Replete with historic sights, cultural attractions and academic institutions, Boston is a dynamic city with many sides. This is due in part to its patchwork of neighborhoods, each with its own distinct ambiance and attractions.
The historic heart of Boston sits on a small peninsula, tucked in between the Charles River and the Boston Harbor. Not much more than 2 square miles, this area includes Downtown, a dynamic mix of modern commercialism and historic sights; the North End, the city’s Italian enclave; and Beacon Hill, with its quintessential Boston charm.
In the 19th century, as the city grew, the swampland to the south and west were filled in to create new, grand, planned neighborhoods – the South End, Back Bay and Fenway – with wide avenues, graceful architecture and renowned cultural institutions. The city’s most recent transformation took place in the Seaport District, where docks and parking lots morphed into gleaming buildings and endless possibilities. These are Boston’s top neighborhoods to discover.
Downtown
Best for historic sights
This area between the Boston Common and the Boston Harbor is where the city grew up, and it’s still the center of the action. Towering office buildings sit side-by-side with historic edifices from earlier centuries, including Faneuil Hall and Quincy Market. White-collar workers hustle to and fro, while visitors cluster around tour guides in colonial-era garb. The bulk of the Freedom Trail sights are here, as are the Rose Kennedy Greenway and the New England Aquarium. Sure, it’s tourist central, but there’s a lot to do, so you don’t want to miss this essential Boston neighborhood.
Downtown overlaps with the lively theater district, which is where the crowds go after dark. The small district is packed with about a dozen theaters, including the ornate Boston Opera House, as well as a cluster of nightclubs.
Local tip: There are loads of hotels in these side-by-side neighborhoods, but you’ll pay a premium to be in this prime location. Check out the Harborside Inn and HI Boston if you don’t want to break the bank.
North End
Best for Italian eats
For nearly a century, this tight-knit neighborhood was the exclusive domain of Italian immigrants and their descendants, who imported ingredients from the old country and cooked up succulent meats and savory sauces using recipes handed down from their nonnas. The North End’s main drag – Hannover St – is lined with Italian bakeries, cafes, pizzerias and osterias, with plenty of overflow on the surrounding streets. Hit up the very old-school Galleria Umberto for pizza (lunch only) or Modern Pastry for cannoli. You’re spoiled for choice for dinner, but you can’t go wrong at Carmelina’s.
The North End is a fabulous place to stroll and shop and eat. The neighborhood is not as insular as it used to be, but you’ll still catch locals conversing in Italian in the shops and playing bocce in Langoni park. And it’s still the best place to come for a thoroughly satisfying Italian feast.
Beacon Hill
Best for old Boston vibe
Beacon Hill is arguably Boston’s most photogenic neighborhood, thanks to the stately brick Federal row houses that line these streets. Brick sidewalks are lit by gas streetlights and wrought iron fences enclose blooming gardens. The mostly residential neighborhood is a delight to wander and explore. The neighborhood also has a fascinating African American history, highlighted on the Black Heritage Trail.
Beacon Hill’s commercial area is along Charles St, which is lined with antique shops, boutiques, and gift shops – and the resplendent five-story Beacon Hill Books. Charles St is a compact but delightful place to shop, with a few dozen eclectic and independently owned stores. And Tatte Bakery is the perfect place for a coffee break.
Charles St terminates at the Public Garden, which is 24 acres of utter loveliness, landscaped with ponds and flowers and tasteful statuary. It’s a highlight in any season, whether bursting with blooms, awash in colorful foliage or blanketed in snow.
There are a few places to stay on Charles St, including the swanky Liberty Hotel in the refurbished Charles Street jail. Otherwise, it’s a pleasant walk across the Common from many Downtown lodgings.
Seaport District
Best for contemporary culture and nightlife
The Seaport District has grown into a forest of glass and steel structures that loom over one of Boston’s hottest neighborhoods for dining and nightlife. The Boston Convention Center is here, as are the cruise ship terminal and about a dozen hotels, which keep this district crawling with visitors year-round. By day, stroll along the HarborWalk for marvelous city views, stop at the ICA Boston to contemplate the contemporary creations and explore the city streets to discover hidden parks and pop-up shops.
Seafood is the traditional choice for dinner on these former fishing piers, and you’ll still find some of the city’s finest, including Legal Harborside and the raucous Barking Crab. Nowadays, however, there are restaurants serving every cuisine – it’s hard to keep up with the latest and greatest.
The fun in the Seaport District does not stop when the sun goes down. This is also where you’ll find the city’s original craft cocktail bar, Drink, and the much-loved and hyper local Trillium Brewery. There’s also comedy at Laugh Boston, bowling at Kings, dueling pianos at D’s Keys, classic jazz at Capo and country music at Hunter’s Kitchen & Bar. In summer, the neighborhood’s many roof decks are open for cocktails and sea breezes, taking full advantage of the Seaport’s prime location.
South End
Best for art markets and open studios
The South End is home to Boston’s most creative residents and its most vibrant contemporary art scene. The center of the artistry is the SoWa Art & Design District along Huntington Ave, where studios, galleries and boutiques occupy former warehouses. First Fridays are a monthly open studios event, which is lots of fun, and Sunday morning is the SoWa Open Market – a farmers’ market and artist market all in one.
The South End dining scene is diverse and innovative. Try Coppa for Italian cicchetti, Toro for Spanish tapas, Myers & Chang for Asian or B&G Oysters for, well, oysters. The Boston Center for the Arts is a mini cultural hub, home to exhibit space and independent theater groups. For cocktails, head downstairs to the Beehive, an ever-popular bar with live jazz nightly.
There are a handful of hotels in the South End, including some of Boston’s best affordable lodgings at Stay Pineapple and the Revolution Hotel.
Back Bay
Best for Boston architecture
Back Bay is Boston’s most elegant neighborhood, its handsome brownstones lined up along grand avenues. The centerpiece is Copley Square, ringed by three architectural icons: the Beaux-Arts façade of the Boston Public Library, Henry Hobson Richardson’s masterpiece Trinity Church, and the John Hancock Tower, striking in its simplicity. Art and architecture fans could easily pass an afternoon exploring these very different buildings.
Fashionistas and shopaholics will want to hit Newbury St, a one-mile strip of art galleries, local designers and quirky boutiques (and more than a few international chain stores). Don’t miss Newbury Comics for gifts and gimmicks and a wicked good time.
When you’re all shopped out, take a break at one of Back Bay’s many eating establishments. For lunch, you can’t miss with a sandwich from Parish Café or ramen from Santouka. If you’re in the mood for seafood, try the unique offerings at Saltie Girl or the reimagined classics at the Banks Fish House. Many fine hotels are clustered around Copley Sq, but it’s hard to beat the warm welcome at Newbury Guest House.
Fenway
Best for live music and baseball
Baseball fans already know that Fenway is the locale of America’s most beloved ballpark, Fenway Park, home for over a century to the Boston Red Sox. The ballpark is a landmark, for sure, but it’s not the only thing that defines this neighborhood.
Fenway is also home to Boston University, as well as the five smaller Colleges of the Fenway. As such, this is student central, with plenty of cheap eats and raucous nightlife to keep them happy. Check out TimeOut Market for a choice of 14 local restaurants (and one bar) under one roof. For drinking, dancing and live music, the place to go is Lansdowne St. Classy venues like the House of Blues and the new MGM Music Hall compete with smaller and more beloved places like Bill’s Bar and Loretta’s Last Call.
Between students and baseball fans, you might imagine that Fenway is pretty rowdy. But this neighborhood also hosts some of the city’s most esteemed cultural institutions, which are considerably more reserved – namely the Museum of Fine Arts and the Isabella Stewart Gardner Museum, as well as the Boston Symphony Orchestra. So there’s something for everyone in this happening ‘hood.
Accommodations in Fenway are plentiful and diverse, ranging from the affordable Oasis Guesthouse to the swanky Hotel Commonwealth. Our vote goes to the Verb Hotel for its retro, rock-and-roll vibe.
