Even then, you’ll find rainbow flags billowing throughout the town. That said, the main gay areas of Boston are the neighborhoods of Jamaica Plans and the South End, where the gay community has been since the 1980s. What’s more, there are many gay hotels in Boston with an extremely warm and friendly staff who more than welcome LGBTQ travelers.īesides Boston Gay Pride, there are many gay bars and clubs peppered throughout the city. In fact, Massachusetts was the first state to allow gay marriage in America, which makes Boston a leader in LGBTQ destinations with a visible gay scene. Boston might take pride in its roots, but it hasn’t lost sight of its trailblazing and revolutionary ways, especially when it comes to the LGBTQ community. A walkable downtown and museums, buildings, and parks with time-honored stories to tell are what makes Boston so special. Boasting more than four centuries of rich cultural heritage, Boston could very well be America’s oldest city.