Boston is rich in culture, offers more ground-breaking “firsts” than you can count and has a sizzling food and beverage scene, so planning a two-day adventure in “America’s Walking City” takes a little bit of curating.
Whether you want to spend a day exploring world-class museums, diving into colonial history, meandering through charming neighborhoods, sampling the creations of the city’s top chefs or a combination of everything, here are recommendations of some of our favorite Boston spots.
Day One
Forbes Travel Guide Four-Star The Newbury Boston in the city’s fashionable Back Bay neighborhood is a wonderful choice for your stay. The landmark building exudes classic Massachusetts charm, with a reading space reserved for guests curated by the Boston Public Library. You will appreciate design details such as the lobby’s polished black-and-pearl herringbone floors and superb views of Boston’s Public Garden.
Speaking of the Public Garden, America’s first public botanical garden is home to the historic human-pedaled Swan Boats, which you can ride from April through September. Across the street is Boston Common, the country’s oldest park, founded in 1634. Inside, you’ll find the Frog Pond, where you can ice skate in winter while overlooking the Massachusetts State House.
Be sure to also pop into the Boston Public Library (one of the first free public libraries in the U.S.) to see famous murals by John Singer Sargent, other gorgeous artwork and Bates Hall, the library’s beautiful reading room. Nearby, you can stop for lunch at the OAK Long Bar + Kitchen at Forbes Travel Guide Recommended Fairmont Copley Plaza.
Afterward, browse the upscale shops on Newbury Street, then head over to Beacon Hill, and follow the Freedom Trail to visit some of Boston’s important historic sites, including Old North Church, the Paul Revere House and the Granary Burying Ground.
Make your way over to the Rose Kennedy Greenway, with more green space to enjoy, plus public art, fountains and a whimsical Boston-themed carousel. You can detour to the North End, Boston’s Italian neighborhood, packed with bars, restaurants and shops, or take in the trendy Seaport District, which also has a slew of dining options. Attractions in this area include the New England Aquarium, the Boston Children’s Museum, the Institute of Contemporary Art and The Boston Tea Party Ships & Museum, offering something for everyone.
After a full day of exploring, return to the Back Bay to get ready for the evening. Dinner at Four-Star Deuxave will be a treat after a busy day. The French restaurant, whose kitchen is led by chef Ryan Zichella, crafts an elegant and refined menu featuring dishes such as seared foie gras and spiced duck breast. For a real treat, let the chef take charge with his seasonal five-course tasting menu. Add the beverage pairing, and all your decisions for the day will be deliciously complete.
If you have energy for an after-dinner aperitif, go about a mile over to Raffles Boston’s two-story speakeasy bar, Blind Duck. The pours and views there are breathtaking.
Day Two
Spend some time in the Fenway-Kenmore neighborhood. Dedicate the morning to the Museum of Fine Arts, Boston, where you can peruse everything from ancient Greek artifacts to modern masterpieces. Opt for a guided tour to get the most out of your visit. A few hours at the museum will barely scratch the surface of the vast collections it holds.
Break for lunch at the museum or walk over to the nearby Isabella Stewart Gardner Museum for a bite at its charming Café G (note: you must check in at the admissions desk before going to the café). After refueling, wander through the stunning Venetian palazzo, which eccentric philanthropist Stewart Gardner built in the early 1900s to showcase her art collection. Highlights include Titian’s Rape of Europa, Giotto’s Presentation of Christ Child in the Temple and John Singer Sargent’s El Jaleo. Also venture over to the Dutch Room and learn how important artwork was stolen in a 1990 heist.
Your next play depends on the day. If the weather and schedule permit, go to America’s oldest Major League Baseball stadium, Fenway Park, for a tour of the beloved venue and try to score tickets for that night’s game. On a behind-the-scenes tour, you’ll see the Green Monster, towering more than 37 feet in left field, hear about iconic moments in franchise history and even get down to the hallowed field.
If the forecast isn’t looking so clear, try your hand at another sport — pickleball. Make the 35-minute drive out to Natick to visit Bosse, a state-of-the-art indoor facility with 21 pickleball courts, a golf simulator and darts lounge. Still, the place’s biggest draw may be its food. Chris Coombs (the chef who once led the culinary team at the aforementioned Deuxave) brings his culinary prowess to Bosse Enoteca, an eatery spotlighting handmade pastas, wood-fired pizzas and other Italian fare, all with courtside views of the pickleball action.
Either route you go, plan on ending your quick stay back at The Newbury Boston’s historic and cozy Street Bar. Here, you can grab a Newbury 75 (Empress Gin, prosecco and lime) while reflecting on all that you’ve seen and putting together a list of all the places you want to check out on your next Boston trip.
