Gay Boston Boston City Guide City Guides > United States > Gay Boston Boston Casey SiemaskoBoasting 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. Feel like getting away? Take a trip planned just for you, and let us do all the work. Discover Trip Design Hotels Things to do Things to see Food & Drink Shopping Nightlife Trip Design Where to stay in BostonFor 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 BostonThank you for reading Mr Hudson.Subscribe to City Guides or log in to continue reading. Subscribe now Log inSpecial SelectionExclusive Mr Hudson offersOut now from gestaltenMr Hudson Explores Browse the Book Explore more The Surfjack Hotel & Swim Club - paying homage to the true soul of WaikikiForget tiki kitsch; the Surfjack in Waikiki succeeds in seamlessly blending nostalgic surf culture with modern and fresh Honolulu design. Read story > The best places for stargazing in the USWe’re lifting our eyes to the skies to discover the best places for stargazing across the US, where there’s nothing manmade to ruin our view of Mercury in retrograde. Read story > The world's best wine hotelsWhether a rich Rioja by the fireside or a crisp chardonnay on the seafront, it doesn’t matter where, when or what season, wine is always our go-to. Enjoy the best and most coveted wines, moments from the vineyards they were bottled. Read story > Subscribe to our newsletterYou can unsubscribe at any time by clicking the link in the footer of our emails. We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing. Sign up for exclusive insider promotions SIGN UPBe the first to receive exclusive luxury travel offers and special promotions by subscribing to our newsletter.