In a city where history whispers through cobblestone streets and innovation thrives in world-class institutions, Boston is an exceptional tapestry of old and new. Because of its manageable size, you might forget that Boston is, in fact, America’s oldest big city. Time has enriched this New England gem with an exceptional culinary scene and abundant cultural experiences. The new MGM Music Hall at Fenway is a 5,000-seat concert venue that hosts world-class performances from artists like the Yeah Yeah Yeahs, Boyz II Men, and Mitski, all on the calendar this season. Boston is also arguably America’s largest college town, with over 50 higher-education institutions and countless storied pubs where students and teachers have swapped world-changing ideas for centuries. And with the opening of several new hotels, including the first Raffles property in North America, there’s never been a better time to uncover the treasures of Boston, past and present.
Where To Stay in Boston
Raffles Boston
Raffles is the latest luxury property to open in Boston, and true to the brand, the hotel celebrates its literary heritage and global viewpoint through its impeccable design. It was inspired, in part, by the city’s Emerald Necklace—a string of interconnected parks designed by landscape architect Frederick Olmsted in the late 19th century. From the unassuming entrance on Stuart Street, guests are guided to the 17th-floor lobby, also called the “The Writer’s Room,” a Raffles flagship experience inspired by the writers who spent time at the hotel’s infamous Long Bar in Singapore. There is a Long Bar in Boston, too, as well as Amar, its signature restaurant featuring Portuguese cuisine under executive chef George Mendes. The botanical influences resonate throughout, but Blind Duck, the forthcoming speakeasy, takes it to an entirely different level—floor-to-ceiling floral wallcoverings and a deep green palette will make you feel like you’re enjoying bartender Roger Avila’s signature Singapore Sling in the middle of a hidden forest.
The grand spiral staircase in the main lobby provides sweeping views of the city, and public and private spaces reference Boston’s Back Bay. It is designed to make guests feel like they’re staying in one of the neighborhood’s iconic brownstones. In the guest rooms, revolutionary flourishes like copper accents inspired by Paul Revere’s copper plating company blend with mid-century modern furnishings as a play on Boston’s iconic history and architecture. Bath amenities are by Guerlain, the brand behind the forthcoming spa, and the private bars in every room feature local spirits.
A Raffles experience is only complete with its celebrated butler service. Whether arranging a private dining experience, drawing a bath to the perfect temperature, or offering expert advice on local attractions, Raffles butlers go above and beyond to ensure a seamless and memorable stay for every guest. In Boston, they can get you a meet and greet with your favorite Red Sox player or a private Museum of Fine Arts tour. All you have to do is ask.
What To Do: Walk
The Emerald Necklace
The best way to see Boston is to walk, and Frederick Olmstead had that in mind when he created the park system. In 1870, he said, “We want a ground to which people may easily go when the day’s work is done, and where they may stroll for an hour, seeing, hearing, and feeling nothing of the bustle and jar of the streets where they shall, in effect, find the city put far away from them…”
Take advantage of his guidance with a walking tour of the Emerald Necklace, a green oasis amidst the city. Begin your journey at the Boston Common, the southernmost point of the Emerald Necklace and America’s oldest public park. From there, you can hit the Public Garden and Commonwealth Avenue Mall, a tree-lined promenade with beautiful Victorian brownstones, statues, and a central greenway. Other notable locations include Kelleher Rose Garden, a delightful spot with over 1,500 rose bushes, and the Overlook, which provides a fantastic view of the city skyline. Learn more about the Emerald Necklace and grab a map here.
Isabella Stewart Gardner Museum
Isabella Stewart Gardner was a prominent American art collector and philanthropist known for her eclectic tastes and deep appreciation for the arts. She traveled extensively and accumulated a remarkable collection of European, Asian, and American art. Her museum, a Venetian palace-inspired building, is a testament to her passion for art and culture. Its collection features works from Vermeer, Rembrandt, and John Singer Sargent. The museum is also famous for an ongoing mystery—in March 1990, 13 works of art were stolen from the museum. (The thieves remain at large.) Among the pieces stolen were works by Degas and Rembrandt. The museum is offering a $10M reward. Learn more about the theft and the rest of the museum here.
Forget Newbury Street, Hit Charles Street
This iconic street, lined with cobblestone sidewalks, gaslit lanterns, and 19th-century brownstones, is the Boston of your dreams. Located in the Beacon Hill neighborhood, Charles Street encapsulates the essence of old-world Boston and keeps it very local. Grab lunch at Figs pizza, then hit woman-owned December Thieves for gorgeous, modern jewelry, accessories, and home goods from small-batch producers and artisans. Finish off your trip to the neighborhood with a browse and a cup of coffee at Beacon Hill Books and Cafe.
Where to Eat and Drink in Boston
High Street Food Hall
High Street Food Hall is a modern take on the food courts of our youth, organized around the best food and drink that Boston has to offer. It’s a perfect spot to grab fried chicken at Haley Janes and watch a game on the vast LED entertainment system that plays multiple sports games simultaneously. Meet friends for drinks at Daiquiris and Daisies, a craft cocktail counter that makes some of the best drinks in the city. Or for something sparkling, grab a seat at Bubble Bath, a champagne and wine bar that pairs its pours with hot dogs and popcorn.
Little Whale Oyster Bar
Is there anything better than fresh seafood and a crisp glass of champagne? We think not. Any visitor to Boston will eventually cross Newbury Street, named one of the “coolest streets in the world.” When you get there, grab dinner at Little Whale Oyster Bar. The vibe is elegant but casual, the decor a nod to seaside clam shacks (albeit fancy ones). And the menu features the New England-style classics you want when you’re in Boston—lobster rolls (a favorite with diners), fried clams, and a beer-battered fish sandwich served with fries. The drink menu has thoughtfully chosen, seafood-friendly wine and beer offerings.
Krasi
Go to Krasi for any meal—brunch, lunch, dinner, or late night—and you will never get tired of the place or the menu. Krasi means “wine” in Greek, and the expertly sourced all-Greek wine (and spirits) list is something you won’t find in many places outside of the Aegean Islands. The interior is industrial-chic-meets-the-beach, the vibe is convivial and social, and the food menu expands as you need. Nosh on shared plates of charcuterie, freshly baked pita, and dips, or settle into meatier offerings like grilled sea bream and braised short rib.
Hecate Bar
Underneath Krasi is a mystical cocktail bar called Hecate, named for the goddess of magic, witchcraft, and ghosts. Co-owned by Demetri Tsolakis of Krasi upstairs, the subterranean refuge is accessed through an alley door and only holds 24 seats. The experience is inspired by Greek mythology, as is the cocktail menu. Presented in a leather-bound book, each cocktail has a backstory and is a complex mixture of spirits you’ve probably never heard of before. You could call it a speakeasy, but a password is not required—all you need is the knowledge that it exists, and a reservation.
Wally’s Cafe
Wally’s Cafe, the iconic jazz club in the heart of Boston’s South End, is one of the oldest continuously operating jazz clubs in the United States. Founded in 1947 by Joseph L. Walcott, the first Black owner of a nightclub in Boston, Wally’s maintains a no-frills, intimate vibe. With three live music sets each night, catching a great show is easy. It’s also where you’ll see some of Boston’s up-and-coming local talent from prestigious music schools like Berkeley.
