The Best Neighborhoods in Boston to Spend a Weekend

From chi-chi Back Bay brownstones to rowdy Fenway pubs.

Whether you’ve new to the city or a repeat offender, Boston is worth the trip no matter the distance. A walkable city filled with historical landmarks at nearly every corner, the area is equipped with both vintage and modern dining destinations, shops, museums, and much more. And to experience Beantown in all its glory, you could do far worse than snuggling up to the locals (we’re friendly, promise!), as Boston is packed with some of the most quaint, eccentric, and bustling neighborhoods in the country. Read on for our list of the best places to visit in and around Boston along with insider info on how to make the most out of your visit.

Fenway/Kenmore Square

As any sports fan will tell you, no Boston sojourn is complete without a trip to Fenway or, if it’s baseball season, catching a Red Sox game with a Fenway Frank in hand. The spirited stomping grounds are not only a go-to for the athletically-inclined, however, but also cater to those looking for a memorable and authentically Boston stay.

Hotel Commonwealth Boston
Hotel Commonwealth Boston

Where to stay: Since Fenway Park draws in a fair amount of tourists, you can choose from an array of accommodations like the boutique Verb Hotel, which pays homage to the history of rock and roll, or Hotel Commonwealth, located just two blocks from the ballpark in picturesque Kenmore Square.

Isabella Stewart Gardner Museum
Isabella Stewart Gardner Museum | LnP images/Shutterstock

Things to do: Getting tickets to a Red Sox game goes without saying, but if you’re looking for other options, the Museum of Fine Arts has you covered with their current Monet exhibit while the Isabella Stewart Gardner Museum details the rich history behind the world-renowned Venetian palazzo. There’s also Time Out Market Boston for donuts, gelato, beer, wine, and so much more including events like jazz-themed brunches and drag bingo. In Kenmore Square, you’ll find a boatload of beloved shops like comic book store Comicopia or Nuggets, selling rare vinyls and out-of-print titles since 1978. You’re also a stone’s throw away from Copley Place, a one-stop-shop for ultimate retail therapy. 

Best restaurants: Craving an eclectic lineup offering a variety of cuisines? You’re in luck. Kicking off the food tour, check out Hojoko, a Japanese restaurant pairing small plates and sushi with craft cocktails and premium sake. Sweet Cheeks Q, brought to you by Top Chef alum Tiffani Faison, is a must for BBQ lovers, while Tiger Mama, chef Faison’s take on Southeast Asian fare, serves everything from spicy okra to fried rice (not to mention some of the best tropical tipples around). Impressive seafood selections top the bill at Eventide Fenway and Citizen Public House & Oyster Bar, Wahlburgers is an essential stop, and Tasty Burger is right around the corner if you’re on a serious burger kick.

Bars and nightlife: Pre- and post-game festivities often rollover to Lansdowne Pub, Game On!, Lucky Strike, Loretta’s, and Bleacher Bar, a favorite among locals and visitors alike for the front row view of Fenway’s centerfield. Another venue brought to you by chef Faison, Fool’s Errand, formerly known as the “adult snack bar,” now hosts private dinners along with a pop-up wine shop every weekend. And you can always avoid the rowdiness with a visit to nathálie on Brookline Avenue—the standout boutique and wine bar highlights small batch, natural, and female-helmed selections. 

South End

This neighborhood’s historic brownstones may cost a pretty penny (rental and otherwise), but this is where the whole “location, location, location” cliché comes in. Locals sacrifice space for walking-distance access to some of the city’s greatest restaurants, parks, art galleries, and indie shops.

Where to stay: This largely residential area is lined with rows upon rows of iconic townhouses, offering up prime Airbnb experiences with options like a luxurious stay smack dab in the heart of the neighborhood to a studio with a private roof deck overlooking the skyline. There’s also the 177-room Revolution Hotel on Berkeley Street, a massive revamp of a former YWCA that offers an affordable yet chic stay.

SoWa Boston
SoWa Boston

Things to do: Bust out your walking shoes, because getting to know this neighborhood means wandering down streets like Tremont, Dartmouth, and Columbus Avenue. Start in the SoWa Art & Design District to witness Boston’s contemporary gallery scene (many longtime spaces have fled the high rents of Newbury Street and resettled here). The area’s lovely boutiques are also worth a stop, from Olives & Grace to Niche, Sault New England, and Wyllo. You can even catch some of these vendors at the weekly SoWa Open Market, an artisan and farmers market featuring food trucks and a much-appreciated beer garden.

Black Lamb
Black Lamb

Best restaurants: When dining in the South End, options abound. Some to consider include B & G Oysters for chowder and stuffed lobster, The Butcher Shop for charcuterie and exciting wines, Black Lamb for classic bistro fare, The Gallows for killer burgers and poutine, Toro for flavor-packed tapas, and Bar Mezzana for quality crostini. If you’re in search of a quick breakfast sandwich or pastry, stop by the renowned Flour Bakery & Cafe (South End Buttery is a close second) by famed chef Joanne Chang. Looking for picnic supplies or hotel room vittles? Swing by specialty shop Formaggio Kitchen, which sells aged-to-perfection meats and cheeses. 

Bars and nightlife: Take your pick from cheeky tiki drinks at the subterranean Shore Leave, beers at the divinely divey Delux Cafe, or a wondrous wine at Barcelona. If it’s live performances you seek, hit up The Beehive or, returning in August, pay your dues at the legendary first Black-owned jazz club in New England, Wally’s Cafe Jazz Club.

Jamaica Plain

Jamaica Plain, AKA “JP,” lures in locals and visitors alike with its funky coffee shops, winding side streets, beautiful greenery, and diverse real estate. Although part of Boston proper, JP feels like its own tiny yet endlessly lively city.

Where to stay: JP is not a typical tourist draw, hence the lack of a traditional hotel scene. Commit instead to exploring the neighborhood’s wide array of architecture by booking a Victorian tower, tree top suite, or an entire brownstone via Airbnb.

Things to do: Begin the day with a stroll to Jamaica Pond or get lost in the Arnold Arboretum, one of Boston’s top spots for those looking to trade the urban hustle and bustle for some fresh air. There’s also Ferris Wheels Bike Shop, in case you prefer zipping along the paved pathways. History buffs shouldn’t skip out on a tour of the 18th-century Loring Greenough House, while shopaholics will revel in the finds at 40 South Street, Boomerangs, and SALMAGUNDI

Best restaurants: One of the more appealing aspects of JP is that eating well doesn’t mean breaking the bank—plus, you’ll be able to dine your way around the globe. There’s The Haven for Scottish fare, El Oriental de Cuba for all things Cuban, JP Seafood Cafe for sushi, Noodle Barn for Vietnamese and Thai, and Little Dipper for all-American eats (the meatloaf is truly divine). Local favorite Ten Tables, a tiny gift of an American bistro, is neighborhood date night central, and just try to resist a dip from ice cream fixture JP Licks (nearby FoMU will placate the vegan set). 

Turtle Swamp Brewing
Turtle Swamp Brewing

Bars and nightlife: Check out live music or weekly “queeraoke” at Midway Cafe, or hit up Brendan Behan, an authentic Irish pub known to attract folks straight from the airport. JP is also home to beloved breweries like Turtle Swamp Brewing and, of course, the official Samuel Adams Brewery, where you can enjoy specialty tours, flights in the taproom, and even sample some rare, barrel-aged stuff. If drinking is not your thing, get your cultural fix at Aviary Gallery, an intimate space that hosts thought-provoking shows from local artists.

South Boston/Seaport

A one-time working class area frequently associated with the Irish Mob, South Boston is now a haven for post-grad young professionals. Meanwhile, the harborside portion of the area is unrecognizable from a generation before, with high rises and chain restaurants occupying formerly vacant lots.

Cambria Hotel Boston, Downtown-South Boston (Boston)
Cambria Hotel Boston, Downtown-South Boston (Boston)

Where to stay: Cambria Hotel Boston, opened in 2019, marks a new era for Southie proper. The luxury West Broadway hotel sports sultry decor, a seasonal rooftop bar, and the hopping onsite restaurant, Six West. Heading towards the scenic waterfront, both YOTEL Boston and The Envoy offer modern rooms and panoramic rooftop bars that make for a perfect ending to your summer night.

Things to do: A long stroll down Broadway, Southie’s main thoroughfare, will give you a strong lay of the land. Do a little shopping at Covet consignment shop, then turn down toward the beach for water views and primo people watching. A quick ride over to the Seaport district affords you the chance to stroll the Harborwalk, gawk at the lapping river, and do some shopping at the LL Bean outpost.

Fox & the Knife
Fox & the Knife

Best restaurants: Among Southie’s long list of reservation-worthy spots, Italian-inspired Fox & the Knife rises to the top. Brought to you by multi-award-winning chef Karen Akunowicz, Fox & the Knife is known for endlessly creative cocktails and homemade pasta. It’s also worth checking out Loco Taqueria & Oyster Bar for terrific tacos, coconut margaritas, and oysters (yes, oysters). For funky local hangouts, Local 149 offers bar snacks and a Moscow Mule made with housemade ginger beer, while Moko is a hidden gem of a sushi joint. Those craving fresh seafood should make a beeline for Yankee Lobster, a no-frills takeout spot right on the water. And if it’s a boozy brunch you’re looking for, look no further than Lincoln Tavern for breakfast pizzas, egg BLTs, and early morning tipples. Finally, a trek to Castle Island for a hot dog and soft-serve from Sullivan’s, a seasonal food shack that reopened for the “summer” back in February, is an absolute must.

Bars and nightlife: Our hot take? Southie might arguably be the best destination for an action-packed night out with famous dives like L Street Tavern (which you may recognize from Good Will Hunting) and Croke Park. The area is also brimming with restaurants turned late-night bars including Capo, Stats, The Broadway, Coppersmith, The Playwright, and as mentioned, both Lincoln and Loco. For a good time in Seaport, Cisco Brewers, Trillium, and Harpoon are ideal for day drinking and come nightfall, Lucky’s Lounge’s live music lineup never disappoints. 

Central Square/Inman Square

Cambridge is Boston’s revered younger sister across the river, synonymous with academia thanks to Harvard and MIT, and more recently recognized for its biotech scene. But if Kendall and Harvard Squares are the area's most well-known neighborhoods (with Davis coming in a close third), Central and Inman offer a much fuller sense of what Cambridge living is really all about. 

Where to stay: Central and Inman don’t really cater to outsiders, thus the dearth of high-rise hotels. But you’re free to peruse Airbnb in search of a renovated townhouse or chic apartment stumbling distance from a classic Irish pub.

Things to do: There’s a wide variety of unique venues sprinkled throughout Central and Inman Square, including vintage vinyl shop Cheapo Records and sewing studio-meets-fabric and yarn shop, gather here. For a cup of coffee or a few moments of peace, grab a latte at 1369 Coffee House, a Portland-esque outpost with two cozy locations, one in Central and one in Inman (we’re partial to the Inman space, complete with an aesthetic that transports you back to the ‘90s).

Little Donkey
Little Donkey

Best restaurants: These two squares house some of the most sought-after restaurants not just in Cambridge, but in all of Greater Boston. Craigie on Main is a must, and not just for chef Tony Maws’ cover model of a burger. Little Donkey and Pagu are both divine spots for international small plates and welcoming service. Puritan & Co. will expose you to the bounty of New England agriculture with its seasonal dishes, and couples looking for romance should set aside two evenings for Pammy’s and Bondir, fireplace-laden escapes serving upmarket cuisine teeming with love and care.

BISq
BISq

Bars and nightlife: Central Square is where locals have been catching live music for decades, primarily at the Middle East and Club Passim. On the Inman side, the Lilypad and The Druid are also great after-dark outposts. Settling in for the evening for a few drinks? The two neighborhoods are awash in unassuming watering holes, from Green Street Grill to Trina’s Starlite Lounge, and for something more intimate, indulge in the extensive wine list at BISq.

Union Square

This tiny Somerville district packs a lot of punch into its square footage, with restaurants, bars, fitness studios, and regular street fests like the annual Fluff Festival, dedicated to our region’s gooey signature sandwich. It encapsulates the wider neighborhood’s too-cool-for-school reputation and attracts every manner of young, plugged-in professional.

The Row Hotel at Assembly Row
The Row Hotel at Assembly Row

Where to stay: The Row Hotel, a newer boutique option in nearby outdoor shopping space Assembly Row, provides you with all the amenities you crave. But if it’s more old-world charm you're after, you can always stay in an updated 1850s Methodist church.

Things to do: Start the day with some upward mobility at Brooklyn Boulders, a cavernous indoor climbing space. After grabbing a Vietnamese coffee at Bloc Cafe and a maple bacon donut from Union Square Donuts (get there early because they always run out), head over to Bow Market, a public courtyard containing more than 30 retail shops, restaurants, and bars. End the day picking up indie wares at Tiny Turns Paperie or grab a scoop or two at Gracie’s Ice Cream.

Field & Vine
Field & Vine

Best restaurants: Most of Union Square’s stellar eateries lie within feet of each other, making it easy to wander around and peruse menus before picking a favorite. For seasonal small plates, hit up Field & Vine, while those in the mood for bratwurst should opt for Bronwyn (cheers to beers in steins!). If you’re up for a splurge, wander a little farther afield to Tasting Counter, a ticketed fine-dining experience like none other, or book a table at Celeste, which serves up Peruvian-inspired shareables in an intimate and incredibly becoming setting.

Variety Bar
Variety Bar

Bars and nightlife: Start your engines with a cocktail at pseudo-speakeasy Backbar, consistently voted one of the best cocktail bars in the country. If you’re after a refreshing pilsner, Aeronaut Brewery introduces you to the local craft brewing scene with various events throughout the week. You could easily spend a whole night drinking your way around Bow Market, home to natural wine bar Rebel Rebel, beer hub Remnant Brewing, and cocktail bars Create Gallery & Cocktail Lounge and Variety Bar. The latter is located inside The Comedy Studio, an excellent place to catch up and coming stand-up acts. Wrap up the evening with a little live music at The Jungle, one of the area's top concert venues.

Back Bay/Beacon Hill

Both the Back Bay and Beacon Hill are bastions of old-world living, with even more alluring brownstones, gas lamp posts, and cobblestoned streets to admire. The area also lays claim to one of the most photographed streets in the US—none other than Acorn Street, that is, a private way that transports you back to the country’s humble beginnings.  

Where to stay: In Back Bay, you have two high-end options: the Mandarin Oriental, whose name speaks for itself, and The Colonnade, where the rooms and suites feel more like well-appointed condos. But there’s also a clandestine, budget-friendly option in The College Club of Boston, a bed and breakfast housed inside a brick townhouse on Commonwealth Avenue. If Beacon Hill is your preferred locale, you’ll be hard-pressed to choose between the Whitney Hotel, a welcoming gem of a boutique, and The Liberty Hotel, a large, celebrated modern venture housed inside a former jailhouse. 

Things to do: Stroll the two most iconic streets in all of Boston, of course! Start at the top of Newbury Street for a walk through history, eventually finding yourself among all the finest retail outposts in town, including Chanel, Bulgari, and Dolce & Gabbana. From there, you can cut through the Public Garden, pausing to take in the flower beds and swan boats (weather permitting) before making your way over to Charles Street, which appears trapped in the 19th century. Pop into as many antique shops as you can, but don’t miss the street’s surprisingly chic boutiques, from French & Italian to Ouimillie to December Thieves to Dress Boston. End by cutting over to The Esplanade, a park running alongside the Charles River, to watch the sailboats glide by. And you can even rent a kayak or paddle-board yourself if you prefer to be part of the action.

Buttermilk & Bourbon
Buttermilk & Bourbon

Best restaurants: Get your seafood fix with a lobster roll from Saltie Girl, sky-high raw bar towers at Select Oyster Bar, and lobster-studded pizza at Scampo, located inside The Liberty Hotel. In the other direction, you’ll find New Orleans-inspired Buttermilk & Bourbon, serving up some next-level fried chicken and homemade soft serve. La Voile fulfills your French brasserie dreams and Terra, stashed inside Boston’s Eataly, is heaven for pasta lovers. Beacon Hill’s dining scene is more sedate, but 75 Chestnut is one of those quaint vestiges of the past only found in historic neighborhoods, and Figs is the local go-to for sitdown pizza. The Paramount is a must for breakfast—the wait time is well worth it once those massive pancakes hit your awaiting plate. And make sure to save a little space for an almond croissant from local chain Tatte Bakery.

Alibi Boston
Alibi Boston

Bars and nightlife: If you’re looking for a relaxed, sophisticated night on the town, Beacon Hill and Back Bay are right up your alley. Back Bay’s Lolita is a dimly-lit lair with crafty cocktails and cotton candy on the menu while Citrus & Salt showcases tequila in all forms from prickly pear-pineapple margaritas to guava- and blood orange-spiked tequila-mosas, a spin on the traditional (and sometimes boring) brunch staple. Other hotspots include OAK Long Bar + Kitchen, Back Bay Social Club, and Bukowski’s Tavern. As for Beacon Hill, the Liberty is actually more of a party scene come nightfall, with folks travelling in from all corners dressed to the nines for drinks at wine bar Clink and cocktail spot Alibi. And for a more casual scene, stroll over to the no-frills Sevens Ale House and kick back for a chill night out.

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Jillian Hammell is a contributor for Thrillist.