Boston is a city worth stopping by for its history, notable higher educational institutions and beautiful outdoor spaces. It’s a city that is easy to get around without a car and is easily walkable in most parts where you can effortlessly go from neighborhood to neighborhood. Two days is enough time to get a solid introduction to the city and its highlights. Here is a list of things to do to fill a Boston itinerary for 2 days.
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Located in the Northeastern corner of the country, Boston gets its share of four seasons. Winter is not the ideal time to come unless you don’t mind freezing temperatures and the occasional snow storm where you are stuck inside. Summertime is when the city comes alive and there are plenty of outdoor activities to enjoy, though it can get quite humid and hot. That being said the best time to come is during late spring to see the city in full bloom or in mid-late autumn when the fall foliage is at its peak.
Getting Around Boston
Boston has the MBTA, an excellent public transportation system, including the T, a wide-reaching subway. If you want to go on day trips to Martha’s Vineyard, Cape Cod, or Salem, there are always buses/ferries/commuter rails that can easily take you to where you need to be. Renting a car can be a lot more hassle than it’s worth, since parking can be difficult and city navigation can be confusing for visitors.
Boston Public Library
As one of the oldest and largest libraries in the U.S., the BPL is a great place to wander around for an hour or two to admire the beautiful interior and exterior. Make sure to stop by Bates Hall (aka the large study room with the sea of green lamps) and the courtyard that is perfect for getting a bit of fresh air in one of the city’s most stunning outside spaces.
One of the main public squares in the city that is located in the Back Bay and has several significant buildings worth checking out including the Trinity Church, Boston Public Library, the John Hancock Tower, and the Old South Church. It’s located right next to the picturesque Newbury Street and the upscale Copley and Prudential malls as well.
There’s a lot of historical sites downtown including The Old State House, one of the oldest buildings in the country, the Granary Bury Ground (the final resting place of famous figures like Samuel Adams), Quincy Market, and Faneuil Hall. Make sure to check out the Brattle Book Shop, which features rows of books in an alley and features rare and used books.
Boston Public Gardens
Boston Public Gardens, has always been my favorite downtown park, since it’s both calmer and prettier than the adjacent Boston Commons. I love how it’s a serene outdoor space literally in the middle of the city. The last time I was there one couple was taking their wedding photos, and they complemented the scenery perfectly amid the weeping willows, the pond, and the downtown skyline in the distance. The Make Way For Ducklings statue is also located in this park.
From the Public Gardens, it’s a quick walk to Beacon Hill, which boasts beautiful historical homes and narrow cobblestone streets. Spend a few hours wandering around the brick-lined streets just soaking it all in and watching residents go about their daily lives. Make sure to stop by Acorn Street, the popular sloped side street and the nearby gold-domed Massachusetts State House, where you can take a guided or self-guided tour on the weekdays. The Charles River Esplanade is also nearby if you fancy a stroll along the water.
Isabella Gardner Museum
This former home feels like you’re inside a painting in the garden courtyard and it’s so captivating. I love also how you can view the garden from the various levels within the home. The art exhibits in the various rooms are also very interesting, including a restoration of a sarcophagus that was taking place in the middle of the garden. The surrounding area is also nice to walk around and explore and you can easily walk through the Back Bay Fens to Fenway Park or walk down street to the excellent Museum of Fine Art if you feel in a museum mood.
It never gets old walking through Harvard Yard, especially in autumn when it’s ablaze with color against the brick buildings. You can wander around on your own, but there is also a great Cambridge tour led by Free Tours by Foot which is pay-as-you-wish, and gives you an informative tour of the campus and the surrounding area. Make sure to stop by Harvard Book Store in Harvard Square to browse the impressive multi-level collection of books. Note that if you’re looking for Harvard University merchandise that it’s sold across the street.
This innovative school should definitely be on your itinerary, where you can spend an hour or two wandering the expansive campus. If you go when classes are still in session, it’s fun to roam the halls amid the student shuffle. Make sure to stop by the Great Dome over Building 10 and the eccentric Stata Center (can’t miss it with its odd angles) where A.I. fittingly has its labs.
Take a detour across the Charles River, back to Boston via the Harvard Bridge, with the ideal time during sunset with all the evening runners. With the MIT sailboats drifting on the water, the greenery of the Esplanade around the edges and the lights of downtown Boston in the distance, it’s hard to find a better view to end the day with. The Harvard Bridge is located right next to the front of MIT and conveniently connects with Back Bay.
After crossing the Harvard Bridge, make your way through the tree-lined streets of Back Bay and make your way down Commonwealth Avenue. Walk down until you hit Dartmouth Street and turn right, and a few blocks later you should be at Copley Square, where you can catch the T to the North End (North Station, Lechmere bound).
This is Boston’s oldest neighborhoods, and is worth stopping by to spend a few hours taking in historical landmarks like the Paul Revere house. A large part of the Freedom Trail also winds its way through the streets. Grab dinner at Regina Pizzera and then head over to Hanover Street, where you grab a cannoli or two from Mike’s Pastry or Modern Pastry across the street (which tends to be less of a mob scene.
Related: Where to Eat in Boston
Where to Stay in Boston
Boston is an easy city to navigate with public transportation and your own two feet, but it’s always good to stay somewhere central like Back Bay, which is one of the city’s most scenic neighborhoods with Newbury Street and Copley Square. Hotel rates can be pricey in this area, but there are some excellent mid-range options available as well.
This South End boutique hotel is a great value for the central location and comfortable rooms that feature quirky touches (think lots of pineapple decor) and beds with double duvet European bedding (think clouds). Amenities include beach cruisers, and the Trophy Room, a beloved local restaurant with a full bar. Copley Square and Newbury Street are a 10-minute walk away.
Located directly on Newbury Street, this hotel gives you a feel of what it would be like to be a local living in the historically beautiful Back Bay neighborhood. Some of the city’s best restaurants are a quick walk from the hotel, as well as La Voille, an excellent restaurant located in the hotel’s ground floor. A complementary hot breakfast is included. Copley station is only a short walk away.
This four-star hotel is all about location, being centrally located in Back Bay, just a few blocks from Boston Public Garden, Boston Common, Copley Square, and Newbury Street. The interior is stunning, with 2 restaurants and 3 bars on property, as well as an impressive fitness center that puts those dingy hotel gyms to shame. A subway station is conveniently just across the street.
Photo source: North End