Part of the Gay Boston Guide — bars, events & things to do.
Boston, Massachusetts
Playful boutique hotel in Boston's queer-friendly South End.
A vibrant boutique nestled in the charming South End, Staypineapple blends playful design with community spirit. Rooms feature pillow-top beds and colorful accents; the hotel is pet-friendly and offers bike rentals for exploring. Guests praise the welcoming staff and proximity to queer-friendly brunch spots and cafés. For travelers seeking neighborhood authenticity with a whimsical twist, it's a joyful essence of local LGBTQ+ life.
Have feedback on this description? Let us knowGet the full experience — check in, follow this venue, and connect with the community.
No upcoming events
Try checking a later date or browse events in the app
Catch your city's vibe or the global LGBTQ+ scene.
No spam, unsubscribe anytime.
From the first state to legalize same-sex marriage to a walkable gayborhood in the South End, here's your insider guide to queer Boston.
June is Pride Month, and the chaos is real. Here are 25+ of the best gay events in June 2026 across North America, organized by week so you can actually plan your travel.
Your complete guide to every dedicated lesbian and sapphic bar currently operating in the US, mapped by city, with what makes each one worth the trip.
The gayest cities in America, ranked by the Out x Out Gay City Score — the most gay-friendly places for nightlife, safety, community, events, and more, with the top gay bars in each.
$550
Experiences powered by Viator
