Between the undeniable college town vibe, the charming streets of Beacon Hill, Newbury, and Boston Commons, 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. We have a feeling that you’ll be planning your next trip before you check into your hotel (heads up: you’ll be spoiled for choice when it comes to accommodations).
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.
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) and is known for delicious breakfast noshes like burritos and smoked salmon bagels. There’s even a dairy-free and gluten-free menu here.
10:30 a.m.: When you’ve had your fill of caffeinating, 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, and happens to be a lovely place to read a book, or attend one of many dynamic events, while waiting for the shopping portion of the morning to conclude.
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 in addition to exploring the exhibits, you can attend unique lectures, take studio art classes, and view classic and indie films, too. Take your time strolling through these stunning pieces, 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.
1:00 p.m.: After taking in all the art you can, you’ll likely be ready for some good eats. It may feel a little touristy, but in the spirit of celebrating Boston’s history, head to Union Oyster House, located right along the Freedom Trail (where you’ll go next)—it’s the oldest restaurant in America. Whether you sit for a dozen oysters or a full lunch, you’ll appreciate the historic vibe of this local haunt. Following your leisurely lunch (or oyster feast), head over to Boston Public 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. The company offers a variety of 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.
4:00 p.m.: Wrap up your day before dinner with a brew or two. Head to either Trillium or Harpoon, both located close to the harbor, for a lovely afternoon spent sipping local beer. Depending on the weather and temperature, we recommend taking a little stroll by the water before heading up to the North End for dinner.
6:00 p.m.: Time for some seriously good eats: for dinner, we’re taking you to the famous North End, where you’ll discover some of the finest Italian cuisine on the East Coast. You’ll be overwhelmed with options—both hole-in-the-wall sorts, markets selling beautiful Italian products, and timeless institutions. We recommend Mamma Maria’s, one of those timeless-institution-types, nestled into a beautiful 19th-century row house. Between the elegantly-appointed private dining rooms and the locally-sourced, classic Italian dishes, you’ll want to savor every moment here. Take note of the way the menu follows the seasons: fall and winter dishes tend to skew Northern Italian, while spring and summer dishes highlight cuisine from the south.
8:00 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.
9:00 p.m.: After drinks and dinner, you’ll head back across town to finish your stay at The Liberty, a Luxury Collection Hotel, in Beacon Hill. 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, comfortable accommodations and some of the city’s coolest historic-turned-modern space. Be sure to leave time in the morning for a leisurely walk along the Charles River Esplanade. And if you're feeling a little more luxe, opt for a stay at the Mandarin Oriental.