Few, if any, American cities can compete with Boston’s storied history. As the epicenter of the American Revolution, what unfolded here in the late-1700s is what makes it a fascinating place to visit. Yet the Boston of today is just as interesting as its 18th-century iteration. It’s a place that embraces contemporary art, music, and theater. Where sports fandom—the Red Sox, Patriots, Celtics and Bruins—is almost a religious phenomenon. And where seafood in all its varieties is taken as seriously as Parisians take their patisseries.
Follow us on a journey through the birthplace of modern America and enjoy your next Boston city break.
Eat
Eating your way through a city can help you understand its history, culture and vibe. It’s no different in Boston. The cobblestone streets of North End lay claim to the best and most authentic Italian food. And it doesn’t stop at pasta. Think Italian bakeries serving the sweetest cannoli, Italian capicola from salumerias, cafes that pour perfetto espresso, and pizzerias where it’s all about the crust and sauce.
The Seaport District gets its inspo from its waterside situation with an impressive array of raw bars and seafood shacks to choose from, serving lobster plucked from Maine’s waters and only the freshest oysters from nearby Cape Cod. Minutes from downtown, foodies and critics have dubbed a stretch of eateries in South End’s historic brownstones on Tremont Street “Restaurant Row.” It’s a smorgasbord of options from casual jazz cafes to fine dining establishments—feast on sole meunière at French bistros or posh lobster mac & cheese at American brasseries.
If choosing a single restaurant proves impossible, head to Faneuil Hall Marketplace and Quincy Market Food Colonnade for all of Boston’s signature food options under one roof. Gifted to the city in 1742 by a prosperous merchant, Faneuil Hall brought together farmers and fishers. Today, it remains a vibrant central meeting place in Boston, with dozens of shops, restaurants, bars, pubs, and pushcarts.
When you eventually decide on a cup of classic and creamy clam chowder from a kiosk or opt to sit down to shuck oysters on the half-shell, be sure to finish things up with a slice of Boston Cream Pie. This tantalizingly sweet and buttery vanilla cake is filled with custard and topped with chocolate ganache. Tummies full, stay awhile to absorb the cheery atmosphere. Musicians pitched up at Faneuil Hall in the 1970s to entertain the construction workers who were tasked with the urban renewal of the Marketplace. Their presence proved so popular, they never left. Jugglers and acrobats have joined the ranks and made Faneuil Hall synonymous with impressive street performances.
Play
If you’re not in Boston for the food, sport, shopping, or family-friendly attractions, chances are it’s the city’s remarkable history that’s enticed you. As the key location in the American Revolution, Boston is a more storied city than many others in the U.S. and why many visitors to Boston start with walking the famous Freedom Trail. But even if you’re not enraptured by the city’s tales of yesteryear, the Freedom Trail is a great way to get your bearings in this highly walkable city.
Boston Common and Boston Public Garden
The Freedom Trail starts at the city’s crowning green space and city epicenter: Boston Common. Before setting off on the Trail too hastily, first take a leisurely stroll around America’s oldest public park. Founded in 1634, it’s a place that was designed to draw Boston visitors and locals together and still does to this day.
Adjacent to the Common is Boston Public Garden, a botanical garden created for the city’s Victorian residents to promenade and admire exotic and colorful plants. The famous swan boats on the lagoon have bobbed on the water since 1877, and the sweet “Make Way for Ducklings” sculpture serves to enchant visitors as they wander along the old Boston cobblestones through the Garden.
In summer, families sail model boats on Frog Pond and ride the traditional carousel while city workers order quick bites at a food truck in Brewer Fountain Plaza before retreating to the highrises that surround the park. Summertime also brings a programme of alfresco piano recitals by students from Berklee College of Music – grab a coffee and find a spot to relax and enjoy the music.
If you’re visiting in the winter months, Boston Common is idyllic when Frog Pond becomes an ice rink and creates a magical and Christmassy atmosphere. You can hire skates for a quick lap or two or take a lesson if you feel like refining your technique. Post-skate, wrap your hands around a warming cup of creamy hot chocolate from the seasonal Frog Pond Cafe.
The Freedom Trail
First-time visitors to Boston should follow the well-marked, 2.5-mile Freedom Trail. It’s a route that connects 16 important landmarks and charts the story of the American Revolution and beyond through a collection of meeting houses, burying grounds, museums, parks, and ships. Choose an enthusiastic costumed guide to whisk you back to the era on a full-works tour if you want the whole Freedom Trail shebang. Otherwise, grab a map and self-guide for free. That way, you can dip into the sites that pique your interest and veer off course when you spot other locations to explore.
An unmissable stop on the Freedom Trail is the USS Constitution in Charlestown Navy Yard. This famous warship, nicknamed Old Ironsides was launched in 1797, making it the oldest commissioned warship afloat anywhere in the world. It’s worthy of proper exploration, so set aside a couple of hours if you can. Step aboard the ship for a guided tour, then visit the accompanying USS Constitution Museum with interactive exhibits that bring tales of the ship’s history and people to life. There’s the chance to try furling a sail and firing a cannon to experience life as a sailor.
Another notable highlight on the Freedom Trail is the Old State House. It’s the oldest surviving public building in Boston and was once the epicenter of Boston’s civic, business, and political life. Period rooms are chock full of exhibits and Revolution-era objects to help tell the stories of what happened here. There are occasional live performances for an immersive experience of the time and guides available who are keen to share their enthusiasm and knowledge.
Boston Tea Party Ships & Museum
The most notable historic location away from the Freedom Trail is where the replica Boston Tea Party Ships are moored at Griffin’s Wharf. It’s a handily central location which is easily reachable from the Downtown and Waterfront neighborhoods.
The Boston Tea Party set the US on a new course in 1773. The event was named after chests of tea were thrown into the water from ships as a protest by a group of patriots led by Samuel Adams. Their actions ultimately led to the American Revolution. The events that unfolded are brilliantly told at the Boston Tea Party Ships & Museum at the exact location of the protest.
Events spring to life with the help of two replica ships and interactive museum exhibits. Walk the decks of the Brig Beaver and Eleanor – the two replica Tea Party ships, throw tea overboard as part of the hands-on experience, and witness a reenactment of a lively debate between the patriots and loyalists. The only known surviving tea chest from the Boston Tea Party is the Robinson Tea Chest, a significant artifact which has been lovingly preserved and displayed in the museum. You’ll emerge from this attraction informed and entertained in equal parts.
Boston Harborwalk
While there’s plenty in the city for history buffs, if you’re more in the mood to experience 21st century Boston, choose a section of the Harborwalk to explore. This 43-mile walkway weaves around eight neighborhoods to discover a more behind-the-scenes version of Boston. It winds through central locations then heads away from well-worn tourist trails and into local communities. En route, explore public beaches or hop on a water taxi to whisk yourself away to another part of the city.
If you’re traveling with children, plan to start or finish exploring the Harborwalk around the Waterfront neighborhood. The Christopher Columbus Waterfront Park, a pretty city park near the Faneuil Hall Marketplace, is a good starting point. Follow with a visit to the impressive New England Aquarium before rejoining the Harborwalk for a 15-minute walk to the Boston’s Children’s Museum – one of the best kids’ museums in the world. It’s aimed at children 11 and under and features play-based and educational exhibits over three floors. Older kids might get more out of the interactive Museum of Science, complete with IMAX films, planetarium shows, and live presentations just off the Harborwalk in the North End neighborhood.
Some of Boston’s well-known attractions are along the Fort Point and Downtown sections of the Harborwalk, including the dynamic Institute of Contemporary Art with its sensational visual art exhibitions and diverse performances. The building is almost as impressive as what lies inside – it’s a glassy creation cantilevered over the waterside plaza.
Fenway Park and Boston sports
Sport is woven into the fabric of Boston and coordinating a visit to the city around a Red Sox home fixture is never a bad decision. It’s a warm-weather sport and the regular Major League Baseball season typically runs from late March to early October. Arrive early, grab an obligatory hot dog and some Red Sox merch, and cheer on the team. Games can last up to three hours or more, but there are plenty of concession stands to keep fuelled up.
Can’t bag a ticket? Drop into the bars and restaurants in the Fenway-Kenmore neighborhood to experience the buzz that awakens every time the team grace the hallowed Fenway Park. Or, for a closer look at the stadium, take a behind-the-scenes tour of this legendary ballpark. There’s a quickfire 15-minute option if you’re pushed for time, but the hour-long guided tour will reveal more about the original 1912 scoreboard known as the Green Monster and the Red Seat that is said to mark the longest home run ever hit at Fenway Park.
Bostonians’ love of sports doesn’t stop at baseball. The Patriots, the Celtics, and the Bruins are well-supported teams across football, basketball, and hockey. It’s worth getting tickets to join in the jovialities with a glass of locally brewed IPA.
Newbury Street and Prudential Center
Boston is the ideal shopping break destination because the central shopping hub is both neatly compact and utterly charming. Pretty Newbury Street in the Back Bay neighborhood is an upscale retail area mere steps away from Boston Public Garden. High street and designer stores are interspersed with art galleries for those who enjoy a little culture alongside their shopping fix. It’s easy to spend a day wandering the length of Newbury Street, with plenty of cafes and restaurants standing by for caffeine pit stops and lazy lunches.
If you’re in Boston in the winter and the weather is particularly chilly or snowy (temperatures can sit stubbornly below freezing in winter here), seek refuge in the neighboring mall, the Prudential Center. There are shops, vast department stores, and high-end eateries if shopping, mooching, and dining are part of your perfect Boston city break.
Stay
The fun-loving Moxy Boston Downtown is in a central location in the Theater District, a couple of blocks from Boston Common. It’s the kind of place that invites the party in, with Bar Moxy constantly proving a lively place to start or finish a night out with playfulness encouraged in the photo booth. That said, rooms are calm enclaves, all cool steel and dove grey with pops of Moxy’s hot pink brand styling. Floor-to-ceiling windows frame views of the city and flood the rooms with light.
If you’ve got your sights set on a waterfront hotel, consider The Envoy in the Seaport District. The harbor views are fantastic, particularly from the Lookout Rooftop bar, where you can order a cocktail and find a spot around a warming fire pit. Rooms are super posh and have unobstructed, gorgeous water views.
