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Between the undeniable college town vibe, the charms of Beacon Hill, Newbury Street, and Boston Common, and the ample opportunity for walking, biking, boating, and feasting on some seriously good seafood, Boston offers—well, a lot. Taking on Beantown in one day might seem overwhelming, but we’ve put together an itinerary that will give you a glimpse of some of the finest neighborhoods.
No matter the time of year, this harborside city is buzzing and brimming with fun things to do. Bundle up in the cold months and hole up in cute pubs—or come during the warm season, catch a Red Sox game, and enjoy evenings sipping cocktails on a rooftop bar. Here, our favorite things to do in Boston, all in a perfect, culture-filled 24-hour itinerary.
9:30 a.m.: Hop off the plane, pick up your bags, and take a cab to Newbury Street (about a 35-minute drive), where you’ll grab a quick coffee and breakfast before wandering around the shops (which you could spend hours, and hours, and hours doing). We’re recommending you start your day at Thinking Cup on Newbury, which exclusively serves Stumptown and Third Wave coffee (the really good stuff). Then, just a block over, grab a sit-down breakfast at Tatte Bakery & Cafe, a chic Boston cafe with a Mediterranean-inspired menu by self-taught Israeli-born chef Tzurit Or.
10:30 a.m.: When you’re caffeinated and well-fed, it’ll be time for a stroll down the street, where the shops are bountiful and the storefronts are tempting. You’ll pass high-end designer labels, local boutiques, plenty of cafes, bakeries, and, (most importantly) ice cream shops. Depending on the time of year, it’s likely that this storied Back Bay street will get really busy, really fast, so we suggest doing the shopping portion of your day early on. And for those who are less inclined to want to store-hop, the magnificent Boston Public Library is right around the corner on Boylston Street. The historic Trinity Church and iconic Prudential Center are both within walking distance, too.
11:30 a.m.: Next up: time to enjoy the arts—and Boston sure does deliver in this department. The Museum of Fine Arts is home to almost 450,000 works of fine art, and one of the largest collections of Monets outside France. Take your time strolling through their permanent galleries and traveling exhibitions, and be sure to check out the website in advance to see if there are any special exhibits or tours that you might want to sign up for.
1 p.m.: After taking in all the art you can, you’ll likely be ready for some good eats. Head to the North End, which is also right around the corner from Haymarket (on the metro) and Faneuil Hall. For lunch, head to Neptune Oyster, known for making one of Boston’s best lobster rolls. Neptune is packed at all hours, but going for lunch is something of a seafood life hack. Another seafood hack: you have to get two lobster rolls at Neptune, one served cold with mayo, the other served hot with drawn butter. Scallop crudo and a dozen oysters to start couldn’t hurt either. Following your leisurely lunch (or oyster feast), walk over to Boston Public Market (right across from the North End, between Haymarket and Quincy Market) to dip inside this pretty little farmer’s market, where you’ll find local vendors, delicious snacks at a variety of stalls (think: local honey, smoked fish, fresh cheese, and a whole lot more).
2:30 p.m.: After your fill of fitting rooms, fine art, and oysters, head to the Boston Common Visitor Information Center to begin your Freedom Trail tour. It’ll take you less than 20 minutes to walk up from the North End to Government Center and then along to the Boston Common and Tremont Street. There are a variety of Freedom Trail walking tours that allow visitors to get a glimpse at Boston’s important history, see up to 16 nationally significant sites, and just enjoy the beauty of this stately city. Good news: with options like Revolutionary Woman, Walking Into History, Pirates and Patriots, and of course the Historic Pub Crawl, there’s likely something for everyone. Every tour hovers around 90 minutes long—make sure to wear good walking shoes.
4:30 p.m.: Wrap up your day before dinner with a brew or two. Head to the Seaport, for a local beer (or two) enjoyed by the harbor. Venture to Trillium Brewing Company or Harpoon, both in the heart of the buzzing Seaport district. If beer isn’t your beverage of choice, grab a chilled glass of wine or a cocktail overlooking the water at 75 on Liberty Wharf.
6:30 p.m.: You can’t leave Boston without having a hearty Italian meal. So, for dinner, you’ll head back to the North End (an easy walk from the Seaport) for an exquisite meal on Hanover Street. If you’re into the New England seafood life, try Mare, which is a celebration of Italian and Mediterranean-style seafood dishes. Alternately, for classic Sicilian fare, you might instead try Carmelina’s. No trip to the North End is complete without a cannoli run. The two best cannoli shops in town are also on Hanover Street: Mike’s Pastry and Modern Pastry—both Boston legacies. Get a cannoli from both pastry shops, do a blind taste test, and determine which you like better. As the Bostonians would point out: If you’re a Mike’s fan, you’re a tourist. If you’re a Modern fan, you’re a local.
8 p.m.: While you’re in the North End, and if you’re up for a post-dinner nightcap, grab a drink at Parla, another Italian restaurant in the neighborhood. Between the low-lit Mediterranean vibe and the subtle nods to speakeasy decor, Parla boasts over 25 varieties of bitters, and the bartenders are all about concocting cool original drinks tailor-made to guests’ palates.
Where to Stay
After drinks and dinner, you’ll head to Beacon Hill for a luxurious stay at The Liberty, a Marriott Luxury Collection Hotel, an American Express Fine Hotels and Resorts partner. Once upon a time, this stunning structure was the Charles Street Jail, built in 1851—but don’t let the slightly eerie history freak you out. The hotel architects took the building plan and ran with it, yielding a marvelous hotel with sophisticated accommodations and some of the city’s coolest historic-turned-modern spaces. Be sure to leave time in the morning for a leisurely walk along the Charles River Esplanade before leaving town.
You can also stay at an old favorite turned new hotel by booking a room at The Newbury Boston. The property at 1 Newbury Street was once The Taj Hotel, and in April 2021 will reopen as The Newbury. The Back Bay hotel, next to Boston Public Garden, is a collaboration from hospitality company Highgate and Major Food Group (known for Carbone and a number of acclaimed U.S. restaurants). The 286-room hotel’s renovation was led by Champalimaud Design and features culinary offerings from Major Food Group, including a rooftop restaurant and The Street Bar.