Popular Gay-Friendly Things To Do in Boston

I stop my bike along Boston Harbor and take a deep, long inhale of the fresh sea breeze that flows off the water. Immediately, I am transported from the energetic urban life of the city to a small New England town. I look out at the view along the waterway and see historic brownstones, modern-day complexes, students hopping on and off bikes, and same-sex couples strolling alongside straight couples. The Boston of today is the culmination of nearly 400 years of breaking boundaries. From colonist revolts to LGBT rights, this city has embodied the ideals and aspirations of America since pre-America.

With Harvard’s founding in 1636, Boston quickly became a hub for American intellect and a breeding ground for the American Revolution. Famous Sons of Liberty (Whigs) and Harvard graduates like Samuel Adams planted the seeds for the eight-year war with England when, on December 16, 1773, they encouraged Boston’s residents to take part in one of the first major acts of rebellion, the Boston Tea Party. Since the American Revolution, the city has become a beacon of progressivism and has welcomed people with open arms.

This legacy of Boston as a center of progressive thought and liberal education has continued since the 17th century. With Harvard University, Boston College, Boston University, Emerson, Berklee College of Music, and dozens of other universities calling the city home, a highly educated and young population is at the center of what makes Boston unique. This is a college town on a large scale, and a traveler’s experience can change depending on whether school is in session or not. A major pull factor for many is the relative youthfulness of the city. Coeds cram pubs, spread their books at coffee shops, purchase trendy outfits at boutiques, read in the parks, and reap the benefits of a city that has been building great minds for centuries.

Boston’s highly educated and liberal population has helped the city, and state of Massachusetts, become one of the most forward-thinking in the United States. Its lesbian and gay citizens have enjoyed the right to marry since 2004, when the Supreme Judicial Court of Massachusetts ruled that denying same-sex couples that right was unconstitutional. Gay and lesbian youth are protected by one of the country’s first safe schools initiatives: the Safe Schools Program for Gay and Lesbian Students, which was instituted in 1993. The Boston area is also home to the first Gay Straight Alliance and the birthplace of the Gay, Lesbian, and Straight Education Network (GLSEN). People are also protected in the workplace, housing, and public accommodations by the nation’s second Gay Rights Bill, which was made into law in 1989.

Boston is a city built of neighborhoods. Each neighborhood has its own identity and flavor. From the heavily Italian North End to the quaint and historic Beacon Hill, understanding Boston’s physical and ethnic diversity allows visitors to appreciate what makes Boston special.

While you’ll most likely be doing quite a lot of walking in “America’s Walking City,” get your bearings first by hopping on a bike tour with Urban Adventures. These eco-friendly tours take visitors around the city and introduce you to the bike-friendly streets of Boston. Depending on your guide, you’ll get a nice mix of history and humor as you explore the different neighborhoods. You’ll also stop at most of the major city attractions, this way you can take note of the ones you may want to visit later on during your trip. History is not this tour company’s only specialty; you can even go on the ever-popular Bike and Brew Tour (don’t drink and ride, the company will take the bike back while you’re sampling artisanal beer at the local brewery).

Boston’s raison d’être is its harbor, and a visit to the city should include an exploration of this iconic waterway. If a slow ferry ride sucks the excitement out of you, book a rigid-inflatable boat (RIB) tour with Flagship Adventures, which allows you to explore the waterway at high speeds. Be sure to book early, each boat holds roughly six passengers, so tours sell out rather quickly. Departing from the Inner Harbor, near the aquarium, a knowledgeable captain guides you first through Boston Harbor, where gorgeous views of the city await, and then ventures farther into Massachusetts Harbor. Various islands are scattered about and each has a unique history and importance to the city of Boston. Activities abound on many islands like exploring a haunted Civil War fort on George’s Island to swimming on Spectacle Island. Once you’ve woven through the Boston Harbor Islands, you’ll be jonesing to discover them further.

Daily ferries take you to the islands, and in the summer, you can transform your urban vacation to an island getaway. Once considered one of the dirtiest waterways in the United States, Boston Harbor is now one of the cleanest—it only took a federal court case and some major infrastructure changes. Now, a popular summer activity is to cool off in the water. Journey to Spectacle Island where you can join in on a clambake at a Summer Shack outpost, sit on the beaches, go for a swim, and meander through the trails.

Walk along the waterfront promenade and you will also find the New England Aquarium. The main draw is the 150,000-gallon towering tank and a spiraling ramp that takes you to the top where you can watch the staff feed the rays, sharks, turtles, and other fascinating sea creatures. I escaped the crowds and found a comfortable spot to watch the ever-so-entertaining African Penguins. Avoid a trip here on the weekend, unless you love hordes of families scurrying about.

Looking for a small, romantic New England spot to call home for a weekend? Look no further than the Clarendon Square Inn. This gay-owned bed & breakfast debunks any preconceptions you may have about staying in a B&B. Modern, fresh, exciting, stylish are just some words to describe the inn’s style. You and your partner can even enjoy a rooftop hot tub with exquisite views of the city skyline.

No trip to Boston is complete without a stroll through “The Cradle of Liberty” or Faneuil Hall. Once a meeting place where the likes of Samuel Adams and James Otis gave some of their most well-known speeches, today, most tourists and Bostonians think of it mainly as a marketplace (North Market, Quincy Market, and South Market are located in the building), and it’s also home to the Boston Classical Orchestra. Stop by Boston Pretzel Bakery in Quincy Market and say hi to owner Linda DeMarco, who is also the president of Boston Pride.

It’s usually not my style when I travel to eat somewhere (or something) that I can easily get at home, but when I was walking through the lush park called the Boston Commons, I spotted a towering castle near the Boston Park Plaza Hotel and Towers. I was excited to see that it was a Smith & Wollensky restaurant. You may be able to eat at one of these high-end steakhouses in a few cities around the country, but this is the only one that offers a dining experience in a piece of history. The castle was actually an armory, built in 1882, that housed cadets until the 1960s. The restaurant group spent years and over $12 million restoring and upgrading the property, while preserving the uniqueness of the space. Dining rooms are scattered throughout the building, all with their own uniqueness—the gunroom serves as the main dining area and bar. If you’re not too busy snooping around for hidden passages, savor the steakhouse fare. With dry-aged beef done to perfection, you’ll easily leave in a food coma.