Back Bay/Beacon Hill
Want to live (temporarily) among the Brahmins? You have your choice between Boston’s two choicest neighborhoods. Both the Back Bay and Beacon Hill are bastions of old-world living, with tony brownstones, gas lamp posts, and cobblestoned streets. But a quick note to visitors: Though charming side alleys like Acorn Street are frequently photographed for their Founding Fathers feel, be respectful of the residents who live there while adding to your Instagram feed.
Where to stay: In the Back Bay, you have two splurge 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 photogenic Commonwealth Avenue. If Beacon Hill is your preferred locale, you’ll be hard-pressed to choose between the newly opened Whitney Hotel, a welcoming gem of a boutique space, and The Liberty Hotel, a vast and celebrated modern spot housed inside a former jailhouse.
Things to do: Stroll the two most iconic streets in Boston. Start at the top of Newbury Street for a walk through history, eventually finding yourself amongst all the finest boutiques in town, including Chanel, Bulgari, and Dolce & Gabbana. From there, you can cut through the Public Garden, pausing to admire the flower beds and swan boats (weather permitting) before heading over to Charles Street, which still seems charmingly 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, the park that runs alongside the Charles River, and watching sailboats glide by.
Best restaurants: There’s no better time to get your seafood fix and dine at Saltie Girl for a lobster roll, Select Oyster Bar for seafood towers, and Scampo for lobster pizza. Swinging in the other direction, Buttermilk & Bourbon has a New Orleans feel and next-level buttermilk fried chicken (and oh, that homemade soft serve!). La Voile grants you classic French bistro fare and Terra, inside Boston’s Eataly, is a grilled-meat dream. Beacon Hill’s dining scene is more sedate, but 75 Chestnut is one of those quaint spaces that’s only found in a historic neighborhood, and Figs is the local go-to for sitdown pizza. The Paramount is a must for breakfast -- the wait time is worth it for those massive pancakes dished out luncheonette style. Just save a little space for an almond croissant from local chain Tatte Bakery.
Bars and nightlife: Locals don’t think of either neighborhood as party spots -- Beacon Hill, in particular, can feel like a bit of a bedroom community. But you don’t have to dig that deep to find a late-night scene. In the Back Bay, Lolita is a sexy lair where professional singles truly mingle; ditto Oak Long Bar + Kitchen, where you also might spot a local pro athlete or two. Back Bay Social Club is for the younger folks, while Bukowski houses the city’s surly beer drinkers. As for Beacon Hill, the Liberty is actually a genuine party scene, with folks coming from the suburbs dressed to the nines and hitting up wine bar Clink and cocktail spot Alibi. The casually dressed, meanwhile, might do better at the no-frills Sevens Ale House.