Category Archives: Gay

I’ve often commented on how much I love Boston and am happy to act as any newcomer’s or visitor’s concierge, answering questions or providing suggestions. While I realize my preferences may not be yours, I thought I’d share ideas on what to see over three days in Boston. I’ve taken care to avoid suggesting places only a trust fund baby can afford. You can read my suggestions from Day 1 Here and Day 2 Here.

Day 3:  Three (Gay) Days in Boston

What would a visit to Boston be without checking the Freedom Trail? This 2.5 mile walk chronicle’s America’s history in the years leading up to and during the American Revolution. Although the walk technically starts on Boston Common, I’d suggest starting your morning by splurging at The Omni Parker House dining room for breakfast just a few blocks from the start of the trail. This restaurant has been serving Boston and Boston travelers since 1855 and is the birthplace of the Boston Cream Pie. It also has the distinction of having employed Ho Chi Minh and Malcolm X.

After walking the Freedom Trail you are going to be tired so spend the afternoon taking a 90-minute Duck Tour.  Before or after your tour (you decide) grab lunch on Boylston Street in the Back Bay. I’m partial to the patio of Atlantic Fish Co. if you’re not a fan of seafood or want a cheap eats alternative check out Cafe Jaffa a few blocks away.

Start your final evening by visiting another iconic Boston restaurant, The Oak Long Bar + Kitchen, in the Fairmont Copley Hotel in Copley Square. For dinner on the cheap head over to a South End neighborhood mainstay, Anchovies, for basic, affordable homestyle Italian-American that is just a few blocks away. For something a little more interesting, try Myers + Chang – a Pan-Asian Tapas restaurant on Washington & Berkeley Street.  Take a taxi rather than walk – it should be about $6 from Copley; again make reservations. After dinner walk just two blocks down Washington Street to Boston’s newest gay bar – more of a Bear / Sports Bar – Cathedral Station.

I’ve often commented on how much I love Boston and am happy to act as any newcomer’s or visitor’s concierge, answering questions or providing suggestions. While I realize my preferences may not be yours, I thought I’d share ideas on what to see over three days in Boston. I’ve taken care to avoid suggesting places only a trust fund baby can afford.  You can read my suggestions from Day 1 Here.

Day 2:  Three (Gay) Days in Boston

Leave all the walking for the afternoon today and start your morning at the original The South End Buttery on the corner of Shawmut Ave and Union Park St. Relax and enjoy the morning hub bub, use the free wifi and people watch at this busy corner coffee shop that serves some of the best coffee in town.

In the afternoon head over to Neptune Oyster at 63 Salem Street and treat yourself to their lobster roll; it is expensive but worth it. And unlike at dinner, seats are relatively easy to get at lunch. Then go to the recently expanded The Modern Pastry to get something decadently sweet you can enjoy while you stroll down The Rose Kennedy Greenway, which offers views of Boston’s skyline, harbor and public art. When you end your walk near Chinatown, take a left and head over to Boston’s only remaining Gay Bookstore, Calamus Bookstore (at 92b South Street; open 11am – 7pm Tues – Sat and 12-6pm Sun). Peruse the shelves and support this great LGBT bookstore with a purchase or two.

In the evening go to Sister Sorel on Tremont Street (or next door if it is nice weather – Tremont 647) in the South End to carouse with locals. Skip the food here; it is the n’hood vibe that makes the place fun. While it isn’t technically a gay pub, there is always a quorum present. When you get hungry head over to Stella on Washington Street; it may seem like a tough area but it is safer than you’d ever imagine so walk like a local down W. Brookline Street until you arrive at Stella. If it is the weekend, ask for directions to the back bar where it is easier to snag a seat.   After dinner head to the front bar for drinks and people watching.