48 Hours in Boston: The Perfect Itinerary

Boston Skyline

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If you’re looking for a New England destination to visit for a weekend, go ahead and book a trip to Boston. It’s easy to get to the city's top attractions in just 48 hours, especially if you take advantage of the MBTA, Boston's public transportation system.

While your itinerary is likely to change based on the time of year you visit (we suggest planning a trip for May, June, September, or October), we've created a sample itinerary to maximize your weekend. From exploring the sites along the Freedom Trail to visiting popular museums and neighborhoods, here's how to spend two days in Boston.

01 of 06

Day 1: Morning

Tarts at Tatte in Boston, Massachusetts, USA
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10 a.m.: Upon landing at Logan International Airport, hop in a taxi or Uber and head to your hotel for check-in. While it’s easy to get around Boston and experience the different areas in one trip, you should still think about where you want to make your home base. If you want to stick close to the Boston Common and the city's best shopping, a hotel in the Back Bay neighborhood (like the Lenox, Sheraton, or Westin) may suit you best. For exploring the Seaport, Fort Point, Downtown and the North End, check out the InterContinental or Envoy Hotel. More information can be found in our roundup of Boston's best boutique hotels.

11 a.m.: Once you’re settled, plan on grabbing a quick bite to eat. You can find Tatte Bakery in nearly every neighborhood for coffee, pastries, egg dishes, avocado toast, and sandwiches. There is Café Nero and Dunkin’ Donuts all over Boston for even faster options. It's your call whether you choose to go heavier on food now or during the next part of the day, which will involve quite a bit of walking.

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02 of 06

Day 1: Afternoon

Paul Revere house in Boston Massachusetts USA
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12 p.m.: Now that you’ve cured your hunger, it’s time to set out for the day, and the best place to start is Boston’s iconic Freedom Trail. This 2.5-mile red brick pathway takes you from the Boston Common—the oldest park in the U.S.—to the USS Constitution and Bunker Hill Monument in Charlestown. It's easy to navigate the Freedom Trail on your own via a free self-guided tour, but guided tours are available as well. You can follow it in either direction.

While the Freedom Trail can be done in an hour without any significant stops, plan for it to take at least two hours. That way, you'll have time to explore the landmarks that most interest you, such as the Faneuil Hall Marketplace. Home to lots of stores and restaurants, this historic shopping center is a great place to grab something else to eat or drink. There are also full restaurants and smaller pop-ups inside Quincy Market.

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03 of 06

Day 1: Evening

Sicilian cannoli with chocolate chips
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6 p.m.: Assuming you started the Freedom Trail at the Boston Common, you’ll wind up in Charlestown. Stick around for dinner on the water at Pier 6, or enjoy delicious pizza at Figs by Todd English. You can also walk or take an Uber back over the bridge to the North End for Italian food. You can’t go wrong with any of the restaurants on Hanover or Salem Street, most of which are authentic, family-owned Italian eateries.

8 p.m.: When you’re done with dinner, grab cannolis and other pastries at Mike's Pastry. Modern Pastry has a delicious assortment of treats as well, plus an underground bar for drinks. Nearby Bricco is known for their espresso martinis, and Lucky's is a great spot for live music. For other nightlife, check out our list of the best bars in Boston.

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04 of 06

Day 2: Morning

Isabella Stewart Gardner Museum

Courtesy of Isabella Stewart Gardner Museum

9 a.m.: If you're with a group or want to try out a few different restaurants in a short period of time, head to the Time Out Market in the Fenway/Kenmore neighborhood. Here, you’ll find a sampling of the area’s top restaurants all under one roof, each one serving up their most popular dishes. Try fresh bagels from Jewish deli Mamaleh’s Delicatessen, donuts from Union Square Donuts, and coffee from George Howell Coffee. 

11 a.m.: Spend your second day in the city exploring one or two of Boston's many museums. If you’re traveling with kids, the Boston Children’s Museum is sure to be a hit, or you can teach them a bit about the city’s history by throwing tea overboard at the Boston Tea Party Ships and Museum. Those interested in art will want to visit the Institute of Contemporary Art, Isabella Stewart Gardner Museum, or the Museum of Fine Arts. Meanwhile, the Museum of Science has more than 500 interactive exhibits, along with shows at the Charles Hayden Planetarium.

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05 of 06

Day 2: Afternoon

Boston Exteriors & Landmarks
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1 p.m.: As long as the weather is nice, having lunch or drinks outdoors—preferably with a rooftop view of the city—is always a good idea. A few options include Legal Harborside, the Envoy Hotel’s Lookout Rooftop & Bar, Ristorante Fiore in the North End, or Six West at South Boston's Cambria Hotel. If the temperature is chilly, try any of the city's top restaurants instead.

3 p.m.: After lunch, spend a couple hours at another one of the city’s top museums. If you prefer to spend part of the day outdoors, go to the Back Bay neighborhood and stroll down Boston’s most popular shopping destination, Newbury Street. This picturesque area is filled with beautiful brownstones and a wide variety of shops and restaurants. Nearby Boylston Street also features the Prudential Center and Copley Place shopping malls.

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06 of 06

Day 2: Evening

Boston skyline along Fort Point
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5 p.m.: If you didn’t already do so, get a pre-dinner cocktail at a restaurant with a view of the city. Or, head to one of Boston's best breweries like Trillium in Fort Point or Night Shift at LoveJoy Wharf. Note that Boston doesn’t have happy hour per city rules, so you’ll unfortunately be paying full price for drinks wherever you go.

7 p.m.: For your second evening in Boston, try out a restaurant in the Seaport or Fort Point. These up-and-coming neighborhoods are both being built up with new restaurants, and offer plenty of lovely views of the Harbor.

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