Boston is called America’s College Town for a reason. The city is home to 35 colleges and universities, and there are more than 100 in the greater Boston area.
Massachusetts’s capital is also rich with history, a flourishing food scene, and hotels—from old sprawling waterfront properties to new, hip boutique inns—which makes it hard to decide how (and where) to spend your time.
If you’re one of the many entering either Boston or Cambridge this spring for commencement festivities, consider this your guide, courtesy of top travel experts.
Where to stay:
Fresh off of a $50 million expansion to double its size in Kenmore Square—and just in time for Big Papi’s final season with the Red Sox—now’s the time to book the iconic Hotel Commonwealth (500 Commonwealth Ave.; 617-933-5000), said Steve Jermanok, co-owner of ActiveTravels.com, a boutique travel agency in Newton. Relax post-ceremony on the new 1,400-square-foot outdoor terrace overlooking Fenway Park, or book an in-room massage. You’re just a stone’s throw from several colleges, with easy access to the Green Line.
This hotel (70 Sleeper St.; 617-338-3030) in Boston’s Seaport District has a rooftop deck that offers some of the best views of the Boston skyline. “You feel as if you’re on the water looking back at the city,” Jermanok said. “If you want to savor that breathtaking view, book the corner suite, room 604, just below the rooftop bar,” he suggested. Floor-to-ceiling windows overlook Boston harbor and the buildings that edge the water. Don’t miss brunch at the hotel’s Outlook Kitchen and Bar in the a.m.
Revere Hotel Boston Common
“Brutalist on the outside, luxurious on the inside,” said Paul Bennett, co-founder of Context Travel, a network of specialists who lead walking seminars in 25 major cities worldwide, of the Revere (200 Stuart St.; 617-482-1800). The boutique hotel sits a few blocks from the Boston Common. See the city from above by lounging at the rooftop pool, enjoy exceptional service, and explore the famed Common.
Where to eat:
“There’s a reason why owner Garrett Harker has been named Restaurateur of the Year by the James Beard Foundation,” said Jermanok of the brasserie-style restaurant in Kenmore Square (528 Commonwealth Ave.; 617-532-9100). “Food is consistently good, the atmosphere is festive, and Harker is known to slip the graduate a flute of champagne or two.”
No trip to Boston is complete with a stop at 11 1/2 Thacher St. in the North End (617-227-0765)—the original Regina’s location that’s swept up number-one pizza in Boston accolades (and celeb endorsements) throughout the years. The ambience is not to be missed, Bennett said. (And if you’re craving dessert afterward, forgo a cannoli at Mike’s Pastry for one at the lesser-known Modern Pastry, said Bennett.)
The Barking Crab
This casual, warm-weather spot (88 Sleeper St., 617-426-2722) is an easy walk from anywhere in the Seaport. Sit family-style at picnic tables and dive into a lobster roll, steamers, grilled fish sandwiches, and crab, Jermanok said. “Lighted lobster traps dangle down from a red and yellow tent that’s used to shade the open-air restaurant.”
What to do:
Row the Charles River care of Charles River Canoe & Kayak
If you really want to get to know that Dirty Water that the Standells sung about, head over to the the Charles itself. Paddling the scenic city river is a must-do, Bennett said. Via Charles River Canoe & Kayak (four locations in the area, including one in Boston; 617-965-5110), you’ll see Boston on one side of the Charles and Cambridge on the other, pass local colleges and picnic spots like the Esplanade, and take in a unique view of the city skyline.
See the city on two wheels via Hubway
Rather stay on solid ground? “Take advantage of Boston’s public Hubway bikes to see the city on wheels,” Bennett said. “Biking along the river…is particularly lovely.” You can find station stops all over the city. (Check out the map here.)
Stroll Arnold Arboretum
If you’re a nature lover, head over to Jamaica Plain, one of Boston’s quirkiest and most historic neighborhoods, to explore Harvard University’s Arnold Arboretum (125 Arborway; 617-524-1718), Bennett said. The collection of flowers, trees, shrubs, and vines, which sits on 281 acres, is one of the most comprehensive on the planet. You’ll forget you’re in the city.
Where to stay:
If you’re fortunate enough to snag a coveted room at the Charles Hotel (One Bennett St., 617-864-1200), do it, Jermanok said. The swanky hotel is home to sweeping views of the Charles, a prime location in the middle of Harvard Square, and a storied history of guests that include celebrities, politicians, and even the Dalai Lama. Get lost staring at the hotel’s walls—many of the paintings here were commissioned for the hotel itself. The pavilion space also includes sketches by John F. Kennedy Jr.
The Kendall Hotel
Families attending MIT graduations will want to book the within-walking-distance Kendall (350 Main St.; 617-577-1300), which “captures the essence of the city, with its patriotic atmosphere and traditional feel,” according to Sarah Gavin, a travel expert at Expedia. The charming hotel, which used to be a firehouse, is a quick walk from tech-infused Kendall Square and a little farther from the eclectic Central Square.
This Kimpton hotel (25 Edwin H. Land Blvd.; 617-868-8000) is like home base for commencement travelers—it’s just minutes from Harvard, MIT, and Beacon Hill. “Kimptons are particularly great for families,” Gavin said. In fact, Hotel Marlowe—a short walk from the Museum of Science—offers complimentary bike and kayak rentals and curated maps of the best ways to see the city on two wheels. Bonus: They’re pet-friendly, so you can bring your dog.
Where to eat:
The Charles Hotel’s upscale brunch spot (One Bennett St.; 617-661-5005) may be pricey, but it is a people-watching paradise. “This is where Boston’s power brokers go to dine on omelets and thick pieces of bacon before starting the day,” Jermanok said. “Last time I was there, I spotted the owner of the Boston Celtics at the table next to me.”
Those sticking around Cambridge should dine at Oleana (134 Hampshire St.; 617-661-0505), Bennett suggested. It’s a picture-perfect graduation dinner scene: a bustling outdoor patio complete with a fountain, herb garden, and an exquisite menu. Expect Mediterranean foods with an Arabic and Turkish. And don’t skip dessert from pastry chef Maura Kilpatrick, who whips up homemade ice creams.
Mr. Bartley’s Gourmet Burgers
The food at this Harvard Square staple (1246 Massachusetts Ave.; 617-354-6559)—which has been going strong since 1960—has been praised by local and national press alike (plus celebrities). So if your weekend calls for a good ol’ burger, make a pit stop, Bennett said. You might have to wait—the line is known to snake out of the building—but wacky decor (the inside looks like a dorm room, decorated with posters and signs) and smells of homemade comfort food will keep you occupied.
What to do:
Visit the Mount Auburn Cemetery
Cambridge is home to the first landscaped cemetery in the U.S., Bennett said. The cemetery (580 Mount Auburn St.; 617-547-7105)—created in 1831—was designed not just as a place for the deceased, but also as a place to enjoy nature, winding paths, and sculptures. Stroll the miles of paths, bird watch, and take in panoramic views from the historic Washington Tower.
Tour Harvard’s campus
Travelers from all over the world head to Cambridge year-round to explore its prestigious universities, said Julie Cassetina, a spokesperson for TripAdvisor. Take advantage of your surroundings by walking through Harvard University’s campus, she said. Find photo opps outside the picturesque pillars of Widener Library; the touristy John Harvard Statue; and the funky, colorful door of The Harvard Lampoon, Harvard’s humor publication that has famous alumni like Conan O’Brien.
Try organic snacks at Life Alive
Need a pick-me-up? Of the no-frills Central Square health-food haven (765 Massachusetts Ave.; 617-354-5433), Cassetina said: “It’s truly an urban oasis that serves the most incredible organic food.” Try the Adventurer: a mix of corn, beets, broccoli, kale, cheddar, tofu or sprouted legumes, and almonds over quinoa and brown rice.