An Insider’s Guide to Boston
One of America’s oldest cities, Boston has an everlasting appeal built on its rich history, storied universities and brownstone-lined streets that are easily explored on foot. This great tradition is enough to inspire a trip, but Boston isn’t just for the history books—there’s way more to do than just see the Freedom Trail and eat lobster rolls.
Most notably, there’s been a major luxury boom in the last year alone. A host of new and renovated five-star hotels in one of its most affluent neighborhoods, the Back Bay, means more reason than ever to splash out like a Kennedy at some of the city’s most coveted addresses like the Raffles and Four Seasons; plus, new restaurants with James Beard Award nods are making it worth the trip to up-and-coming areas like Somerville outside of downtown Boston.
Newfound energy is also palpable in the Seaport, a burgeoning neighborhood on the harbor that’s home to newly developed high rises, shopping and tech companies: anything and everything of-the-moment in Boston. And no trip would be complete without a day trip to Cambridge, with a stop at the Harvard campus.
Take it from a Boston local: This is an exciting time to explore revitalized neighborhoods while staying steps from high-end shopping, the city’s biggest sights and a host of impressive new fine dining and wine bars, especially as the city gears up for the 250th anniversary of Paul Revere’s ride in 2025. Whether you’re a local who wants to treat yourself to the best the city has to offer or you’re only in town for a few days, this is how to plan a luxurious getaway in Massachusetts’s capital city.
The Best Boston Travel Guide
- Raffles Boston
- The Newbury Boston
- Four Seasons Hotel Boston
- The Whitney Hotel
- Mooncusser
- Krasi
- O Ya
- Field and Vine
- Row 34
- Haley.Henry
- Farmacia
- Oak Long Bar + Kitchen
- Boston Public Garden and Newbury St.
- Isabella Stewart Gardner Museum
- Beacon Hill Books and Café
- Courtyard Tea Room
- Fenway Park Private Tour
- South End Shopping
Where To Stay
Raffles Boston
- 40 Trinity Place, Boston, MA 02116
For easy access to Boston’s best shopping and historical sites, this swanky new hotel in the Back Bay is the perfect place to base yourself. Open since 2023, Raffles brings the five-star elegance of the Singapore brand to the area in a big way, as you’d expect from its first North American property. The spacious rooms and suites, Portuguese-New England fusion restaurant Amar and Guerlain spa can’t be outdone, except maybe by the hotel’s attentive butlers. Head to the 17th-floor Long Bar & Terrace for a spectacular city view, a lobster roll and a sip of the Boston Sling, a local rendition of the drink made famous in Singapore.
The Newbury Boston
- 1 Newbury St, Boston, MA 02116
Just steps from the Boston Public Garden and high-end shops of Newbury Street (the lobby is attached to Tiffany’s), this independent Back Bay luxury hotel checks all the boxes and then some: location, dining and lavish comfort. It retains the glamour from its 1927 beginning as a Ritz-Carlton, but the 2021 head-to-toe renovation brought modern conveniences; rooms were widened to allow for bigger showers and spaces are bright, airy, and contemporary. 80 percent of the 286 rooms have views of Boston Public Garden or the city, and 42 have wood-burning fireplaces with a menu of woods (maple for a fast burn, or cherry for a fragrant slow one), plus fireplaces butlers who tend to them. Rooftop Italian restaurant Contessa is a hot ticket for dinner, with memorable city views.
Four Seasons Hotel Boston
- 200 Boylston St, Boston, MA 02116
It doesn’t get more posh than the Four Seasons Boston, which is dripping in luxury, from its cushy rooms overlooking the Boston Public Garden to its wellness space with indulgent spa treatments. Fresh off a renovation in 2023, public areas are newly revived in a nod to the Public Garden across the street with a pleasant Victorian, foliage-inspired revamp that’s nothing short of sanctuary-like. There’s also a buzzy new cocktail bar and restaurant, Coterie. You’ll spare no expense to stay here, but it’s unforgettable and the central location unbeatable. While this property is more New England traditional, if you prefer a more modern vibe, try the Four Seasons Hotel One Dalton Street.
The Whitney Hotel
- 170 Charles St, Boston, MA 02114
The Back Bay may have the highest concentration of new luxury offerings, but this worthy pick in historic Beacon Hill gives them a run for their money. If you’re a traveler who appreciates boutique charm—something that a five-star international chain just can’t give you—this intimate 65-room hotel is the hidden gem you’re looking for, and it was just awarded two Michelin keys to prove it. You’re steps from must-visit sites like the Charles River Esplanade and Boston Common and Public Garden, and it feels more like the exclusive privilege of staying in a friend’s historic brownstone than in a cookie cutter hotel. The downstairs restaurant and bar Peregrine is worthy of special occasions, and it’s got thoughtful touches like help setting up yacht rentals on the Charles River and pet-friendly rooms.
Where To Eat
Mooncusser
- 304 Stuart St, Boston, MA 02116
Boston just wouldn’t be Boston without its fresh New England seafood, and this elegant fish house in the Back Bay overlooking Saunders Castle serves it up with finesse alongside accommodating white linen tablecloth service that’s anything but stuffy. Known for their four-course dinners and a changing menu that evolves every six weeks, this is a meal that doesn’t shy away from global spices and memorable cooking with wine pairings to match.
Krasi
- 48 Gloucester Street Boston, MA 02115
Mouthwatering meze is just the beginning of the appeal at this upscale Greek wine bar in the Back Bay that consistently wins local accolades. It also has the second largest all-Greek wine list in the country, showcasing Greece’s popular grapes as well as rare indigenous profiles. Lesser-known Mediterranean dishes like xtapodi (octopus souvlaki) and giouvetsi (braised lamb shank) shine, and it’s especially fun to order the tzatziki made tableside. This is just the kind of chic neighborhood spot you hear about from locals in the know and love coming back to—when you can snag a reservation, that is.
O Ya
- 9 East Street, Boston, MA 02111
For special occasions and major treat-yourself moments, Bostonians head to this high-end omakase hotspot in the Leather District, which is nothing short of divine. With a chef’s menu of 20 courses of nigiri, sashimi, and other cooked dishes paired with wine and sake if you choose, it’s an epic journey through delicate Japanese flavors that will stick with you long after you leave. It’s no wonder A-listers like Blake Lively and Ryan Reynolds have been spotted here.
Field and Vine
- 9 Sanborn Court, Somerville MA 02143
Overflowing with greenery and hidden away behind an unmarked door in an alley, this trendy spot for fresh, farm-to-table small plates is worth the hop over to Somerville’s Union Square, one of the Boston area’s most up-and-coming food neighborhoods. The vegetable-forward menu highlights local seasonal produce in inventive ways, such as heirloom tomatoes, delicata squash and grilled fish with curried pumpkin purée, in addition to that old Boston favorite: fresh oysters.
Row 34
- 383 Congress St, Boston, MA 02210
For an elevated take on lobster rolls, New England clam chowder and a selection of fresh East Coast oysters, locals head to this upscale-casual restaurant in a former warehouse in the Seaport. They source their fresh fish straight from the Fish Pier, so it’s always a solid bet for the freshest catch. There’s an excellent craft beer list and sports games on TV at the frenetic bar, but you can also have an intimate meal with friends under the low lights here.
Where To Drink
Haley.Henry
- 45 Province St, Boston, MA 02108
Tucked into downtown, this cozy gem boasts one of the city’s best wine curations; in fact, it was a 2024 James Beard Semi-Finalist for Outstanding Wine Program. Sit back, relax and let the thoughtful staff suggest a glass or bottle. They’ll pair your natural, orange and funky bio wines and sumptuous world-class reds and whites with a creative array of fresh seasonal plates, charcuterie and tinned fish.
Farmacia
- 5 N Square, Boston, MA 02128
If you can snag reservations to this exclusive two-hour ticketed experience (released a month in advance), you’ll sip some of the best cocktails Boston has to offer. The unmarked, 9-seat bar just next to Paul Revere’s House in the North End offers an intimate, curated experience with cocktails crafted from a rotating themed menu such as “Autumn Flavors of New England” highlighting local ingredients like cranberries, or “Tropic Thunder” exploring citrusy tropical flavors that eradicate the winter doldrums. It’s unforgettable, and a far cry from the packed touristy bars in this part of town off the Freedom Trail. The best part? You’ll get to talking with owner and bartender Phillip Rolfe over the course of a few hours and learn a lot about the local happenings.
Oak Long Bar + Kitchen
- 138 St. James Ave, Boston, MA 02116
The Fairmont Copley Plaza Hotel, across the street from Copley Square, is a Boston landmark dating back to 1912, but the classic bar inside is also a sophisticated spot to sip wine and cocktails in the Back Bay neighborhood. There’s plenty of leather seating under the grand, chandelier-covered ceiling, so it’s especially good for big parties; they also serve breakfast, lunch, dinner, and brunch, too (and yes, there’s a lobster roll on the menu). This is a good one to know about if you’re ending the night in Back Bay and need to slip in somewhere with a consistently good scene, sans reservations. See if you can spot the remnants of a merry-go-round track on the floor of the bar, where there was once a working merry-go-round in the days post Prohibition.
What To Do
Boston Public Garden and Newbury St.
- 4 Charles St, Boston, MA 02116
Flaunting the yellow foliage of elms in fall and vibrant flower beds in spring, this garden, established in 1837—the the first public botanical garden in the U.S —is the heart of Boston. Swan Boats still give tours on the pond as they have for more than 100 years, while couples linger on the bridge for photo ops and kids take pictures with the Make Way for Ducklings statues at the main entrance. It’s not just for visitors though; this is where Beacon Hill families go to picnic with their Tatte lattes and breakfast sandwiches before shopping on Newbury Street, essentially the Fifth Avenue of Boston, with high-end stores like Tiffany’s and Chanel.
Isabella Stewart Gardner Museum
- 25 Evans Way, Boston, MA 02115
If you only have time for one art museum in Boston (and there are many worthy of a visit: the Museum of Fine Arts and Institute of Contemporary Art in the Seaport District included), make it this one. While the Venetian palace-style museum is filled with American, European and Asian masterpieces, you won’t know which is more breathtaking: the Manet, Vermeer and Rembrandt, or the breathtaking courtyard filled with flowers. Peep the eerily empty frames of several paintings stolen in 1990 that still promise a $10 million reward.
Beacon Hill Books and Café
- 71 Charles St., Boston, MA 02114
An atmospheric 1800s brownstone that was once home to a globe-maker was renovated into the most charming local bookshop on Charles Street, the historic Beacon Hill’s boutique shopping street just across from the Boston Common. At five stories tall, it not only has tons of charming nooks and crannies to hole up with the latest reads, but also a café on the ground floor that locals love. With indoor and outdoor seating, it’s the spot for a delicious breakfast or lunch on the street while perusing the latest, and is especially atmospheric in December when it’s bedecked in holiday cheer.
Courtyard Tea Room
- 700 Boylston St, Boston, MA 02116
Who says Bostonians don’t love a little tea party? While the grand halls of the Boston Public Library are worth a visit just to see the courtyard, marble staircase flanked with regal lions and gorgeous Bates Hall study room, locals know the real draw is a visit to the Courtyard Tea Room. Book Tuesday through Sunday ($72 per person) and pop downstairs for elegant tiered trays of scones, pastries, finger sandwiches and one of more than 20 brew —or bubbles—that will revive you for a night out.
Fenway Park Private Tour
- 4 Jersey St, Boston, MA 02215
Before or after a Boston Red Sox game is a great time to book a tour of one of the oldest and most beloved ballparks in the country. Instead of going with the general public, you can make the tour a bit more special by arranging for a private tour package through the official Tours of Fenway, savoring views from on top of the famous 37-foot left field wall, the Green Monster. Afterward, head to the casual sports bar Bleacher Bar to grab a pint overlooking the field, and you’ll experience firsthand Boston’s legendary love of sports.
South End Shopping
- Dartmouth St., Tremont St. and Shawmut Ave.
Sure, most travelers know about the mainstream, big brand shopping on Newbury Street and in the Prudential Center, not to mention beloved top-end brands (think: Le Labo, Lululemon, Mejuri and Away) at the Seaport, but locals will tell you the place to go for truly one-of-a-kind pieces is actually the city’s South End. This residential area of historic brownstones is dappled with cozy wine bars and irresistible independent boutiques, where you’ll find a host of small businesses like gift shops, women’s clothing boutiques, interior design stores and épiceries. Top spots include women-owned Gifted for handmade Boston keepsakes like tea towels and coasters, mother-daughter-run Flock for well-curated boho-chic women’s clothing, Lekker Home for serious interior design inspo and Formaggio Kitchen for cheese, wine and charcuterie to cap off a brilliant trip.