In Copley Square, the heart of Boston’s Back Bay neighbourhood, the 280-year-old Trinity Church can be seen reflected against the mirrored side of the ultra-modern John Hancock Tower. It’s a view that sums up a trip to Massachusetts’s capital, an exciting, on-the-pulse city with a stoic and historical backdrop. Think history books and short shorts.
Don’t be crunchy
When packing for a gaycation in Boston, you’re going to want to reconsider your cut-off jean vest, chuck the Chucks and pick up some polos. The city is far from stuffy, but it is more preppy than one may be used to. Of course, you’ll be welcome to party in your skinnies and deep vee, but don’t be surprised if you’re introduced to the charming term “crunchy,” a slang that describes the hipster-vintage uniform that so many of us love. Now don’t get it twisted: the boys may be buttoned down, but they can dance it up! Just pick the right spot and get your preppy on.
More than a tea party
It’s simple enough to hit one of the gay bars and have a good time, but to experience the hottest scene you have to be in the know. The nightlife in Boston involves an intricate understanding not only of which nights to hit certain gay bars, but also which straight bars host the best gay nights. Also, according to some locals, before 11:30pm is unspeakably uncool, but once the clubs fill around midnight, it’s a long wait in line.
Thursday nights are about the Glamlife at The Estate nightclub, a dress-coded venue that is home to sleek, stacked studs. The ground floor is a packed top-40 dancefloor, while the balcony provides a great view of the mostly 20s crowd. Fridays are all about Machine for go-go boys and dance music. Machine is an institution in gay Boston and offers a good time for most ages. Next, get blown away by Epic Saturday at The House of Blues, an enormous venue that is packed with good music and the hottest guys of the week. Standing on the third floor, looking down on the sea of glow sticks and dancing men is a near-religious experience, though it might have been the Jäger talking.
When in doubt, it’s always a safe bet to check out anything thrown by party guru Chris Harris. His monthly events are local favourites. If you’re looking for something a bit more laid-back, check out dbar in the Dorchester neighbourhood for great cocktails and a really good-looking staff.
One must be pampered after a hard weekend of partying, and Boston offers some amazing opportunities for dabbling in the fabulous life. If you must sleep, do it at the Revere Hotel. Located in the heart of the Back Bay, the Revere plies you with great service, a pillow bar, a pool with rooftop patio, and two full lines of Skoah skincare products in your bathroom.
Once rested, head on down to Newbury Street for some shopping – even if it's just window shopping. Known as Boston’s premier destination for high-end shopping, Newbury Street features Chanel, Rag & Bone, Kate Spade, Cynthia Rowley, DVF, Vera Wang and a five-storey Burberry Boutique. If you have the guts to walk in past the security guards, maybe leave the cup of coffee outside; you stain it, you bought it!
For dinner, you mustn’t miss a meal at Post 390, an urban tavern offering an incredible farm-to-post menu complete with thoughtful wine pairings. Chef Eric Brennan’s fresh, locally supplied ingredients will make you swoon and won’t totally break the bank — only slightly.
Finally, there is something you need to do that you may not be proud of. When it comes to getting a taste of the city’s history, there is really no better way than taking a Duck Tour. The Ducks take you on a trek around the streets of Boston, filling you up with fascinating tidbits, before plunging into the Charles River, where you are treated to a stunning view of the Boston skyline. Yes, they do make you quack at the occasional passerby, but in the words of our hilarious conDUCKtor Ally, “It’s not like you’ll ever see them again.” So go on, roll your eyes, and then get on that bus! It’s way better than spending your whole trip walking past buildings wondering why everyone is taking pictures.
It can be embarrassing to do the tourist thing, but it’s worth diving in if you want to experience all that this city of old and new has to offer. Do yourself a favour, throw on those practical shoes and take a walk through history before hitting the clubs. You might just learn something!
For more insight into the city and helpful travel advice, see our gay Boston city guide.
For map locations and website links to more than 160 places of interest, see our gay Boston listings pages.
More tourist info