Tag 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.

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.

I’m happy to provide suggestions on places to stay but for the purpose of this series of posts I am going to assume you have reserved a hotel, B&B or apartment in downtown Boston and will provide suggestions with dining options for morning, afternoon and evening.

Day 1:  Three (Gay) Days in Boston

Start your morning at Panificio Bakery on Charles Street in Beacon Hill. Grab a cup of coffee, tea or juice and a decadent, warm carb recently pulled from the oven that you can enjoy while walking along the Charles River. This public park offers great views of Back Bay, Cambridge (and men walking, running and biking).

In the afternoon, enjoy a relaxing picnic in Boston’s Public Garden (the nation’s first botanical garden). Call The Upper Crust in Beacon Hill  (617) 723-9600 and ask them to walk or bike over your pizza order. All you need to have is a cell phone and a credit card. They will bring the pizza, drinks, plates and napkins. You can enjoy the park, the views and of course the pizza.  After lunch take a stroll through Back Bay: enjoy the Commonwealth Mall with sculptures on each block with some of the neighborhoods most beautiful homes or walk along Newbury Street (Boston’s version of 5th Avenue) which includes both national luxury chains as well as one of a kind boutiques.

In the evening head over to The Trophy Room on the corner of Berkeley and Chandler Street in the South End. Grab a cocktail (or two) at this gay friendly neighborhood bar and when your appetite reminds you it is time to eat, walk the four blocks to Aquitaine on Tremont Street (reservations are strongly suggested). I won’t presume to know your preferences and am confident that everything on the menu would be to your liking. After dinner if you are in the mood for a 20 or 30-something crowd head to Club Cafe on Columbus Ave and Berkeley Street where there is always a crowd and dancing in the backroom. If you would like something more relaxing walk two blocks down Union Park to Boston Chops and enjoy a cocktail and the guys who congregate here after dinner by the bar.