Naturally, as one of the oldest cities in the country, Boston is full of history, not to mention thick accents and eclectic charm. Though it may lack a vibrant gay scene compared to other cities like Chicago, New York, or San Francisco, it’s an LGBT-friendly destination with plenty of “gayborhoods,” such as the South End and Jamaica Plain (both family friendly).
There’s a lot to do and see in the Greater Boston area—more than we could possibly include in one story. In fact, although I’ve lived in or around Boston my entire life, there’s still plenty I have yet to experience. If you’re in town for a short visit, here are some suggestions on what you shouldn’t miss.
To get an overview and bird’s eye-view of the city, you can kick off your visit with a trip to the Prudential Tower Skywalk Observatory. I recommend listening to the accompanying audio guide that will highlight Boston’s history and help you get the lay of the land. You can also sign up for an 80-minute Boston Duck Tour on an amphibious vehicle that not only hits the major landmarks but also takes you right onto the Charles River!
Of course, one of the best ways to explore Boston’s rich history is to follow the Freedom Trail, a 2.5-mile walk in the heart of the city. Marked by red bricks, the trail leads to 16 different historic sites in downtown Boston, starting at the Boston Common, and ending at Bunker Hill Monument.
The Freedom Trail
There are several ways to explore the Freedom Trail. Park rangers lead free 60-minute tours or you can take a guided tour from the non-profit Freedom Trail Foundation. You can also download an MP3 audio tour or the new Freedom Trail Official App to your smart phone. And there’s something to be said for the age-old option of grabbing a map and taking it at your own pace.
If you don’t have time to check out all of the sites, there are a few must-sees:
Boston Common and Boston Public Garden: The oldest public park in America, the Boston Common was founded in 1634 and, over the years, has been used for public punishments (don’t worry, that was in the 17th century) and as military campground for British soldiers during the Revolutionary War. Now, in the winter, you can ice skate on the frog pond, ride the carousel or have your faces painted by Millie, one of the best face-painting artists around.
After strolling through Boston Common, cross Charles Street America’s first botanical garden, the Boston Public Garden. From April to September, you can pedal a swan boat on the pond and, if you’re lucky, see the live swans that make their home here.
As you walk through the gardens, make sure to see the famous infamous ducklings featured in Robert McCloskey’s Make Way for Ducklings.
Bunker Hill Monument: The monument commemorates one of the first big battles of the Revolutionary War: The Battle of Bunker Hill. You can climb this 221-ft. tall monument (294 steps!) to get a jaw-dropping view of Boston, even if your legs hate you for the days that follow.
USS Constitution: For kids who love ships, a visit to the USS Constitution in the Boston Navy Yard is a must. Originally set afloat in 1797, Old Ironsides is an incredible display of craftsmanship. Plus, you get to feel a bit like a pirate as you explore the main deck, shaded by the billowing sails.
Faneuil Hall: A meetinghouse during the days of the Revolution, this hotspot is now a great place to grab a bite. The entire first floor is crowded with stalls selling every kind of food imaginable. Directly behind Faneuil Hall is Quincy Market—full of pushcarts, restaurants, retail stores and souvenir shops, not to mention a lot of people and some talented street performers.
Museums and Recreation
Outside of visiting the Freedom Trail, there are a multitude of cultural and recreational activities available in and around Boston, including some top-notch museums.
With tons of hands-on activities, a three-story climbing sculpture, and an outdoor maze, the Boston Children’s Museum is a great place for young children. For older kids, the Museum of Science has excellent interactive exhibits, a planetarium, and an IMAX theatre. Our daughter Addie’s favorite part of the museum is the magical Butterfly Garden.
If your kids prefer underwater life, the recently renovated New England Aquarium has everything from a coral reef center and giant ocean tank to penguins, sea dragons and seals.
The Museum of Fine Arts (MFA) and Isabella Stewart Gardner Museum are must-sees for art lovers. At the MFA, you can pick up art connection cards or a family tote from the Sharf Visitor Center for self-guided activities designed specifically for kids. Even if they aren’t fascinated by the art, it’s the perfect place for them to stretch their legs while you peruse the masterpieces.
If you’re less into the fine arts and more into, let’s say, the “physical arts,” Boston is your place. It’s home to three national sports teams: the Red Sox, Bruins and Celtics. We take great pride in our home teams.
Once the Sox broke the curse in 2004, ticket prices to Fenway Park skyrocketed. Tickets to the Bruins and Celtics, who both play in the TD Garden, are cheaper, but still can be pricey. However, if you’re a sports fanatic, there’s nothing like wolfing down a Fenway frank surrounded by Bostonians singing Neil Diamond at a Sox game.
If you’re in town on the third weekend of October, head to the banks of the Charles River and watch the Head of the Charles Regatta, the world’s largest two-day rowing regatta. In addition to locals, you’ll catch site of current and former Olympians racing down the course.
My wife, Kendra, and I have raced at the HOCR, coached crews, and been spectators. All three are amazing, but there’s nothing like enjoying the races from the shore while noshing on greasy fare from vendors lining the riverbanks.
Neighborhoods of Note
Just across the Charles River is Cambridge, a city that rivals Boston in terms of history, good eats, and tourist hotspots! You can easily drive to Cambridge, or take the subway’s Red Line. If there’s only one place you visit in Cambridge, make sure it’s Harvard Square, home to America’s oldest university and a delightful spot to explore, watch street performers, hit retail shops, and find good eats.
Walk inside the gates of Harvard Yard and discover Harvard’s beautiful campus. For kids who love science and nature, the Harvard Museum of Natural History is a gold mine of fossils, minerals, gems, and more. The Peabody Museum of Archaeology & Ethnology, connected to the Museum of Natural History, has awesome collections from central and South American ancient civilizations.
I also recommend a visit to the fun and whimsical Curious George Bookstore, located in the heart of Harvard Square. More than just a bookstore, little ones will have a blast curling up in a reading cubby with their favorite book. Just across the street, you can pick up some new books or a Harvard t-shirt at the Harvard Coop.
Another worthwhile visit would be to Jamaica Plain, one of Boston’s many unique neighborhoods. With a large lesbian population, funky shops, and lots of culture, “JP” (as it known among locals) is easily accessed by car or via the orange line subway (Forest Hills stop).
Craving the outdoors? Take a stroll around Jamaica Pond or rent a rowboat or sailboat to explore the pond. Or pack a lunch and have a picnic at the Arnold Arboretum, home to 265 acres of plant and wildlife maintained by Harvard University. You can pick up a Discovery Pack at the Hunnewell Visitor Center for more in depth exploration of the arboretum.
JP is also home to the largest zoo in New England, the Franklin Park Zoo. You can visit the giraffes, a lion, tigers, and zebras, or stop by the zoo’s Franklin Farm, which provides a taste of farm life and a petting zoo.
What comes to mind when most people think of New England food? Seafood, of course! If you haven’t yet consumed this amazing local cuisine, pay a visit to the almost 200-year old Durgin Park restaurant (next to Faneuil Hall) and fill up on fried clams and “chowda.”
Another dining option that would work for the whole family is Wagamama, a Japanese restaurant and noodle bar located at both Faneuil Hall and Harvard Square.
When hunger pangs hit in Harvard Square, head to Mr. Bartley’s Burger Cottage for one of their incredible burgers and a milkshake. Since 1960, three generations of Bartley’s have been serving up some of the best hamburgers in the country. You’ll probably have to wait in line during the summertime, but it’s worth it. They even have a kid menu, and vegetarian and gluten-free options!
There are also plenty of great places to eat in JP and we have several favorites. JP Seafood is known for its sushi. In fact, when I lived there, I ordered delivery so often they knew exactly what I was going to order.
Across the street you can indulge in incredible Indian food at Bukhara. I love the aloe chole, while Kendra and Addie prefer the chicken tikka masala.
Doyle’s Cafe, an eclectic Irish bar and restaurant, has been a part of JP since 1882. On any given day, patrons could range from local old-timers at the bar, a table of lesbians celebrating their softball win and families enjoying dinner together.
For dessert, stop in and grab a homemade ice cream at JP Licks. As the name indicates, JP Licks was founded in Jamaica Plain but now has several locations including one in JP, Harvard Square, and Boston Common. They offer ice cream safe for those who are Kosher certified, vegan, gluten-free, and even dairy-free.
Hotels in the heart of downtown Boston can be quite expensive, as they cater to business travelers as well as tourists. The Boston Park Plaza has clean, neat rooms and is walking distance to Boston Common.
Nearby, Back Bay hotels offer slightly lower prices in a location that’s still very convenient for shopping, public transportation and catching a game at Fenway Park. You might also find good weekend deals at the Hilton Boston Back Bay, Sheraton Boston and Colonnade Hotel all near the convention center.
If you have a car, consider one of the cheaper alternatives located on the Charles River in Cambridge, including the Doubletree Suites, Courtyard by Marriott, and Hyatt Regency Cambridge. While public transportation is a longer walk from these hotels, they provide great river views and easy access to the riverside hike/bike path.
Jen is a contributing writer for GayFamilyTrips.com. She lives near Boston, Massachusetts with her wife and three children. Her own blog is Adventurous Moms.
Does your family have any other Boston favorites? Share them in the Comments area below!