On Massachusetts Bay, Boston is known for its fresh seafood. Credit: Shutterstock

Boston: A City Guide

History-loving, sports-mad, seafood-chomping Boston. This maritime city in Massachusetts will steal your heart

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. 

Boston

Play

First-time visitors to Boston should follow the well-marked, 2.5-mile Freedom Trail, a whistle-stop tour around 16 landmarks that chart the story of the American Revolution and beyond. Want the whole shebang? Choose an enthusiastic costumed guide to whisk you back to the era on a full-works tour. Otherwise, grab a map and self-guide for free.

The Freedom Trail starts at the city’s crowning green space, Boston Common. Before setting off too hastily, take a stroll around America’s oldest public park first. In summer, you’ll see families sailing model boats on Frog Pond and riding the carousel while city workers order quick bites at a food truck in Brewer Fountain Plaza and enjoy an alfresco piano recital by a student from Berklee College of Music. Boston Common is just as idyllic in winter when Frog Pond becomes an ice rink that creates a magical atmosphere. 

Adjacent to the Common is Boston Public Garden, a botanical garden created for 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.

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 neighbourhoods for a more behind-the-scenes version of Boston. En route, explore public beaches or hop on a water taxi to whisk yourself away to another part of the city. 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 stunning visual art exhibitions and diverse performances.

Sport is woven into the fabric of Boston, and coordinating a visit around a Red Sox home game is never a bad decision. Drop into the bars and restaurants in the Fenway-Kenmore neighborhood to experience the buzz that awakens every time the city’s beloved team graces hallowed Fenway Park. Bostonians’ love of sports doesn’t stop at baseball. The Patriots, the Celtics, and the Bruins are all well-supported teams across football, basketball, and hockey, respectively, and are worth bagging tickets to join in the jovialities with a glass of locally crafted IPA.

Stay

Moxy Boston Downtown

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. 

Boston

The Envoy Hotel

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.