, high-quality goods that are designed to last a lifetime—a far cry from unsustainable fast fashion trends. You’ll find a little bit of everything in this attractive store, so take time to meander the displays. Then there’s Black Ink, a quirky concept shop overflowing with “unexpected necessities.” Their brand is on-point. While you never knew you needed that bento box or silk-screened greeting card, you’ll be hard pressed to leave this eccentric general shop empty-handed.

Historic Faneuil Hall Marketplace caters more to tourists than locals these days, but the iconic Freedom Trail stop remains an important Boston thing to do. Expect small boutique shops, high-end retailers, and delicious food stalls. Pick up a curious Boston trinket from one of the cart vendors, or just enjoy the live entertainment always on offer.

The Boston General Store

Photo: Tyler Springhetti

Boston Nightlife

DBar is a creative New American restaurant by day—boisterous gay bar by night. The lounge and supper club has DJ sets or events most nights of the week; if you’re around on a Tuesday, be sure to hit up their beloved Show Tune evening. Another restaurant popular for their LGBT events is the Milky Way Lounge and Bella Luna Restaurant. The name is certainly a mouthful, but this bright spot in Jamaica Plain is just the right combination of kitsch and class. The restaurant hosts at least three LGBTQ events each week, including a fiercely fun queer dance party every Friday. The obvious inclusion on any Boston gay scene guide is Club Cafe, a mainstay on the gay nightlife scene since 1982. Come on the weekends with your best dance moves, ready to join the always vibrant crowd.

The gorgeous Trophy Room is a gay bistro and bar that, as the name suggests, gives a wink to gay sports fans. There are plenty of TVs screening your favourite game, but those not interested in the teams playing can enjoy boozy craft cocktails and fun drag brunches. Guerilla Queer Bar is a gift from the Welcoming Committee, a concept party that involves an LGBT “take over” of mainstream bars and venues all over Boston. It’s not about making a statement so much as having a fabulous time outside the confines of what would typically be construed as a gay bar. The event occurs on the first Friday of each month; follow The Welcoming Committee to discover where the next glittery affair will take place.

Haley.Henry is everything we love in a wine bar. Here, wine actually takes centre stage, with an impressive selection of rare varieties from around the globe. A particular emphasis is given to small, biodynamic vineyards. A lovely selection of tapas, tinned fish, and charcuterie provide nibbles to accompany any glass but remember you’re here first and foremost for the world-class vino. The Hawthorne might be a hotel bar, but the decor and ambience claim otherwise. Designed to feel more like a cosy, upscale living room, expect mismatched furniture, elegant antiques, and contemporary art. The innovative cocktail list, created by Rob Ficks, is equally as impressive (if not more so) than space. Finally, there’s a reason why Bully Boy boasts a near-obsessive fan base. The distillery, tasting room, and cocktail bar follows a still-to-glass philosophy, bringing the best house-made tinctures and fresh, local ingredients to each cocktail on offer. Take a tour of the distillery, or simply opt to explore the plethora of handcrafted liquors via a tasting flight or expertly crafted drink. Just don’t be surprised if one of their spirits makes it into your suitcase.