In some Boston neighborhoods, you can't walk a step over the cobblestone streets without running into a historic site on the Freedom Trail.
In others, there aren't many traditional things to see, but there are plenty of eating and entertainment options. Some places, such as West End, might not draw the tourist crowds for sightseeing, but offer convenient and relatively affordable places to stay. From Downtown to Beacon Hill, this guide to Boston's best neighborhoods can help you plan the perfect trip.
Downtown and the Waterfront
Best area for first-time visitors
Downtown and the Waterfront, which includes the Financial District, is basically tourist central, and with good reason. With the sun sparkling off the water and the boats bobbing at their moorings, it's hard to resist this city by the sea. Almost every visitor will traipse through Downtown while following the Freedom Trail to Faneuil Hall and Quincy Market (one of the most visited tourist sites in the country). Stroll across the Rose Kennedy Greenway parks to the harbor. From Long Wharf, you can catch the ferry out to the Boston Harbor Islands or a whale-watching cruise to Stellwagen Bank. Visit the nearby New England Aquarium, and make the most of the seafood restaurants and outdoor cafes that line the shore.
Kenmore Square and Fenway
Best neighborhood for nightlife
Kenmore Square is the epicenter of student life in Boston. In addition to the Boston University (BU) behemoth, there are more than a half dozen colleges in the area, and a disproportionate share of nightlife and inexpensive places to eat as a result drawing club-goers and budget travelers. Baseball fans flock to the streets surrounding Fenway Park. At the other end of the neighborhood, culture-vultures go to the artistic institutions along the Avenue of the Arts (Huntington Avenue), including the Museum of Fine Arts and Symphony Hall. Art lovers should devote a day to exploring one of these celebrated art venues (although deciding which one will be a challenge).
South End and SoWa
Best neighborhood for art lovers
Once downtrodden, the South End was claimed and cleaned up by the LGBTIQ+ community, and now everyone wants to live there. And why not? The neighborhood boasts the country's largest concentration of Victorian row houses, and the city's most innovative and exciting options for dining out. SoWa – the area south of Washington St – was once a barren area. The artistic community moved in and converted old warehouses into studios and galleries. This neighborhood is now home to Boston’s edgiest, up-and-coming art scene, and hosts weekly markets including SoWa Open Market and SoWa Farmers Market.
Chinatown and the Theater District
Best place for a pretheater meal and a show
Although tiny by New York standards, Boston's Theater District has long served as a pre-Broadway staging area. Many landmark theaters have received face-lifts in recent years, and their colorful marquees and posh patrons make for a festive night out on the town. The Theater District is also Boston's club hub. Nearby, Chinatown is overflowing with restaurants, live-poultry and fresh-produce markets, teahouses and textile shops. As well as the Chinese, this tight-knit community also includes Cambodians, Vietnamese and Laotians. Chinatown is a popular stop for lunch, a pretheater dinner or a postclubbing munch. East of Chinatown, the Leather District is a pocket of uniform brick buildings that also shelters some fine restaurants.
North End
Best neighborhood for restaurants
The North End feels like an Old World enclave. Italian immigrants and their descendants have held court in this warren of narrow streets and alleys since the 1920s. The neighborhood's main streets are packed with ristoranti and salumerie (Italian delis), not to mention bakeries, pizzerias, coffee shops, wine shops and cheesemongers. The North End is a required destination for anyone who likes to eat. The Freedom Trail winds through the North End, with stops at Paul Revere House, Old North Church and Copp's Hill Burying Ground. Come during the day to see the sights and learn the history, but be sure to come back at night for dinner.
Seaport District
Best area for harbor views
Separated from Boston proper by the Fort Point Channel, the Seaport District offers all kinds of opportunities to see and savor views of Boston Harbor and Downtown. Follow the HarborWalk around the Moakley Federal Courthouse to enjoy the landscaped parks and fantastic views from Fan Pier, eventually ending up at the Institute of Contemporary Art. Further east, the wharves were once dominated by fish-processing facilities and a marine industrial center. Now, restaurants, bars and retail outlets are opening in the new buildings. The hot dining and drinking scene means that this area is super lively at night. Rooftop bars and restaurants take advantage of the amazing harbor views, while chefs old and new offer their most innovative cooking.
South Boston
Best neighborhood for city beaches
The neighborhood of South Boston remains well off the beaten path. Former stomping ground of Whitey Bulger and preferred setting for Boston-based mafia movies, "Southie" lives large in local and national lore. Despite its reputation, South Boston has its own charm. The waterside community offers great harbor views, as well as Boston's best city beaches. On a hot summer day, Castle Island is a windy, welcoming waterside playscape for families and outdoorsy types. This area is getting a glimpse of the gentrification that has transformed other parts of the city, but Southie is still unapologetically old-school.
Beacon Hill and Boston Common
Best area for quintessential Boston
Abutted by the Boston Common – the nation’s original public park, the centerpiece of the city, and the starting point for the Freedom Trail – and topped with the gold-domed Massachusetts State House, Beacon Hill is the neighborhood most often featured on Boston postcards. But the appeal of this neighborhood lies behind the landmarks, along the narrow cobblestone streets that crisscross the hill. Lined with brick town houses and lit by gas lanterns, these streets make a delightful backdrop for an afternoon meander – whether browsing boutiques and haggling for antiques, or just sipping a coffee and admiring the quintessentially Bostonian landscape.
Charlestown
Best neighborhood for history
Charlestown was incorporated into Boston in 1873, but this neighborhood remains apart, both in terms of geography and atmosphere. On the north shore of the Charles River, it is connected to the rest of the city by the Old Charlestown Bridge. This is the terminus for the Freedom Trail, so many tourists tramp across these historic cobblestone sidewalks to admire the USS Constitution and climb to the top of the Bunker Hill Monument, which towers above the neighborhood. The sights and streets here are not as crowded as those in downtown Boston.
Back Bay
Best neighborhood for people-watching
Back Bay is not as old as some other Boston neighborhoods, nor is it as historically significant. But thanks to magnificent Victorian brownstones and high-minded civic plazas, it is certainly among the loveliest – and a required destination for all Boston visitors. The city’s most fashionable window-shopping, latte-drinking and people-watching area is on Newbury Street, as well as its most elegant architecture, around Copley Square. Its streets lined with stately brownstones and shaded by magnolia trees, it is among Boston's most prestigious addresses. For fresh air and riverside strolling, head to the Charles River Esplanade.
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This article was originally published in July 2021. It was updated August 2021.
