Historic Boston makes for a perfect weekend. The city is so walkable (and has such great public transit), you will have sore legs. The historic city is home to more than five universities, so it feels like being in a college town on steroids.
Massachusetts is a civil rights and gay rights pioneer. Massachusetts celebrates 20 years of legal gay marriage, Governor Maura Healey was the first elected lesbian Governor in the nation, and Boston Mayor Michelle Wu is the city’s first Chinese mayor.
Although Boston has just a few bars, fabulous Provincetown is just a ferry ride away with its lively nightlife scene.
Luckily, the Club Café Bistro and Video Bar is always hopping and has several events every night of the week. It also has not one but two cabarets, great dining, dancing, drag brunches, and more. It was founded in 1983 as a video bar and is still going strong!
What to Do
Learn about the history of this city by taking a Boston by Foot Walking Tour. I took the history walk (aka Heart of the Freedom Trail Walk) which met in front of Faneuil Hall by the statute of Samuel Adams. A guide tells you the history of Boston and how our country came to be thanks to the independent and freedom-minded people that galvanized all the colonies to rebel against the British and form the U.S. You will learn the correct version of history, too; did you know that only five people were shot in the “Boston Massacre”?
Nearby Faneuil Hall is the Old State House, the oldest surviving government building of the old British Colonies which was built in 1713. It also served as the birthplace of the independent government of Massachusetts.
Make your first stop the Boston Public Library in Copley Square. You will find it at 700 Boylston Street. It’s more of a museum that’s used as library. Don’t miss the murals, especially those on the third floor. The murals surrounding staircase hall are the only mural work outside of France done by Pierre Puvis de Chavannes, a French painter who was considered one of the greatest muralists of the 19th century.
Other must-visits are Boston Common and Boston Public Garden, which are two great parks in the middle of the city. Then follow the 2.5-mile self-guided Freedom Trail with 17 revolutionary landmarks.
Take the Green Line subway out to the Isabella Stewart Gardner Museum near Northeastern University. This quirky museum has a plant-filled courtyard and more. Enjoy the Raquib Shaw: Ballads of East and West. Nearby is the Museum of Fine Arts, and of course, Fenway Park.
Where to Eat
I had dinner at the Boston Chops Urban Steakhouse Downtown which was great. If you don’t like steaks, try the salmon. You can even sit in an old bank vault!
Don’t miss the fast-casual Eataly in the Prudential Center. Filled with Italian specialties, it also offers fast casual dining featuring everything Italian. You can’t beat their pizza, but they also have salads and more. Take home some gourmet pasta sauce or Italian cheese and wine.
The food hall behind Faneuil Hall (Liberty Market) has every type of Boston specialty dish you could imagine. I had a fresh carrot juice and salad while others enjoyed lobster bisque in a bread bowl. The seafood in Boston is fresh and local – indeed, it was one of the city’s first industries that supplied cod to Europe back in the day.
Boston Nightlife
I loved the Club Café Bistro and Video Bar. Located in the Back Bay neighborhood at 209 Columbus Avenue, this was a fun multi-purpose bar. They had two cabaret shows the Saturday night I was there. Plus they serve food, so dining is an option. There is something going on every night, including drag brunches, karaoke, and more. Founded as a video bar in 1983, it has survived the retraction of bars in the city which some blame on gentrification while others note it is a nationwide trend. Other bars in Boston include Jacque’s Cabaret, a drag bar; Cathedral Station, a sports bar; and The Alley Bar in downtown.
Where to Stay
I stayed at the Altoft Boston Seaport at 401 D Street. The modern, new hotel has a Brazilian steakhouse in the building and a fun WXYZ Bar. Nearby is a liquor store and a Dunkin Donuts. South Boston is just a half mile south , which also has restaurant and retail options such as the Foodie’s Market at 230 West Broadway (which has a hot food and salad bar) and you can take the #9 bus into Back Bay. Best of all, the Aloft is a value and has no annoying “resort fee.” (Sadly, many Boston hotels now tack on $35 dollars a day or more for a fee which is sometimes called an amenity, destination, or resort fee. I don’t pay junk fees especially where they are buried as a footnote as “taxes and fees” on third-party booking sites.)
Other Helpful iInts
Getting around on the five subway lines or the bus system, known as the T, is a breeze.
South Boston is a different neighborhood from the South End. It’s confusing.
Boston is a city of neighborhoods. Both South Boston and the South End are great, as are Back Bay and Copley Square.
Spirit Magazine is Boston’s LGBTQ publication.
Plan your trip and learn more about Boston here.
Bill Malcolm is a syndicated travel writer whose column appears in publications and on websites throughout North America and on the travel blog at iglta.org.