Weekend in Boston: The Best of Boston 2-Day Itinerary (2024)
Planning a weekend in Boston?
Then you’ve come to the right place.
Boston is a vibrant city with the perfect mix of charming neighborhoods, fun activities, and interesting history. If you’re interested in learning about the early days of the United States, then you won’t find a better destination than Boston (although Philadelphia comes a close second!).
When I lived in New York I took many weekend trips to Boston to visit family, and I loved exploring this beautiful city. With only 2 days in Boston, you can see many of the city’s highlights and get a taste of Beantown that will make you want to come back for more.
So if you’re ready to plan the ultimate weekend in Boston, then read on for the perfect Boston weekend itinerary.
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Weekend in Boston: Itinerary at a Glance
Day 1:
- Historic Boston walking tour
- Freedom Trail
- Boston Public Market
- Harbour boat cruise
- Dinner in Fenway
Day 2:
- JFK Presidential Library
- Boston’s South End
Day 1 in Boston
Morning
Begin your Boston weekend trip by walking the Freedom Trail (or part of it). I’m a huge fan of walking tours, and on my first trip to Boston, we started the trip with a historic walking tour of the city.
The Freedom Trail is a 2.5-mile walk that passes 16 colonial and Revolutionary War-era sites. The trail is marked with a line of red bricks that runs along the ground, leading you from site to site.
On the walking tour, you’ll see many of the most famous historical sites along the Freedom Trail. I loved the orientation provided by the tour guide, which gave a lot of information and context for the importance of these sights.
Boston Common
The Freedom Trail begins at Boston Common, America’s oldest public park (est. 1634). While originally used for grazing cattle, over the years Boston Common has been a camp for British soldiers, the site of public hangings and riots, and is now a National Historic Landmark.
In more recent history, the northeast end of The Common is where you can find the Park Street station, one of the oldest subway stations in the United States. Boston opened their underground system, the “T”, in 1897, beating New York City to the first subway system in the country.
Directly across from Park Street station is Park Street Church. Built in 1809, the church was the site of William Lloyd Garrison’s first major public speech against slavery. Supposedly, the church basement was used by the rebels to store gunpowder during the Revolutionary War.
Massachusetts State House
Following the red bricks, continue to the Massachusetts State House.
Built in 1798, the building houses the Massachusetts state legislature and the offices of the governor. As far as state house buildings go, this is one of the most stunning I’ve seen, with a gold dome covered with 23-carat gold.
The State House is open to visitors on weekdays, but unfortunately, if you’re coming to Boston on the weekend you can only admire the building from the outside.
Granary Burying Ground
Next, head to the Granary Burying Ground.
Established in 1660, this cemetery is the final resting place of many notable early Americans. Some of the big names buried here are Samuel Adams, John Hancock, and Robert Treat Paine, all signers of the Declaration of Independence.
Other persons of note buried here are Paul Revere and Mary Goose (aka Mother Goose).
Old South Meeting House
From the graveyard, continue on to the Old South Meeting House, a long-term site of free speech and dissent.
Erected in 1729 as a Puritan meeting house, Old South was the site of many meetings leading up to the American Revolution. In fact, on December 16, 1773, sparked by the Tea Act of 1773, approximately 5,000 men met in the hall to debate taxation by the British. The aftermath of this meeting resulted in what we now call the Boston Tea Party in which The Sons of Liberty, led by Samuel Adams, boarded three British vessels docked in the harbor and dumped 342 chests of tea into the water.
The meetings that occurred in Old South, the discussions that took place, and the resulting actions, set off a chain of events that ultimately sparked the American Revolution.
If you’re on a guided tour you may not have time to enter the meeting house, but I highly suggest you return later to see the inside.
Inside is a small exhibit on the role that the Old South Meeting House played in the American Revolution. Touring the interior of the building takes 30 minutes to 1 hour.
Old Corner Bookstore
The Old Corner Bookstore is downtown Boston’s oldest commercial building. Unfortunately, the building is now home to a Chipotle restaurant, so unless you’re hungry and in the mood for some Mexican-style fast-casual, it’s time to move on.
Old State House and the site of the Boston Massacre
The Old State House is the oldest surviving public house in Boston.
If you have the time and interest, enter the building for another small museum. While the museum is worth visiting, it’s not as good as the one at the Old South Meeting House. If you’re strapped for time, I would skip this one.
Around the back of the Old State House is the site of the Boston Massacre. A plaque on the ground marks where the massacre occurred, but the exact spot is actually a few feet away in the middle of the intersection.
The five-pointed star at the center of the plaque represents the five people killed during the massacre, and the six bricks surrounding the star represent the six injured.
The Boston Massacre was one of the turning points leading to the Revolutionary War. The events that took place here were sensationalized and spread across the colonies.
In fact, Paul Revere (heard of him and his midnight ride?) produced a well-known and exaggerated engraving depicting the events of the massacre, which showed the British soldiers firing on innocent and defenseless colonists. This engraving was widely distributed throughout the city and helped fan the flames of revolution.
Faneuil Hall
Conclude your walk of the Freedom Trail at Faneuil Hall: home of free speech and “Cradle of Liberty.”
For the past 275 years, Faneuil Hall has hosted meetings, protests, and debates on topics ranging from abolition to women’s suffrage to unions.
As one of Boston’s many indoor activities, you can enjoy Faneuil Hall no matter the weather. I highly recommend going inside and viewing the hall (admission is free), and while you’re there try to catch a 20-minute ranger talk on the history and legacy of the space.
Faneuil Hall also houses the visitor center for the National Park Service, so make sure to stamp your National Park passport!
Afternoon
If at this point you need a break from all the walking, I suggest heading across the street to the Boston Public Market.
This food hall contains many different dining options, from not-so-traditional Jewish cuisine (try the Shaka-latkes at Inna’s Kitchen) and smoked fish stalls to more common fare like pasta and sandwiches.
For dessert, try a popover from The Popover Lady, or a hot apple cider donut from Red Apple Farm.
While there are many more must-see stops along Boston’s Freedom Trail, you probably won’t have time to see them all with only two days in Boston.
After enjoying lunch at Boston Public Market, take to the seas on a Boston Harbor cruise.
We did this during our weekend trip to Boston and absolutely loved it. From the boat, we were able to take in the city skyline and harbor Islands. We ordered some beers on board and just relaxed and took in the views — the perfect thing after walking all morning!
Book your Boston Harbor Cruise today!
Evening
End your first day in Boston with dinner in the Fenway neighborhood.
Better yet, if you’re visiting Boston during baseball season, why not catch a game at this iconic ballpark? It’s one of the oldest ballparks in the United States and a pilgrimage site for avid baseball fans.
If you’re not coming to Boston during baseball season you can still take a tour of the park. This Fenway Park tour is a great way to learn about the history of the park, the game, and the Red Sox.
Day 2 in Boston
Morning
Moving away from Boston’s Revolutionary War history, let’s jump to the 21st century by visiting the John F. Kennedy Presidential Library.
The library is housed in a stunning building designed by architect I.M. Pei, with a wall of windows nine stories high looking out over the harbor.
The museum takes around two hours to see properly and includes an excellent 20-minute video introduction on JFK’s early life and education.
The majority of the museum focuses on the Cold War and Cuban Missile Crisis, with other topics including his early career as Massachusetts Senator and his presidential race against Nixon.
I came away from the museum with a better appreciation of JFK’s political appeal and a positive impression of him as a historian and politician. The content in the museum intrigued me and made me want to go out and learn more about JFK and his short time as president.
Afternoon
Depending on how you arrived for your weekend in Boston and how far you have to travel, you may need to head to the airport or Amtrak station and head back home.
If you do have some extra time in Boston, then head to the South End neighborhood for the afternoon.
Boston’s South End is best known for its beautiful Victorian row houses. The neighborhood is full of delicious restaurants and intriguing art galleries. It’s perfect for grabbing some lunch and wandering through the charming city streets. Some popular eateries are Elephant Walk, offering Cambodian-French fusion, and Ilona, offering fresh Greek and Mediterranean flavors.
More Than 2 Days in Boston? Additional Things to Do in Boston
Coming to Boston for a long weekend trip and have more than two days to explore the city? Here are some additional highlights to add to your Boston city break itinerary:
- Museum of Fine Arts, Boston – Housing everything from ancient Egyptian to contemporary American, this is Boston’s premier art museum.
- Isabella Stewart Gardner Museum – Art with a side of mystery. This museum, built to evoke the feeling of a Venetian Palace, was the sight of a high-profile art theft. Come for the art, stay for the intrigue.
- New England Aquarium – A wonderful aquarium featuring aquatic species from around the world.
- USS Constitution Museum – Tour the world’s oldest naval warship still afloat, then head to the adjacent museum to learn about the history and life of sailors in the late 1700s.
- Bunker Hill Museum and Monument – The museum details early battles of the Revolutionary War, including a detailed diorama. Head to the top of the monument for panoramic views.
- Paul Revere House – Tour the home of the famed Revolutionary War hero, most famous for riding at midnight.
- Boston Tea Party Ships and Museum – This interactive museum brings the experience of the Boston Tea Party alive through reenactments. This is a great stop for families who want to bring history alive for their kids.
- Boston Public Library (Central Library) – Often touted as the most beautiful library in America, this branch of the local public library system is well worth a visit. Although not a museum, the library is full of paintings, tapestries, and beautiful architectural elements.
Is a Weekend in Boston Enough?
No, a weekend in Boston is not enough, but it’s a great start for getting an introduction to the city. Even though I’ve visited Boston many times, there are still museums and neighborhoods I’ve yet to explore. While a weekend is a good start, Boston is a city you’ll want to return to again and again.
How to Get to Boston
By Air
The city of Boston is served by Boston Logan International Airport (BOS). The airport is only 2.5 miles outside the city center. While traffic will dictate how long it takes to travel from the airport to the city, a taxi ride typically takes around 10-15 minutes.
By Train
Boston’s South Station Amtrak terminal is located just south of the downtown area, making it a convenient and economical way to get into the city. If you’re traveling from other East Coast cities, like New York, then Amtrak is one of the best options for traveling to Boston for a weekend getaway.
By Car
I don’t recommend driving to Boston for the weekend due to the traffic and hassle of having a car in the city. If you do drive there, take Interstate 93 or 90, which go directly through the city center.
By Bus
Bus is a popular mode of transportation to and from Boston, especially if you’re traveling from another city in New England. The bus terminal is located on Atlantic Avenue, next to South Station.
How to Get Around Boston
Public Transportation
Boston’s public transit, known locally as the “T,” is a convenient and affordable way to navigate the city. The stations are marked prominently with a “T” symbol, making them easy to locate while in the city.
Within the city, the subway connects Boston’s top attractions. Areas not connected to the subway are linked via extensive bus routes. Passes can be purchased for single or multiple rides at station vending machines.
Walking
Boston is a compact city, so you’ll be able to get to most places by walking. Walking is also the best way to appreciate the local neighborhoods and to find hidden gems. Boston also has many parks to explore, as well as picturesque waterfront strolls.
Biking
Consider renting a bike as another way to explore Boston. Biking lets you cover more ground than walking, while also giving you the flexibility to hop off and explore at your leisure.
Taxis & Ride Share
Taxis and rideshares are readily available and easy to hail. These can be especially good options if you’re out after hours and the T has stopped operating.
Where to Stay in Boston
Hilton Boston Park Plaza
This beautiful hotel is just a three-minute walk from Boston Public Garden. While rooms are on the small side, the location is within walking distance of many top sights and great eateries.
Courtyard by Marriott Boston Downtown/North Station
An affordable hotel in a central location, the Courtyard by Marriott Boston Downtown is within walking distance of the North End sights. This downtown Boston hotel is also adjacent to the T, making it convenient to navigate from here to other parts of the city. While rooms are a bit spartan, they are clean and well-kept.
InterContinental Boston
Luxury hotel with large, comfortable rooms within walking distance of many locations. The hotel has excellent city views, and its location along the Boston waterfront makes it convenient for boat tours.
FAQ: Spending a Weekend in Boston
Absolutely! Boston has a rich history, a vibrant cultural scene, and charming neighborhoods, making it a great destination for a weekend getaway.
Yes, two days can give you a good taste of Boston’s main attractions and neighborhoods. You won’t see everything, but you can cover key landmarks and get a feel for the city’s vibe during that time.
Three days will allow you to see more of Boston, but it still may not be enough to visit all the city’s highlights. With 3 days in Boston, you can visit major attractions, explore different neighborhoods, and visit some sights further afield.
Yes, you can get around Boston without a car. In fact, public transit and walking are the best ways to get around Boston as they help you avoid traffic and the hassles of finding parking in the city.
Absolutely, Boston is worth a visit! Whether you’re into historical sites, museums, sports, or just soaking in the city vibe, there’s something for everyone in Boston.
September and October are often considered the best time to visit Boston. The weather during these months is pleasant, with comfortable temperatures and fewer crowds compared to the peak summer months. Plus, you’ll catch the beautiful fall foliage if you visit later in October.
Final Thoughts: Weekend in Boston Itinerary
Boston is an incredible city. It has history, great food, cute neighborhoods, and incredible art museums. A weekend in Boston offers only a snapshot of the city’s charm and diversity. While two days won’t cover everything, it’s enough time to see the best of Boston and get a feel for this vibrant city.
I hope this 2 day Boston itinerary helps you plan your perfect weekend in Boston. Enjoy your weekend trip!
Had fun reading this post… I now want an apple cider donut.
Looking forward to reading more!
-Shannon