Destination Boston

Some call it “Beantown”—the locals say “Baaastin”—but either way, Boston, Massachusetts, is one of my favorite places. Surprisingly walkable, its unique neighborhoods are filled with colonial-era history, beautiful parks, diverse culture, culinary excellence, world-class museums, and shopping. Here are some wonderful places to stay, eat, and explore when you visit its cobblestone streets.
The stylish Millennium Bostonian Hotel is just across from historic Faneuil Hall and Quincy Market, one of the nation’s most colorful food courts, with street performers, restaurants, and bars. Whatever your culinary taste, you’ll find it at Quincy Market, and the Millennium Bostonian is a perfect jumping-off point.
The Haymarket Square open-air vegetable and flower market happens every weekend right outside the hotel and is a fabulous place to people-watch. Walk around the corner to Ye Olde Union Oyster House for dinner. Established in 1826, you’ll find authentic New England fare, from whole steamed lobster to raw oysters on the half shell and fresh Boston “Scrod” (the catch of the day.)
The city’s oldest neighborhood, settled around 1630, is just a short stroll from the Millennium. In the early 1900s, the North End became the center of the Italian community, and today, more than 100 family-owned Italian restaurants operate within a few blocks of one another amid delis, bakeries, and coffee shops, which you’ll explore on one of Michele Topor’s North End Market Tours. For four hours, Topor treats her guests to a cooking class on foot, revealing where to buy the best ingredients and how to use them in authentic recipes. As Topor told me, “Your world—and your dinner—will never be the same.” She was right!
The best view of Boston’s waterfront can be had in an elegantly appointed guest room at the Boston Harbor Hotel, situated between Rowes Wharf and the Rose Fitzgerald Kennedy Greenway Conservancy. The hotel’s lobby extends outdoors to a brick patio and stage, where waterfront concerts are held all summer. Nothing like dinner under the stars while watching a Motown review, swing, or blues concert—and Friday is classic outdoor movie night.

Anyone who’s run the Boston Marathon knows about Copley Square in affluent Back Bay, where the great race finishes. This is one of the city’s most architecturally significant areas. H. H. Richardson’s magnificent Trinity Church, completed in 1877, is called one of the finest buildings in the country by the American Institute of Architects and can be toured with a docent. On the opposite end of the spectrum is I. M. Pei’s sixty-story modernist glass John Hancock Tower, with its all-glass elongated parallelogram footprint. Take the art and architectural tour of the Boston Public Library to fully appreciate its impressive interiors, with amazing art, sculpture, and rare John Singer Sargent murals.
When you’re ready for bed, check into the Fairmont Copley Plaza Hotel across the street. This seven-story granite building—sister to The Plaza in New York City—is a striking example of beaux arts architecture, with magnificent fully restored interiors. The stately Oak Bar has been voted as the best place in the city to enjoy a martini and live jazz. And be sure to stop by and meet Catie Copley, the grand old hotel’s black Labrador, whose bed is in the lobby—she’s available to accompany guests on walks.
It would take weeks to tour all the fine museums in Boston, but do not miss the Isabella Stewart Gardner Museum in the Fenway district. Mrs. Gardner died in 1924, and her eclectic private collection of art spans four floors of her fifteenth-century Venetian palace-style home, with a breathtaking garden courtyard atrium. Entire rooms are dedicated to tapestries, European furnishings, and paintings by masters including Rembrandt, Matisse, Botticelli, and Raphael.
Nearby, Brasserie JO is a great place to go for an authentic French supper after a day at the museum—a glass of rosé, a scrumptious frisée salad, and roast chicken is a fine way to unwind in this charming bistro located in the lobby of the hip Colonnade Hotel—the only Boston hotel, by the way, that has a rooftop pool. For a sweeping 360 degree view of the city and harbor, just walk across the street and take the elevator to the Top of the Hub, in the Prudential Tower, for a nightcap in its bar.
Boston’s Public Garden is one of the finest examples of horticultural excellence anywhere. A fun thing to do on a nice afternoon is to take a spin around the garden’s lagoon in one of the giant Elizabethan-era Swan Boats. Just steps away from the garden, you’ll enjoy fine service and luxurious accommodations at Four Seasons Hotel Boston. If you want a truly luxurious dining experience in a timelessly chic setting, set aside a night at the hotel’s famed Aujourd’hui. The seven-course tasting menu with spectacular wine pairings is a culinary marvel.
Right around the corner is Newbury Street, lined with chic boutiques and galleries. Especially visit Louis Boston, an ultra-prestigious cutting-edge collection of fine merchandise. For traditional New England handmade wooden furniture, head to Thos. Moser Cabinetmakers. Every piece is heirloom quality and signed by its maker.
You can’t leave Boston without a trip across the river to Cambridge, home of Harvard University. It’s thrilling to walk through the wrought iron gates of the United States’ oldest learning institution into “Haavad Yaad,” where freshmen have been living in stately brick dorms since 1636. Definitely book a walking tour of Harvard Square with Lively Lore. Spend a morning at the University’s Museum of Natural History, home to the amazing Glass Flowers: 3,000 models of more than 840 plants were hand-blown by a German father-and-son team over 49 years, beginning in 1887. You may not believe it, but they absolutely look real!
Among the most talented chefs in Boston and Cambridge is Jody Adams, proprietress of Rialto Restaurant + Bar in the charming Charles Hotel on Harvard Square. Author of the cookbook In the Hands of a Chef, Adams makes everything from scratch daily, and dinner at Rialto ranks among my all-time top dining experiences in the country.
Boston had me at hello. I’m already planning my return; there’s so much more to see and do in this fine American city.
Written By Robyn Roehm Cannon