Boston Getaway Guide

Historic meets hip in Beantown.

Boston—aka “The Hub,” “Titletown” and “Athens of America”—more than lives up to its many nicknames. Here, history, culture and wicked-good cuisine collide for a unique urban experience that feels at once distinctly American with a touch of European charm—from its walkable streets and stunning historic neighborhoods to its beautiful parks and waterfront. Both timeless and trendy, the cosmopolitan vibe of the city continues to attract all walks of life, lending to its all-around vibrant feel.  

History buffs can immerse themselves in the city’s revolutionary roots, while foodies can feast their way through the city’s infinite award-winning restos and bars. And sports fans? Between the Red Sox, Pats, Bruins and Celtics, let’s just say Beantown plays to win. With so much to do, see and devour, narrowing down the must-visit spots is nearly impossible. But if you want to experience the absolute best of Boston, here’s where to start. 

DO

Fenway Park 
You don’t have to be a Sox fan to appreciate the magic of MLB’s most beloved—and oldest!—ballpark. Snag a Fenway Frank, sit above the Green Monster (the iconic left field wall), and belt out “Sweet Caroline” in the eighth. After all, it’s not just a game, it’s a lifestyle. mlb.com

SoWa Boston
Packed with galleries, funky boutiques and incredible eats, the Art + Design District in the South End is a creative paradise. Whether you’re an art lover or just a cool vibe connoisseur, there’s something for everyone. Pro tip: Hit up First Fridays to rub elbows with local artists, shop small and try out some of the city’s best food trucks. sowaboston.com

Whale Watching
Fun fact: Thanks to its prime location near the Stellwagen Bank National Marine Sanctuary, Boston is one of the best spots in the world for whale watching. Hop on a three- to four-hour excursion from Long Wharf for a chance to get up-close and personal with the gentle giants of the ocean. cityexperiences.com

Citizens Opera House
For an evening of culture, swing by the beautifully restored 1920s-era theater that plays host to the Boston Ballet, Broadway hits and world-class musicians. The only surviving Boston work of iconic American theater architect Thomas Lamb, the theater itself is a destination offering historical, architectural and backstage tours. Show-stopping, indeed! citizensoperahouse.com

Freedom Trail 
Lace up your sneaks and stroll through time on the 2.5-mile trail connecting some of America’s most iconic landmarks—from the storied sanctuary of King’s Chapel to the Boston Massacre Site, Paul Revere House and the USS Constitution. thefreedomtrail.org

Beacon Hill
Historic row houses, gas lamps, cobblestone streets? Say less. History meets major curb appeal in this residential neighborhood with a dashing dose of old-world charm. Stroll down the famous Acorn Street and pop into Tatte Bakery & Cafe or Beacon Hill Books & Cafe for a cozy caffeine pick-me-up. meetboston.com

EAT

The Banks
When in Boston, eat as the New Englanders do. “Celebrating New England past and present,” Chris Himmel and executive chef/partner Robert Sisca’s fresh seafood spot dishes up all of the classics, from hearty New England clam chowder to melt-in-your-mouth lobster rolls. For a good time, roll up on Sundays for jazz brunch feat. an extensive menu of breakfast faves with a New England twist—think fried clams & waffles and lobster hash. thebanksboston.com

Somaek
It’s all about family at this James Beard 2025 Best New Restaurant semifinalist near Boston Common, which pays homage to chef Jamie Bissonnette’s mother-in-law—also the casual resto’s official consulting chef. Traditional Korean dishes such as seogogi mandu (beef and scallion dumplings), kimchi jjigae (kimchi stew) and jabchae (sweet potato starch noodles) make for an intimate and filling dining experience. somaek.com

Fox & the Knife
Bringing a taste of Modena, Italy, to South Boston, the elevated Italian spot embodies the “spirit of aperitivo” via a curated selection of sharable starters such as housemade ricotta, prosciutto di Parma and harissa-marinated olives. When it comes to mains, dig into the tagliatelle Bolognese, pollo al mattone, pesce fritto or any of the other bold and comforting dishes. foxandtheknife.com

DRINK

Backbar 
Frequently topping the lists of Boston’s best bars, the eclectic spirit-forward speakeasy-style destination is a hidden gem of the city—literally. Down an alley through an understated orange door, street art-covered walls set the stage for carefully crafted cocktails like the Florida Man, The Kraken and the Jackalope. backbarunion.com

Bell in Hand Tavern
Pouring pints since 1795, America’s oldest continuously operating tavern is worth a visit for a round or two and some tasty pub grub. Enjoy Revolutionary era-themed cocktails such as the Paul Revere Punch and Presidential Maple feat. Jefferson VSB Bourbon (naturally) in a cozy historic brick setting. Ring it on! thebellinhand.com

Blossom Bar at Sichuan Garden 
A little bit of Tiki and a lot of Sichuan, this craft cocktail bar and restaurant located in Boston’s Brookline suburb perfectly encapsulates the art of the cocktail with award-winning sips such as the Gloria (Bacardi Cuatro Años, passion fruit, lime, cinnamon, coffee and mascarpone). Together, the beautiful ’tails and delicate light wood-filled and mint-colored interior make for the ultimate ’Gram-worthy experience. blossombarbrookline.com

STAY

The Liberty Hotel
It doesn’t get more “quintessentially Boston” than this lavishly renovated Beacon Hill stay. In 2007, the historic and infamous Charles Street Jail ditched its cells for swanky suites, crafting a luxury experience in the heart of the city. Lean into the theme by dining at Clink., Alibi or one of the hotel’s other jailhouse-chic restaurants and bars. libertyhotel.com

The Verb Hotel
Rock ’n’ roll is the name of the game at this one-of-a-kind midcentury music lovers’ oasis tucked beside Fenway Park. Relax in a retro-luxe hotel room or opt for a one-of-a-kind experience in a music legend-inspired Backstage trailer. In addition to the ballpark, the surrounding neighborhood is home to the House of Blues, MGM Music Hall, and ample bars and restaurants. theverbhotel.com

The Langham 
Sleek and sophisticated, this centrally located hotel formerly housing the Federal Reserve Bank of Boston blends the new with the old through thoughtful nods to the city’s history—think art, architecture and other elements. From warming gold and plaid accents to British-inspired cocktail bar The Fed, you can also expect touches of Europe. langhamhotels.com