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These are all compelling reasons to add Boston to your travel list if you want to delve into the roots of the U.S. and experience genuine Boston hospitality. 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.
There aren’t any specific cruising bars either. This hotel epitomizes that with its stylish and contemporary interior.
Gay Map of
The GayMapper interactive gay map of Boston, Massachusetts helps you locate all the gay bars, gay clubs, gay events and gay cruising spots.
Dates: 4 – 5 July, 2026.
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. Summers, on the other hand, are warm but not unbearable, making it the best time to come for those interested in watersports and outdoor activities.
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. 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.
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. 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.
Gay Tours in Boston
6. 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. 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.
The university's red-brick buildings, ivy-covered walls, and historic landmarks like Widener Library and Memorial Hall provide a picturesque setting. The march through Boston is followed by a vigil and speeches. 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.
Airport Transfer and Transportation
3. Day Trips from Boston
General Tips
Boston is a great city to visit any time of the year, but their winters are cold—brutally cold!