What’s the fun in visiting a city only to do things that you can do anywhere else? My goal when exploring a new place is to immerse myself in activities that accurately depict that city. Boston is one of those places where it’s easy to find activities that are well…uniquely Boston. Full of interesting things like world class museums, quaint neighborhoods, plus tasty food and drink, you’ll find plenty of Bostony things to do in Boston.
Table of Contents Show
- Top Things to do in Boston
- Discover Boston on a Walking Tour
- Ride a Trolley
- Indulge in a Boston Cream Pie
- Go Sailing in Boston Harbor
- Sip Beer at the Sam Adams Brewery Tour
- Head to College for a Day at Harvard
- Eat Cannoli at Mike’s Pastry Shop
- Sample Street Food on at Quincy Market
- See Works of Art at Isabella Stewart Gardner Museum
- Get Historical on the Famous Freedom Trail
- Read a Book at the Boston Public Library
- Smell the Flowers at the Boston Public Garden
- Stroll Through Beautiful Beacon Hill
- Be a Star For the Day on a Movie Tour
- Even More Things to do in Boston
- Where to Stay in Boston
- When is the Best Time to Visit Boston
- Plan a Visit to Boston
Top Things to do in Boston
Boston, the capital of the state of Massachusetts, has a lot to offer. The history here alone makes it worth visiting but throw in the beautiful waterfront location – not to mention the sports – and fascinating surrounding areas and you’ve got a city worthy of a visit on its own or that can be included in a road trip to visit some of those other places. In fact, my first introduction to Boston was a Boston to Bar Harbor road trip with my daughter.
Inside the city proper, and with possibly a side trip to Cambridge, there’s so many interesting and different things to do in Boston as you learn about it’s history and maybe eat some lobster. Here’s just a few suggestions to get you started.
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Discover Boston on a Walking Tour
As a first-time or experienced visitor to Boston, one of the best things you can do is take a tour to learn about the city and have fun while you’re doing it. The Freedom Trail walking tours are a great choice because they showcase a collection of historical sites from 17th – 19th century Boston while telling the story of the American Revolution.
Depending on who you book your tour with, you can choose from a variety of tour options including Walk into History, Revolutionary Women, African-American Patriots, Historic Pub Crawl and more. Most walking tours cover a distance of one mile or less and take 90 minutes. The best part is – they are led by a tour guide in an 18th-century costume!
Be sure to leave some time after your tour for a more in-depth visit to some of your favorite attractions from the tour. You can also stay at the Aloft Boston Seaport hotel for lodging convenient to the airport, convention center and the redeveloped South Boston Waterfront area with restaurants and bars.
Recommended by Jenny from Global Game Plan
- Boston Town Crier
- 139 Tremont St, Boston, MA 02111, USA
Ride a Trolley
To switch it up, instead of walking the streets of Boston take the trolley ride through the city. The Old Town Trolley offers a variety of tours and packages throughout Boston. This mode of getting around is especially good for first-time visitors and is easier for families with small children.
You can choose from one or two day hop on hop off, city tours that includes all the major areas like Downtown, Beacon Hill, Back Bay, the Theater District, and the Waterfront District or book a themed tour. There’s a spooky Ghosts and Gravestones tour and a Boston Tea Party Ships and Museum tour available plus other seasonal offerings for holidays and in summer.
The trolley tours are a convenient and affordable way to see the city when you don’t have much time or don’t have a car.
- Old Town Trolley
- 200 Atlantic Ave, Boston, MA 02110
- parking available nearby
Indulge in a Boston Cream Pie
It wouldn’t be a trip to Boston without indulging in a dessert named for the city itself. It’s believed that this dessert, really more cake than pie, was first made in 1856 by Armenian-French chef M. Sanzian at the Parker House Hotel in Boston.
The cake has two layers of sponge cake filled with gooey custard and brushed with a rum syrup. Then toasted sliced almonds are overlaid on the sides and the top is covered with pliable chocolate fondant. According to Wiki – other custard cakes may have existed at that time but baking chocolate as a coating was a new process, making it unique and a popular choice on the hotel menu.
Boston Cream Pie can be found all over the city. Of course, you can pay a visit, or stay, at the Omni Parker House Hotel to try the original, still on the menu, or book a Boston food tour that includes a sample this delicacy and other local flavors.
- Omni Parker House
- 60 School St, Boston, MA 02108
Go Sailing in Boston Harbor
Boston Harbor is one of the most beautiful and historic sailing areas in the world. With its strong currents and rich history, the harbor is a popular destination for both experienced and beginner sailors alike. Visitors to the harbor can enjoy stunning views of the city skyline. Standing on the deck of a boat, you can get a sense of just how large and varied the architecture of Boston is.
And, of course, the harbor is a sight to behold, with both massive ships and small boars navigating it simultaneously. Additionally, sails will come with excellent commentary on the harbor’s history making it a great way to learn more while enjoying the cruise!
The harbor is home to a number of different sailing clubs and organizations, making it easy to find a group to sail with. Boats will range from 100-person cruises down to a small boats for just a couple of people allowing you to customize your experience!
Whether you’re looking for an exhilarating experience or a relaxing afternoon on the water, sailing on the Boston Harbor is sure to be a highlight of your trip to Boston. Recommended Tour: We did this one – it was a small 2-4 person boat and we loved it!
Recommended by Kelsea of Out of Office Mindset
Sip Beer at the Sam Adams Brewery Tour
If you love beer, a visit to Samuel Adam’s Brewery is sure to be the highlight of your Boston trip! Not only can you take a tour of their brewhouse, they also offer a wide range of experiences to engage every beer lover out there whether you’re a beginner or bona fide brew master.
They’ve even got a fun tour for the foodies where you can sample their small batch, barrel-aged beers paired with local cheeses. For those wanting something a little extra special, Sam Adams even offers ongoing events like Taproom Trivia every Thursday, beer mixology classes, music bingo and even a speakeasy-style prohibition day celebration!
But, if you’re really looking to be dazzled, try Sam Adam’s VIP experience which takes you into the secret lab in their Nano Brewery where you’ll taste never-before-seen beer and witness the process it takes experiment and select Samuel Adams next superstar beer before it hits the shelves.
And if you happen to come on one of their hoppiest times of year, St. Patrick’s Day, you’ll be treated to the festivities of all festivities, honoring this simple and classic past time. Cheers!
Recommended by Geeves from Real Girl Review
- Samuel Adams Boston Brewery
- 30 Germania St, Boston, MA 02130
Head to College for a Day at Harvard
Harvard University is one of the most prestigious Ivy League colleges in the United States. If you’ve ever dreamed of walking through the campus and seeing it first hand, now’s your chance.
Located right outside of Boston in Cambridge, Harvard University Visitor Center offers a free in-person Historical Tour of Harvard walking tour. This student led tour explores Harvard Yard – the oldest part of the university with some of the most historical points of interest on campus, including the John Harvard statue. However, you might want to think twice before rubbing his golden foot for good luck.
Tours depart from the visitor center which is located at the front desk in the Smith Campus Center and lasts about an hour. Advance registration is required.
In addition to the in-person tours, if you prefer to do a tour on your own, Harvard also has a free mobile app that offers a collection of different self-guided tours focused on the Harvard University experience. This one mile, self-guided tour takes place across fourteen mapped stops on campus and takes about an hour to complete.
- Harvard University Visitor Center
- 1350 Massachusetts Avenue, Cambridge, MA 02138.
Eat Cannoli at Mike’s Pastry Shop
Visit the best Italian bakery in the North End of Boston. Established in 1946, this bakery has stood the test of time and become a can’t-miss place when visiting Boston for the first time. As you walk into the shop, you are greeted by the sights of gorgeous pastries in display cases and the laughter of people enjoying their treats.
Locals and visitors alike will line up on Hanover Street just to purchase a freshly baked cannoli or lobster tail pastry. The lobster tail is the American version of the sfogliatelle ricce. They are a bit larger and filled with choux paste before baking. This causes the pastry to puff up in the oven, and the perfect space to fill a mixture of pastry cream and whipped cream.
For those who are visiting, it’s best to arrive at Mike’s Pastry Shop on foot due to the narrow streets and scarce parking spots. Visitors can exit from the Aquarium Station (Blue Line) or the Haymarket Station (Orange Line) on the MBTA. Mike’s Pastry is less than a minute’s walk from Paul Revere’s House. Other fantastic stops along the way include the Old North Church, The Paul Revere Statue, Faneuil Hall, and the New England Aquarium.
Recommended by Kate from Passports and Playgrounds
- Mike’s Pastry
- 300 Hanover St, Boston, MA 02113
Sample Street Food on at Quincy Market
Quincy Market is one of the most beloved landmarks in Boston, and if you’re looking to get your fill of authentic Bostonian food this is the best place to visit! The market has been serving hungry guests since 1826. The market originally focused on selling fresh produce, but today it’s far more focused on serving up street food of different varieties and fun Boston souvenirs.
Since Quincy Market is on the Freedom Trail and near Faneuil Hall there’s no reason not to add it to your Boston itinerary! With over 50 food vendors to choose from, though, stepping inside Quincy Market can feel quite overwhelming if you don’t have a plan of action.
Top-rated stops at Quincy Market include the Boston and Maine Fish Company, where you’ll get insane hot buttered lobster rolls, and Regina Pizza, where you’ll find huge and delicious slices of pizza with a variety of toppings.
Quincy Market is open Monday-Saturday from 10am-9pm, and on Sundays from noon until 6pm. Entry is free!
Recommended by Ella from Many More Maps
- Quincy Market
- 206 S Market St, Boston, MA 02109
See Works of Art at Isabella Stewart Gardner Museum
This unique museum is a must-see for any art, architecture, or history-lover while in Boston. Not only does it have an impressive collection of European, Asian, and American art, but it was designed in the style of a 15th-century Venetian palace. And it was home to the biggest art heist in modern history.
Isabella Stewart Gardner was an art collector and patron of the arts. After her husband’s passing, she opened the museum to share her collection of paintings, sculptures, furniture, and rare books. Upon her death in 1924, Isabella left the museum for the education and enjoyment of the public forever. Since then, nothing in the galleries had been changed, until March 18, 1990.
That night, two men dressed as police officers tricked the security guards into letting them into the museum. They made off with thirteen works of art, including a Rembrandt and a Vermeer, that would be valued at $500 million today.
Despite hefty reward money, none of the stolen works have ever been recovered. When visiting, you can learn about the heist and see the empty frames that held the art. Plan to spend at least an hour at the museum, ideally two. After seeing the gallery, relax in the peaceful indoor courtyard or grab a bite at the museum’s café.
Fun Fact: Admission is free on your birthday or if your name is Isabella!
Recommended by Laura at Wine Travelista
- Isabella Stewart Gardner Museum
- 25 Evans Way, Boston, MA 02115
Get Historical on the Famous Freedom Trail
If you’re looking for the best things to do in Boston on a weekend getaway in Boston, following the Freedom Trail will deliver you straight to many of them! Boston’s famous Freedom Trail knits together 16 historical attractions relevant to the American Revolution over the course of a 2.5 mile route through the city.
While two of the sites – the Bunker Hill Monument and the USS Constitution – are a bit of a hike from the rest of the attractions, the other 14 sites can be experienced more or less back-to-back.
Top attractions on the Freedom Trail include Old North Church, the Boston Common, the King’s Chapel and Burying Ground, Faneuil Hall, and more. Some stops (like the Paul Revere House) are museums you can go inside, while others (like the Boston Massacre Site) are merely points of interest.
You can easily experience the bulk of the Freedom Trail on one very full sightseeing day in Boston – on a self guided tour – but if you’re particularly interested in learning about 18th century American history, you may want to take a bit longer to explore!
Recommended by Kate from Our Escape Clause
Read a Book at the Boston Public Library
Visiting the Boston Public Library is one of the best things to do in Boston and one of the most outstanding libraries in the United States. According to the library’s website, among other things, the library “was the first large free municipal library in the United States and the first public library to lend books”. It’s a Boston historic cultural institution!
The library is also the second-largest public library in the U.S, right behind the Library of Congress. It’s so large, it contains approximately 19 million books and electronic resources. It also houses the personal 3,800 volume library of John Adams. You know – that John Adams – founding father and second president of the United States.
However, it’s not just the size that’s impressive but the Renaissance Revival architecture is quite beautiful as well. Designed by Charles McKim – a famous 19th century architect – the building was completed in 1895. The original building is a research library and an extension built later on in the 70’s serves as the general library.
A true “palace for the people” as it was described when it opened – besides books and literature, the library hosts special exhibitions, popular lectures and even concerts. Stop by Monday-Thursday 8am-8pm and 8am-5pm on Friday and Saturday. They are even open 11am-5pm on Sundays.
- Boston Public Library
- 700 Boylston Street, Boston, MA 02116
Smell the Flowers at the Boston Public Garden
The Boston Public Garden is a must-visit for anyone visiting the city. It is the first public garden in the country, and one of Boston’s beloved green spaces.
Located in downtown Boston, adjacent to the Boston Common, the garden is home to many mature trees, lots of formal flower beds, and a pond with water birds such as ducks and geese.
Some of the top things to do in Boston Public Garden include admiring the equestrian statue of George Washington, going for a swan boat ride, and snapping a photo of the famous “Make Way for Ducklings” statue. There’s also an unusual monument called the Ether Monument that commemorates the first use of ether as an anesthetic.
The park’s flowers are beautiful in spring, summer, and fall. Thousands of tulips in the spring create a breathtaking display. In the fall, changing leaf colors make for a pleasant stroll.
Allow two to three hours. Bring a picnic and take a break from sightseeing in the tranquil garden!
Recommended by Dhara from It’s Not About the Miles
- Boston Public Garden
- 4 Charles St, Boston, MA 02116
Stroll Through Beautiful Beacon Hill
Even if you’ve never been to Beacon Hill, you’ve for sure seen photos of this classic Boston neighborhood. Best know for it’s narrow streets, red brick homes and buildings, Beacon Hill is one of the must do things to do in Boston when you visit. This cozy part of the city is home to quite a few of Boston’s most popular landmarks and places to see.
One of the most famous streets in all of Beacon Hill is Acorn Street. With its narrow cobblestone pathway, lined with old historic brownstones, it gives the visitor a glimpse into old colonial Boston. If you happen to visit Boston in winter, this area is especially festive during the holidays when it’s decorated with Christmas lights and wreaths.
Be a Star For the Day on a Movie Tour
No article about wicked smart things to do in Boston would be complete without including a little bit of info about that iconic phrase that’s become synonymous with Boston.
As you may know already, those two words were made famous in the 1997 movie Good Will Hunting. The movie, set in Boston, is written by – and stars – Matt Damon and Ben Affleck. The storyline is based on Damon’s character – Will Hunting – a self-taught natural genius who worked at MIT (Massachusetts Institute of Technology) as a janitor.
Will anonymously solves a complicated math equation and a professor tries to help him realize his true potential. This movie had everyone rooting for Will and people everywhere outside of Boston saying “wicket smaht”. Which, by the way, in the movie was said by Ben Affleck’s brother in real life, Casey. He also went on to do one of the funniest Saturday Night Live skits of all times about Boston.
If you are a Good Will Hunting fan or just a movie fan in general, one of the best things to do in Boston is a movie tour that includes visiting over thirty locations from the dozens of movies that have been filmed in Boston.
Even More Things to do in Boston
Boston makes it super easy to get around and see even more things on your own. The Go City Boston pass is an economical way to sightsee your way around the city. You can choose from over 40 activities and venues to fit your schedule be it one, two, three, five, or seven consecutive days.
Alternatively, the Boston City Pass, includes entrance to the New England Aquarium and the Museum of Science plus a visit to two other venues from a list of available options. The pass is valid for nine days from the first date of use and is perfect for someone visiting on a weekend or long weekend.
Where to Stay in Boston
For a historic downtown hotel – The Fairmont Copley Plaza has easy access to all the top sites. It opened in 1912, has hosted presidential dinners, and is home to Oak Long Bar, named Boston’s best hotel bar. For an extra special stay, book a room on the hotel’s Gold Floor, which includes private check-in, club lounge access, and complimentary breakfast, snacks, and evening hors d’oeuvres. Thanks WineTravelista.com for the suggestion.
Watch the sailboats glide across the water from the Boston Marriott Long Wharf. This harborside hotel is steps away from the New England Aquarium and you can be at Quincy Market and the North End in no time from this prime location. From this location you can even take a shuttle to the airport. It’s the perfect spot if you fly into the city and don’t have plans to rent a car.
In Cambridge, the Sheraton Commander Hotel is in the ideal location close to Harvard and its museums. The Harvard Museum of Natural History and the Peabody Museum of Archeology and Ethology are both within walking distance. The hotel has a restaurant and bar and is pet friendly.
When is the Best Time to Visit Boston
The best time to visit Boston is from June to October. The particularly good fall weather makes touring on foot a lot more enjoyable. Summer is crowded and hotels are a bit more expensive but the abundance of activities like patio dining, outdoor concerts and baseball games makes it worth it.
Plan a Visit to Boston
Boston is such an exciting, fun destination to visit in the United States and there’s way more things to do than what’s on this list. You could easily spend a week there and never run out of activities. So, the next time you are planning a vacation or a long weekend getaway, why not consider visiting Boston? You won’t be disappointed.
Need help planning a Boston trip? Here’s some of my favorite resources:
- For flight info and tickets prices use Skyscanner.com.
- To book a package with a flight and a car all at once use Expedia.com.
- My absolute favorite website for hotels, hostels and even some long term stays is Booking.com.
- To check out home stays and long term places try VRBO.com.
- For cars and vehicle rentals – Rentalcars.com.
- See real reviews and what other travelers are saying at Tripadvisor.com.
- For local tours & experiences use the helpful Viator.com
- And finally, one of the most important items in your travel plans is travel insurance. Browse a variety of coverage options at at TravelInsurance.com.