By Melanie Carden
May 2024
Thanks to its outsized role in America’s history and iconic sports scene, visitors to this city are sure to take home the ultimate souvenir—a bit of Boston swagger
Your essential guide to the best things to see and do in Boston, MA. Find more travel inspiration for more amazing cities here
Boston is a place where coastal beauty comes with a hint of New England saltiness. The city made it known, in December 1773, that it wouldn’t take guff from anyone—certainly not Britain and its taxation without representation—when its citizens tossed 342 crates of tea into the harbor, launching the colonies’ fight for independence.
That tea-tossing determination lends itself to the city’s small-but-mighty persona, dense with top universities, art, innovation, culture, and its storied sports culture. From the Red Sox’s legacy of grit and glory to Bostonians’ can-do attitude, the city’s universal appeal is hidden in plain sight.
Take a ride on the Boston Commuter Ferry
The Old State House dates back to 1713
Art is ever-present in Boston—from time-honored institutions like the Museum of Fine Arts Boston to Dorchester Brewing Company’s beloved Museum of Bad Art. Then there’s the enchanting grounds of Fenway’s Isabella Stewart Gardner Museum, the site of the world’s largest—still unsolved—art heist. See works by the likes of John Singer Sargent, which compete for visitors’ attention when the kaleidoscope of blossoms make their annual debut in the open-air courtyard.
The Isabella Stewart Gardner Museum’s leafy courtyard
Visit Boston Center for the Arts for what’s hot right now—performances and works packing cultural punch—and leave time for screenings and exhibits at Chinatown’s Pao Arts Center and the always-free Harvard Arts Museums.
Beacon Hill also boasts galleries and architectural eye-candy, with swoony brownstones, the quirky trompe-l’oeil Scarlett O’Hara House, and the immersive architecture of The Liberty Hotel—where folks sip craft cocktails in the what was once Charles Street Jail’s old “drunk tank,” now Alibi.
In terms of architecture, the city’s profile includes everything from 18th- and 19th-century Federalist structures to sleek, contemporary skyscrapers. Be sure to add the 1806 African Meeting House to your architecture checklist (find it on the Black Heritage Trail), as well as key stops on Boston’s Freedom Trail, including the Georgian King’s Chapel (1754) and the Old North Church of Paul Revere fame. Additionally, visit the breathtaking Central Library at Boston Public Library, and the city’s oldest public building, the Old State House.
And don’t miss the North End’s Spite House, an architectural manifestation of sibling squabbles, Boston-style. The legend goes that when two Civil War-era brothers inherited the land, one built a house on it without the other knowing—in retaliation, the second brother built a very skinny, very inconvenient house on the rest of the land to block entry.
Logan International Airport (BOS) is the main airport. Manchester-Boston Regional Airport (MHT) and Worcester Regional Airport (ORH) are both one hour away. A water taxi from Logan International Airport travels downtown in 10–15 minutes, with beautiful views along the way. Arrive by Amtrak train from Albany, Providence, Philadelphia, New York, and Washington, D.C.
Snowstorms can arise as early as November and as late as mid-spring. Pack warm and waterproof layers.
Buy either a 1-Day or 7-Day LinkPass for unlimited rides on the subway, known as “the T.” Children aged 11 and under ride free.
Most of the subway is accessible without assistance, excluding some of the Green Line and one Blue Line station due to gaps between train cars and platforms.
Wheelchair users traveling on the Green Line should wait at the front of trains to receive ramp assistance from operators. Boston’s MTBA train stations are fitted with braille signs to help the visually impaired navigate.
Massachusetts was the first state in the nation to legalize same-sex marriage and remains progressive today. The Boston Pride for the People parade and festival takes place in June at Boston Common and City Hall Plaza.
Boston’s varied playgrounds await, from lush parks like Boston Common and the Public Garden to the many museums. The Duck Boat Tours are more educational than the name suggests, exploring the city by land and water. Combine a visit to the New England Aquarium with a ferry from Long Wharf to Charlestown Navy Yard to play sailor on the U.S.S. Constitution for free and visit its low-cost museum. The Boston Children’s Museum offers $1 Sunday admission, and there’s never a charge to visit The Boston Fire Museum. Seaport’s ageless outdoor romp-zone, The Lawn on D, offers giant Jenga and supersize swings, but leave time for Mapparium and walk through the heart of a three-story globe.
Boston is known for oysters, and for good reason
The city’s North End is a cozy, predominantly Italian enclave where handmade pasta and gelato reign. Savor the braised short-rib ravioli at Prezza, and grab cannoli from Mike’s Pastry, boxed and tied with their signature twine. Meanwhile, in Boston’s South End, James Beard Award-winning chef Ken Oringer’s Coppa enoteca serves up from-scratch Italian goodness and sublime monthly gluten-free nights.
Visit the nation’s oldest continously serving restaurant, Union Oyster House, for the city’s famous chowder, or take your meal sky-high at fine dining options like Contessa, or Michelin-starred chef George Mendez’s Portuguese-infused cuisine at Amar. Those in the know can be found sipping craft cocktails at The Wig Shop, eating tapas at Boqueria, or taking respite in the narrow alley of Casa Romero with its award-winning margaritas.
Back Bay’s Newbury Street deserves its spotlight, offering luxury storefronts like Chanel, but a few blocks west of the Public Garden, many shops are edgier and locally owned. Other iconic shopping spots include Faneuil Hall Marketplace, built in 1742. Though the vendors have changed, the vibrant hum remains as pushcart vendors chat up visitors and fishmongers tout their daily catch.
Then there’s SoWa Boston—the soulful art and design haven in the South End. Lose a few hours here digging through new and reclaimed art, high-end craftsmanship, boutiques, and vintage markets. Or dabble in Boston’s thriving bookstore scene, anchored by historic Brattle Book Shop (think antiquarian tomes and alleyway sale racks). Independent and pop-up bookstores seem to sprout up weekly, like the inclusive romance bookshop Read My Lips or the cozy Beacon Hill Books & Café.
Faneuil Hall Marketplace is a foodie mecca
For some, traveling to Boston is a pilgrimage to the oldest ballpark in Major League Baseball. When Fenway Park opened in 1912, then-owner John I. Taylor put up a high-for-the-time fence to prevent anyone from watching games for free. Over the years, the wall—dubbed the Green Monster—grew in fame, and in 2003 seats were introduced allowing fans to watch the game from its peak. Below, the park’s hand-operated scoreboard is still in use. What’s more, there’s a large window where The Bleacher Bar patrons can watch warm-ups without a game ticket. Take a tour of Fenway Park and even get a glimpse of Fenway Farms, the park’s rooftop garden, which produces up to 6,000 pounds of fragrant herbs and produce per year.
Elsewhere, sports enthusiasts can catch a Celtics or Bruins game at TD Garden; or get in on the action by visiting the Seaport’s funky electronic darts venue, Flight Club, or ping-pong bar, SPIN.
Childhood friends turned actor-producers Matt Damon and Ben Affleck made their names in the film industry in 1997 when they premiered Good Will Hunting—set in their hometown, Boston. Their characters’ favorite bar, Southie’s L Street Tavern, still welcomes locals and visitors alike. Find the Boston Public Garden bench where Robin Williams delivered his Oscar-winning monologue to Damon. Meanwhile, The Departed and Spotlight are standouts, together with long-running series Cheers, which ended in 1993 but still draws fans to the Beacon Hill bar that inspired it.
Many Boston hotels are concentrated in the Downtown area. Downtown provides easy access to the North End, Theater District, West End—including TD Garden—and the Seaport District’s breweries, waterfront dining, and spirited nightlife. Popular Boston spots like Faneuil Hall Marketplace, Boston Public Market, and many Freedom Trail sites are Downtown, with abundant transit stops.
The Back Bay, southwest of Downtown, allows for a short walk to Newbury Street’s famed shopping, the Charles River Esplanade, Trinity Church, and the city skyline experience, View Boston. From the Back Bay, visitors can easily pop over to Beacon Hill, Fenway Park and its bustling Lansdowne Street, and the South End.
Melanie Carden is a Boston-based travel writer and former chef focusing on food, culture, and immersive adventure. Her work has appeared in Thrillist, Business Insider, Paste Magazine, The Gay & Lesbian Review, and Film Fest Magazine.