Weekend In Boston Massachusetts (Fun 2-Day Itinerary!)

Boston is best known for its deep American history, delicious food, passion for sports, and a truly unique accent. This relatively small, walkable city makes for a perfect quick weekend getaway.

I visited family in Boston in early summer, during a 9 Day Southern New England Road Trip. The city was smaller than I imagined, and I was therefore surprised how much we were able to see in just two days. 

Read on for my exact weekend in Boston itinerary! 

Things To Do During Your Weekend In Boston 

Day 1 In Boston

Be warned, this is a large itinerary for just one day, we walked a lot. If you have a long weekend in Boston, split Day 1 into two days. This will give you more time to really explore each neighborhood. 

Harvard & Cambridge 

The original founders of Boston placed high value on education, a sentiment which is still apparent today. There are so many impressive universities worth visiting while in town, one of the most famous of which is Harvard University.

Harvard offers free in-person tours and a self guided tour through their app. You can find information regarding both at Harvard Tours. 

We took a stroll through Harvard Yard, which is the center point of the main campus. 

Following our quick Harvard tour, we followed the Charles River for a nice walk.

From the river we eventually wandered into Mid-Cambridge which is a popular neighborhood with picturesque homes as well as quality dining and shopping.

Popular Universities To Visit In Boston

The city of Boston has dozens of universities all within a small radius, some of the most popular to visit are:

• Harvard
• MIT (Massachusetts Institute of Technology)
• Boston College 
• Northeastern University 

Charles River Esplanade 

After about 2 hours exploring Cambridge we hopped on the subway and headed back towards downtown Boston.

Upon arrival downtown we took a walk through Charles River Esplanade park in Back Bay.

I loved this park and think it’s absolutely worth a stroll if you’re in Boston on a warm, sunny day. Here you can sunbathe on the docks with locals, kayak, or simply find a shady spot on the bench to enjoy people watching. 

The park even hosts free movie nights and live music.

Beacon Hill 

From the park we followed Charles Street through Beacon Hill, which is a posh neighborhood known for great shopping and dining among picture-perfect townhomes and cobblestone streets.

This is one of the city’s most picturesque neighborhoods, and the only one designated a National Historic Landmark, so it’s definitely worth exploring during your weekend in Boston.

Tip: If you’re looking for a sit down lunch this is a great neighborhood to grab a bite.

Acorn Street

While in the area, be sure to check out Acorn Street which is a charming cobblestone alley dubbed the most photographed street in the United States.

The alley has features which date back to the 17 and 1800’s making it feel as though you’ve stepped back in time.

Black Heritage Trail

A walking tour of the Black Heritage Trail is another popular thing to do in Beacon Hill.

The trail shows community buildings and homes occupied by the Black community living in Beacon Hill before, during, and after the Civil War.

Community members advocated the abolishment of slavery, worked to equalize rights and education opportunities, and cared for freedom seekers along the Underground Railroad.

The National Park Service offers free walking tours of the Black Heritage Trail, reservations need to be made in advance at NPS Black Heritage Trail Tour.

Public Garden & Boston Common

Public Garden and Boston Common are parks flanking Charles Street on the edge of Beacon Hill. 

Both parks are worth exploring. They’re characterized by beautiful, mature trees, thoughtful gardens, and of course, swan boats.

The Public Garden was the United States first public Botanic Garden built in 1837. Today visitors still enjoy strolling through the park which showcases over 80 species of plants. This is where you’ll find the swan boats, which are a 100+ year old, family-owned operation much-loved by the city. 

Boston Common is the larger of the two parks, established in 1634, the 50-acre park is the oldest public recreation area in the country. The site has held many public gatherings — including protests and debates — over the past 400 years.

This green space is where a rally was held commemorating the end of the Revolutionary War and has since seen speeches from notable figures such as Martin Luther King Jr. and Pope John Paul II, to name just a few.

Tip: If you wish to visit the Cheer’s Bar, made famous by the 80’s sitcom Cheers, it’s located on Beacon Street, overlooking Public Garden.

You May Also Like: The Best Free Things To Do In Boston

Freedom Trail

Boston Common is the starting point of the highly popular Freedom Trail, which is a 2.5 mile urban trail connecting 16 sites significant in US history.

If you wish to join a tour, this is where you’d start. Purchase a guided tour or follow the trail to see the historical sites for yourself (the latter of which is what we did!). 

A few highlights along the Freedom Trail include:

• Boston Common
• Massachusetts State House
• Old State House
• Granary Burying Ground
• Park Street Church
• Old South Meeting House

Faneuil Hall Marketplace

Following our time in the park, we made our way through City Hall Plaza and over to Faneuil Marketplace which has been one of the Boston’s focal points for almost 300 years. 

The marketplace is made up of four buildings, three of which — North Market, South Market, and Quincy Market — are collectively referred to as “Quincy Market.”

The Quincy Market dates back to the 1800’s and is lined with local dining options ranging from quick bites to savory sweets. Just outside the market are additional food and boutique stalls as well as popular shopping retailers.

If you’re hungry for a quick bite this a great place to stop, although it does get very crowded.

The fourth building, Faneuil Hall, is where America’s first Town Meeting was held and was an important gathering spot during the American Revolution. 

Faneuil Hall is often referred to as “the home of free speech” and the “Cradle of Liberty.” The building was donated to the city in 1742 by Peter Faneuil, a wealthy slave owner and trader. The irony of which is apparent to many, there have been many discussions in recent years regarding a necessary name change for the historic building and marketplace. 

Additional Things To Do Near Faneuil Marketplace

The area around the Faneuil Hall Marketplace is a big tourist hub, so you’ll find lots of attractions in this area.

If you have time, consider checking out one of these nearby attractions:

• The New England Holocaust Memorial
• Haymarket
• Shopping on Newbury Street
• Boston Public Library
• Trinity Church
• Watch the street performers
• Government Center & City Hall Plaza
• Boston Public Market

Visit Boston’s North End

The North End is a hodgepodge of narrow streets winding through some of the city’s oldest buildings. The area, also referred to as Little Italy, was once physically divided from the rest of Boston due to the construction of I-93. 

The physical rift left the North End behind, with residents continuing on without interference from the modernizing and growing downtown area. 

The obstructing portion of the highway was moved underground in the early 2000’s, reconnecting again the North End to the rest of Boston. Traveling between the two is almost like traversing into a new city — with clear differences still easily noticeable.  

When I imagined Boston, this is what I had in my mind. Narrow sidewalks with outdoor cafe seating, delis and bakeries which have been around for generations, it’s very charming and was one of my favorite places to visit in Boston.  

Tip: If you’re planning to dine or shop here, be sure to bring cash.

Things To Do In Boston’s North End

There’s quite a bit to do in the North End, but the area is small, so it’s easy to get from point to point. These are a few of the highlights:

• Admire the architecture. 
• Walk The Paul Revere Mall.
• See Old North Church – a historic, American Revolution site.
• Eat! 
• See the Paul Revere House – a historic site and one of the oldest homes in Boston.
• Visit the Skinny House.

Who is Paul Revere? Paul Revere is famous for his midnight ride from Boston to Lexington, alerting the Colonists of oncoming British attack. This played an important role in the Colonists victory in later battles. Today Paul Revere a symbol of bravery and the start of the Revolutionary War, which eventually led to the United States’ independence.  

Walk Through Christopher Columbus Waterfront Park 

We made a brief stop in this waterfront park on our way to the Seaport District.

It’s just a short walk from the North End and a fun spot to watch boats along the harbor. The area was a former shipping port and still holds onto that feeling today. 

Also, for those interested in visiting the New England Aquarium, this is where you’d do so.

Tip: This is the perfect place to enjoy a picnic or let the kids run around on the playground.

Explore The Seaport District 

Our final stop of the day was the Seaport District. This is one of the most modern sections of Boston thanks to redevelopment over the past few decades. 

The area is known for contemporary art as well as lively dining and nightlife. From a historic standpoint, it’s known as the approximate location of the Boston Tea Party. 

The area offers excellent views of downtown Boston, so I recommend at least taking the short walk across the Evelyn Moakley Bridge, from here take in the skyline views from the Boston Harborwalk. 

Tip: Grab dinner from one of the popular waterfront restaurants in the area. We had dinner at The Barking Crab.

We were running out of daylight at this point, but if you have time, consider checking out attractions like the Boston Tea Party Ships & Museum or the Institute of Contemporary Art.

Day 2 In Boston

Day Trip To Salem

Salem, located about 20 miles from Boston, is a town famous thanks to an odd yearlong stretch in the late 1600’s when the town successfully tried and hanged 19 citizens for practicing witchcraft.

Proof of said witchcraft is shaky, to say the least, and the whole thing sounds like a bad case of hearsay at the price of a few unlucky souls. 

During our day trip to Salem we viewed famous sites such as the home of the infamous Judge Hathorne, a vocal leader during the trials, as well as the House of the Seven Gables, and Salem Witch Trials Memorial. 

We also thoroughly enjoyed the many kitschy, but fun, witch-themed shops throughout town. This was definitely my favorite part of our weekend in Boston!

Visit The Hocus Pocus Filming Sites In Salem 

Of course, as a 90’s kid, I had to see the filming sites of Disney’s Hocus Pocus! Below are the sites we saw in Salem:

• Max & Dani’s House
• Allison’s House
• Town Hall
• The School 
• Thackery Binx’s House & Old Salem Village
• Old Burial Hill Cemetery (in Marblehead, MA)

For my full itinerary, check out this Day Trip To Salem, MA guide.

Getting To Salem From Boston 

Train

Salem is accessible from the subway and takes about 30 minutes each direction. Depart Boston’s North Station and stop at Salem. It costs $2.40 each time you enter the subway.

Ferry

There’s also a fast ferry which costs about $42 in each direction and takes 1 to 1.5 hours each way. Schedules and ticketing can be purchased through the Salem Ferry. 

Catch A Game At Fenway Park

Back in the city, we headed to Fenway Park for our final night in Boston.

Home to the Boston Red Sox since 1912, Fenway Park is the oldest MLB stadium still in use today. The beloved park is a must-see, baseball fan or not.

I love baseball and enjoy the history and nostalgia which accompanies a stadium such as Fenway. 

We were able to catch a game while the Sox were in town and sat in the rowdy bleachers (which I highly recommend!). During the game we saw three homers fly over the green monster, drank a few beers, and watched the Sox win. It was a perfect evening!

If you’re up for pre or post game libations, there are a couple bars in the area. We went to Bullpen Kitchen + Tap before the game.

Not visiting during baseball season? Stadium tours are available year-round: Fenway Park Tours.

Boston Sports

Boston is a huge sports town, so whether or not you’re visiting during baseball season, there’s a good chance you can still catch an event.

Boston is home to the NBA’s Boston Celtics and NHL’s Boston Bruins, both of whom play at TD Garden. Plus the NFL’s New England Patriots who play at Gillette Stadium, about 30 miles outside the city.

Getting Around Boston

The best way to get around Boston is by foot, bike, subway, or ride share app / taxi. 

Boston’s Subway System

Boston’s subway system is called the T and it will get you all around the Boston area without having to deal with traffic.

It costs $2.40 each time you enter the subway, from there you can make as many transfers as you need. As long as you don’t leave the subway, you aren’t charged again. 

Cards can be purchased at subway entrances or use the mTicket app. 

For those in town longer than a weekend they have a 7 day pass for about $22. 

Do You Need A Car In Boston?

Definitely not, the city is relatively small and easy to navigate by foot or using public transportation. 

Boston’s roadways are a bit of a nightmare, the city was built in the 1600’s after all, I do not recommend driving here. 

If you’re arriving by car, park at your hotel or use SpotHero to find a relatively affordable parking garage.

Where To Stay In Boston 

If only spending 2 days in Boston, it’s important to stay somewhere centrally located. Check out the following options.

• Harborside Inn Of Boston
• The Bostonian Boston
• Courtyard Boston Downtown (this is where we stayed)
• Boston Harbor Hotel
• Moxy Boston Downtown
• Revere Hotel Boston Common
• Sonder 907 Main (Cambridge)

Getting To Boston

Fly

Boston Logan International Airport is just 3.5 miles (15 minutes) from downtown. From here either get a ride or take the free Silver Line into South Station.

Looking for cheap flights? Be sure to sign up for Going (formerly Scott’s Cheap Flights) to get cheap flight alerts delivered right to your inbox. It’s a free service I’ve used for years and couldn’t recommend more. 

Train

The Amtrak train drops off visitors in South Station, located the heart of downtown Boston, making it extremely easy to visit by train! Ride directly from New York City, Portland, or many many other Amtrak stations in the northeast for a quick and convenient getaway.

Is 2 Days In Boston Enough?

3 – 4 days in Boston is ideal, however, in 2 days you can see many of the city’s highlights. 

With only a weekend in Boston be sure to have a good plan regarding what you’d like to see, and stay somewhere central so you’re not wasting time getting around.

As you can see, there’s so much to do with a weekend in Boston! I hope you find this guide helpful and happy vacation planning!

Any questions or additional ideas? Please leave a comment below or reach out on social media.

Looking for more ideas? Check out my additional Boston and Massachusetts guides below.

More Information For Your Boston Vacation:

• Free Things To Do In Boston, MA

More Information For Your Massachusetts Vacation:

• Cape Cod & The Islands Guides
• Plymouth, Massachusetts Guides
• Salem, Massachusetts Guides

More Information For Your New England Vacation:

• Connecticut Guides
• New Hampshire Guides
• Rhode Island Guides
• Vermont Guides
• Southern New England Road Trip: 9-Day Itinerary