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Overview

Are you spending a weekend in Boston? As one of the oldest cities in the nation, it is steeped in culture and American history. There’s an overwhelming amount of sights to see, and tackling the entirety of the city will take days. The city’s historical roots also make it a little difficult to navigate since its streets are not laid out in a simple grid orientation.

Don’t stress about cramming a week’s worth of activities into three days. This 72-hour itinerary highlights the must-see spots of the city for an extended enjoyable weekend.

Boston is the largest city in New England. Located in the upper Northeast of the country, it’s a bit of a trek to get to Boston if you’re coming from the other side of the country. It has easy connections via air, however, and once you’re there, you can get around simply without a car.

Logan International Airport (BOS) is a major focus for both JetBlue and Delta. It’s not uncommon to find good deals to the city for around $100 round trip (or less) in certain seasons. Round trip flights below $200 round trip are definitely doable from most places.

Location

Boston, MA, USA. 

Activities

Eating, History, Art

Duration

2-3 days

Getting There

Boston is in the very northeastern part of the country. Unless you’re in New England or Mid-Atlantic states, that makes Boston a trek by car. If you’re headed out by car for the weekend, Boston is only around 4 hours (depending on traffic) from NYC. Coming from the north, Portland, Maine, is just 2 hours away.

Unlike other parts of the country, the Northeast has frequent train service. If you don’t want to worry about traffic and parking, skip the car and take Amtrak between Boston and NYC. It will take around the same amount of time. Coach tickets can be found for as low as $30.

Boston is a focus city for Delta and a major hub for JetBlue when it comes to air travel. Particularly on JetBlue, great deals can regularly be found for under $200 to most major metro areas. We’ve planned out an itinerary starting Friday afternoon, so plan on arriving in the morning to maximize your weekend getaway. Otherwise, just skip down to dinner activities.

Boston Logan is one of the few airports close to the downtown core. With great public transportation options available in Boston, getting to and from the airport isn’t a chore.

  • Public Transportation: Massachusetts Bay Transportation Authority (MBTA)’s subway, known as “the T,” has a dedicated Airport Station complete with bus shuttles to the terminals. The Silver Line bus is always free to/from the airport. A one-way on the subway Blue Line is $2.40.
  • Rideshare/Taxis: Your traditional rideshare and taxi options are available. It takes only about 10-15 min. to get into downtown for around $25.
  • Car Rental: Boston has the typical array of rental car companies offering their services at the airport. However, the immediate Boston area has extensive public transportation options; having a car is almost more of a headache. You don’t really need one unless you’re headed to the Boston suburbs and exurbs.
a view of the boston skyline next to the water

Where to Stay

As the 11th biggest metro area in the U.S., Boston has a wide array of accommodations from which to choose. The city hosts many conventions and events throughout the year, so finding a room won’t be a problem. But the city’s roots in American history draw many visitors, so the closer you get to downtown, the more expensive things become. If you want to visit during events like St. Patrick’s Day or the Boston Marathon, be prepared to pay upwards of $300 a night.

For a somewhat cheaper choice, try looking at the Aloft Boston Seaport District. We were finding rooms for around $110 per night, but prices fluctuate according to the travel season. If you’re a Marriott Bonvoy member, you can use your points at this quirky hotel. Rooms are colorful and chic. The location in the Seaport District is right across from the convention center and the Lawn On D (an open-air activity site). The Institute of Contemporary Art is also in the area, as is the trendy eatery Chickadee and Harpoon Brewery.

If you’re looking for a more boutique experience, try the Bostonian Boston. Here, you’ll be in the thick of things, as it’s just across the street from Faneuil Hall and Quincy Market. Many rooms have a Juliette balcony for you to look out onto the hustle and bustle below. The Bostonian is within walking distance of the Old State House, City Hall, North End, and the Freedom Trail. Plus, the airport is only a 10-minute drive away. All this for around $200 a night, depending on the season.

the landscape of the boston public garden

Friday Afternoon: Stretch Those Legs

If you want to maximize your time in the city over a 3-day weekend, take an early flight so that you arrive in the early afternoon. If you’re coming from further away, however, you may not arrive until early evening. No worries! The Freedom Trail is waiting for you at your leisure. A literal trail is marked on the sidewalks in brick or red paint and follows a symbolic trail of historical locations in the center of Boston. You can walk a self-guided tour by yourself or you can purchase tickets for a guided version with actors dressed as prominent figures. It’s a good way to orient yourself in the city, and you’ll see the gravesites of founding fathers Samuel Adams and John Hancock, explore Paul Revere’s house, and finish at the location of “Old Ironsides," the USS Constitution.

But if you want something more leisurely, take a stroll through Boston Common and Public Garden to enjoy the greenspace. This is a popular tourist spot dotted with statues dedicated to President George Washington and the children’s book Make Way for Ducklings. You can ride swan boats in the lagoon, too. If you need to wet your whistle, you can cross the street to Cheers and live out your favorite sitcom fantasy.

Freedom Trail emblem

Friday Evening: A Waterfront Dinner

After having some time to head back to your hotel room and freshen up after all that walking (or checking in if you’re arriving later in the evening), it’s time to head to the North End. We suggest Boston Sail Loft as the perfect dinner spot. It’s right on the waterfront, and you can have your dinner surrounded by boats as the sun sets. It has the usual array of fresh seafood (Hello! It’s right on the water!), but the standout is the clam chowder. It’s some of the best chowder in the city and a perfect representative of New England clam chowder overall.

Boston

Saturday Morning: Caffeine Fuel-Up

On Saturday, we headed to the Fenway–Kenmore area. If you need to fuel up for a full day’s worth of activities, then stop by the Boston breakfast institution Tatte Bakery & Café. There are multiple locations around the city, but the closest one to your afternoon activity is in the Northeastern University area. Tatte has the full range of breakfast menu items, from all your favorite egg dishes to heavier brunch sandwiches. Maybe you just need caffeine to start your day and a simple muffin. That’s here, too, with a nice table to sit at under some trees.

Saturday Afternoon: Museum of Fine Arts Boston

You’ll have to devote an entire afternoon to the MFA, but if you’re an art enthusiast, it’ll be a day well spent. This massive museum has a large permanent collection, but it also hosts multiple traveling exhibitions. You could honestly spend multiple days here and still not have seen everything. Tickets are $25 (or free if you happen to be a member), and special exhibitions cost a little extra on top of that base price.

2008-03-22 03-23 Boston 093 Museum of Fine Arts

The MFA has two floors and a basement, two gift shops, a restaurant, cafe, and wine bar. You’ll see everything from ancient Egyptian sarcophagi to contemporary American art; you can even watch old pieces being restored. Beyond its permanent works, the museum hosts an array of remarkable exhibitions. While I was visiting, the MFA hosted an exhibit of Leonardo Da Vinci’s sketches in addition to a gallery dedicated to Katsushika Hokusai, the Japanese artist behind Under the Wave of Kanagawa. His iconic painting is also known as the "Great Wave."

Saturday Night: Play Ball!

You can’t come to Boston and NOT visit the historic Fenway Park! Fenway is the oldest active park in Major League Baseball. It was built in 1912 (two years before Wrigley Field) and expanded/renovated four times (the latest in 2017). Because of its historic nature and the neighborhood that has built up around it, there isn’t really anywhere else for Fenway to expand. Because of this, the park has odd…well, “unique”…design features like The Triangle, Pesky’s Pole, and the famed Green Monster. Plus, the Red Sox are traditionally a good team, so chances are good that you’ll be cheering on a winning team!

Fenway

If baseball isn’t for you, head over to South Boston for a delightful dinner at Lincoln Tavern & Restaurant. This classic American tavern has upscale faire like woodfired pizzas and wood-grilled entrees. The open-air brick-and-wood interior is both modern and nostalgic, particularly the massive wood-paneled bar. West Broadway is a happening stretch of road lined with restaurants, bars, and shops, so there are plenty of choices if something else strikes your fancy.

Sunday Morning & Afternoon: Crossing the Charles

You caught me. Cambridge is technically a different city from Boston. But after two days, you’re more familiar with the city’s subway system, so hop off the train at Harvard Square. Home to Harvard and MIT, Cambridge is a true college town. Take some time to window-shop before exploring the prestigious Harvard campus, either via guided tour or on your own. Cambridge is full of museums, such as the Harvard Museum of Natural History, along with countless cute stores.

If you want the best hamburger of your life, head over Mr. Bartley’s Gourmet Burgers for lunch. This famous hole-in-the-wall has served hungry celebs and students alike since 1960; everyone from Johnny Cash to B.J. Novak has visited this humble burger joint. Their punny, famous burgers are named after local jokes and an array of famous people: the Snoop Dogg, for example, is topped with bacon and “smoked” ghost pepper jack cheese. The Beyoncé is “deliciously hot” with Cajun flavor. I ordered the Bill Clinton, which was covered in southern barbecue sauce and white American cheese. And don’t worry, Hillary fans. She has a sandwich of her own.

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