21 Best Things to Do in Boston [Bucket List]

The Best Boston Activities & Attractions Today!

A city that is historical, modern and bustling with stories at every corner. History buffs, foodies, art gurus; there is something for everyone to explore when in Boston.

Last weekend I was in Boston for a little getaway and fell instantly in LOVE with it!

Who else goes to a new place and instantly started imagining how they would live there?

Today, I am sharing the ins and outs of Boston, including all the must-do things to do in Boston.

Let’s dive in.

How to Navigate Boston

You don’t actually need a car if you’re just going to be within the city itself rather than out in the peripheries.

Bostonians know that searching for and shelling out cash on a parking spot can be rough.

Go downtown,​ and stay at a hotel near all the main attractions.

This ensures that you can walk to a bus or metro station, take an Uber conveniently to reach anywhere.

But a car is paramount if your Boston trip also involves other pursuits in the area.

Boston, MA – Launch City of Choice for New England Road Trip!

Remember to rent a car on RentalCars here BEFORE the trip.

Top Things to Do in Boston

1. Explore the Freedom Trail

So when you visit Boston, my number one suggestion for what to do is Walk The Freedom Trail.

If you love history – or just want to cover the main sights in town, Boston’s Freedom Trail is a must.

In this area, a two-mile scenic trail (indicated by red brick on the sidewalk) intersects many of the communities iconic regions.

Each of the 16 stops on the trail marks locations key to the American Revolution or other important events in U.S. history.

Specific ones are Everyday terms – Faneuil Hall-side connected with Downtown Crossing extending to the North End – and Rat Boats.

Guided tours give a more complete experience.

I would recommend this top rated Freedom Trail: Small Group Tour of Revolutionary Boston.

Check availability on Viator. Click here

In sum, The Freedom Trail sheds light on some of the most dramatic events in all American history and gives visitors a solid opportunity to get to know the wide variety of neighborhoods Boston has to offer.

Insider tip: A great map to help find your way along the Freedom Trail.

2. Visit The Boston Common

Boston Common The oldest public park in the United States, established 1634.

Boston Common takes you back in time and also provides you with a tranquil escape from the hustle-bustle of the city.

Stroll its picturesque walkways, relax on the green spaces and take in the sights of landmarks such as Soldiers’ & Sailors’ Monument and Parkman Bandstand.

The park is relaxed enough to picnic or even take a stroll.

Throughout the year, Boston Common also functions as a vibrant gathering place for community activities, festivities, and performances.

The bustling Frog Pond is suited for all ages, transforming from a splash pad in the summer to an idyllic ice skating rink come winter.

3. Relax in Boston Public Garden

Sitting next to the Boston Common is America’s first public botanical garden, the Boston Public Garden.

A sight of eternal significance, serenity and varied flora is what makes this spot a must-visit.

The iconic Swan Boats ply the still waters of the lagoon, providing a touch of Boston tradition; the park’s real star is its centerpiece garden.

The Boston Public Garden showcases immaculately groomed flower beds and striking monuments such as the George Washington Statue, providing a haven for nature lovers and photographers.

Insider tip: Visit during the fall to see beautiful autumn foliage in Boston’s iconic public spaces like Boston Common or the Boston Public Garden.

4. Go on a Boston Harbor Sunset Cruise

Hitting the waters on a Boston Harbor sunset cruise combines with stunning sights, placid seas and mystical mosaics of the setting sun.

As you cruise the harbor, take in spectacular views of Boston’s trademark skyline, nearby historic sites and green waterfront.

A good one is this top-rated Boston Harbor Sunset Cruise, which would be the perfect way to set the tone for your visit.

5. Take a walk around the Back Bay

Back Bay offers, to a good degree another shot at timelessness on its tree-lined streets of Victorian brownstones next to respectable boutiques and trendy restaurants.

Stroll down historic avenues such as Newbury Street where high-fashion boutiques like Chanel and chic hotels like The Newbury Boston reside.

Take a walk down Commonwealth Avenue, and stop when you get to the cherry blossoms.

Copley Square is home to architectural marvels like Trinity Church, the Boston Public Library and John Hancock Tower.

6. Admire the Boston Public Library

Photo by Brandee ModelA treasure of the city, the massive Boston Public Library is s symbol in its limestone grandeur.

Well, in addition to it being the first tax-payer funded city-based library of general appeal in America, it is known around the world as an icon of information and culture with distinctive architectural significance.

All are easily engrossed by the wonderful face of the McKim Building, with its grand marble staircase and intricate frosted detail.

The library is home to tens of thousands of books, manuscripts and artwork that span centuries and genres.

Whether you are in need of a peaceful study area; looking for some history, or simply one of the most Instagrammable spots in Boston, the BPL is not a place to miss.

7. Take a Food Tour

A food tour in Boston is an excellent way to get immersed in the city’s deep culinary culture.

Boston food is not served in one style, but it offers a journey of cuisine with its different neighborhoods and various restaurants.

A food tour is a great way to sample flavors without the headache of planning anything.

Each neighborhood – from the historic streets of the North End, to artisan treats in South End, and beyond – serves up flavors influenced by its unique culinary history.

Here are some of the top rated tours that I recommend

• Boston Small-Group Food Tour with Tastings
• Taste of Little Italy: Boston’s North End Small Group Walking Tour
• Boston Seafood Lovers Food & History Walking Tour
• Boston Tasty Donut Walking Food Tour

8. Stroll Through Beacon Hill

Beacon Hill is a lovely, old neighborhood in Boston.

I honestly think its my favourite part of the city!

When strolling though Beacon Hill, you almost feel like you are in a different era.

The streets themselves are narrow and lined with Federal-style, colonial & Victorian houses dating to the 1700s.

More importantly, stop by a local Beacon Hill coffee shop before you head out and go on an early morning or late evening holiday stroll through the neighborhood.

Be sure to stop by the famous Acorn Street, a picturesque cobblestone street that is one of only a few like it remaining in Boston.

This area is also commonly photographed, thanks to its charming historic appeal; Acorn Street is known for being among the most photogenic streets in America.

Next, head to Louisburg Square to see some of the mansions in all of Beacon Hill.

The air in this area is the sophisticated elegance of Boston high society long dead.

One place that you absolutely must visit in Boston is Beacon Hill, a formerly upscale residential area of the city that’s as gorgeous and full of history as it gets.

9. Try Boston’s Signature Dishes

If you tried some of these iconic Bostonian dishes, then don’t think it’s enough to say that you’ve been in Boston. These include:

• Clam chowder
• Lobster rolls
• Cannolis
• Baked beans
• Boston cream pie
• Oysters
• Fenway Frank

Union Oyster House

Union Oyster House (America’s oldest restaurant!) The clam chowder is Die Meisten’s signature dish as well. The history behind provides an extra to the experience of dining that one cannot forget.

Neptune Oyster

Neptune Oyster, North End —Said to have the number one lobster roll in town. A bit hole-in-the-wall and almost always a line, but it serves up fresh seafood that is fantastic.

Mike’s Pastry

A cannoli from Mike’s Pastry: No Boston trip is complete without one. This bakery is a local sensation and is best known for its extensive cannoli flavors. Prepare to be amazed.

The Boston Sail Loft

The Boston Sail Loft: This is a family style clam chowder place, with waterfront views and brick walls that delivers a relaxed ambience. The clam chowder has been a local staple for years.

Omni Parker House

No city is worth its sugary history if it doesn’t offer at least one storied dessert — in which case, every list of essential sweet stops in Boston has to start with the birthplace of the Boston Cream Pie: Omni Parker House. Taste a piece of the original at the restaurant where it was first sold.

In their legacy, ambiance and dedication to quality, all of these establishments are home to the flavors that have long breathed life into the eating culture of Boston. Make sure to visit their sites for menus of the day, and if there are any booking regulations have they lifted.

10. Faneuil Hall Marketplace

Faneuil Hall, built in 1742, is an active center located at the heart of downtown Boston.

Faneuil Hall is one of the most visited sites along the Freedom Trail,a gathering spot and market for locals and tourists.

Serving as an important platform during the American Revolution with historic speeches from figures such as Samuel Adams.

The marketplace is now filled with a variety of shops, restaurants and outdoor vendors today.

Within the complex is Quincy Market, a food hall with dozens of restaurants.

You be able to relish in everything from conventional New England clam chowder and spoil rolls towards infrequent gastronomy below the strip of sushi, tacos and more.

Live performances, street musicians and cultural events brings an intimate vibe to the marketplace.

11. Visit the Isabella Stewart Gardner Museum

Started by Isabella Stewart Gardner in the early 1900s, showcasing her large art collection.

An acclaimed wanderer, Isabella was a pioneering art collector who delighted in the experiences and artifacts of travel.

She carefully monitored the design and construction of the vast Venetian-style palazzo Interior collections with paintings, sculptures, tapestries and decorative art are on public display along with the architecture

One of the grandest spots in Boston to take photos, and a beyond extraordinary repository for Art & History – This is a museum

13 paintings were stolen from the museum in 1990, still one of Europe’s most discussed unsolved crimes.

The heist resulted in some $500 million in losses, making it one of the largest thefts in history. Now, the case is being covered in the Netflix documentary This Is a Robbery: The World’s Biggest Art Heist.

Oh and a lousy $10 million up for grabs if you can get the works back!

12. Wander Around Harvard Square

Just across the Charles River lies Harvard, one of the most esteemed universities in the world.

The campus is beautiful, steeped in history, home to a variety of wonderful architecture and strange museums.

Stroll around Harvard Square, heart of this Ivy League campus and home to cafes; bars; the huge bookstore Harvard Coop.

Annenberg Hall on the Harvard campus, a stunning architectural gem reminiscent of the Hogwarts Great Hall.

But you mustn’t skip the tradition of giving the foot on John Harvard Statue a nice pat for luck.

For a more enhanced knowledge, Harvard University walking tour will make you feel as of your world leaders and big-name alumni.

One highly-rated one at Harvard University Campus Guided Walking Tour.

13. Take a Duck Boat Tour

Best Way to Explore Boston = Duck Boat

Source (One of my favorite memories visiting Boston as a kid.)

Amphibious vehicles, first commissioned during WWII and now converted for sightseeing.

Now-a-days they make for a unique sight seeing excursion across land & water with an element of fun and education.

You can enjoy a duck boat tour from your seat for views of popular sights such as Faneuil Hall, the Old State House, and the USS Constitution that you recognize not just by land, but also by sea on Boston Harbor.

14. Catch a Game at Fenway Park

Whether you are into baseball or not (I am definitely part of the latter, lol), heading over to Wrigley Field is a must for any visit to Boston.

Go to a Red Sox game at Fenway if it’s baseball season, when the atmosphere in this stadium and those loud Boston fans is palpable.

If not, then possibly take a guided tour to learn more about the rich history of Fenway.

It’s a living piece of American history and walking around Fenway Park feels that way.

There’s a tale of an epic game or legend that has walked the field in every direction you look.

The tour allows you to feel the ballpark’s unusual ambiance and sit in Major League Baseball’s oldest chairs — giving you a physical connection to history.

HIGHLY-RATED TOUR OF HISTORIC FENWAY PARK Have a drink at Bleacher Bar, which is literally under the bleachers in centerfield.

The view is unmatched!

15. Stuff Yourself With North End

Boston’s Little Italy, North End is a thriving enclave of excellent Italian restaurants, and it also comes with coffeehouses to match as well tho traditional delis.

It is also Boston’s oldest neighborhood and home to a number of stops on the Freedom Trail, including the Paul Revere House.

Please weigh in with your opinion of the cannoli conundrum at Mike’s Pastry vs. Modern Pastry — this is North End classic feuding and we wanna hear what you think!

16. Day-Trip to Martha’s Vineyard

Few destinations are as emblematic of New England’s beauty and charm than Martha’s Vineyard, to which visitors escape the city for a refreshing visit.JScrollPane through>>>

It is a beautiful island that serves as both an idyllic getaway and, for many people who live in these lands, a summer escape to the great beaches keeps;

From biking along coastal paths, to strolling charming towns like Edgartown and Oak Bluffs or lazing on one of the island’s many sandy beaches, there are dozens of lovely ways to spend your days getting blissfully lost in outdoor activities.

Martha’s Vineyard also has a vibrant arts and culture, with art galleries to delight you as you browse your way through the shops.

A day trip to Martha’s Vineyard is the perfect escape from Boston, whether you seek outdoor adventure, relaxation or just want a change of scenery.

For a stress-free day trip, I would suggest this seamless Martha’s Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option.

17. Dine at Skywalk Observatory

The Skywalk Observatory is one of Boston’s standout attractions, providing incredible 360-degree views of the city and its treasures.

The observatory is located on the top of the Prudential Tower, at Back Bay and it offers 360-degree views around Boston and beyond.

The views from the Skywalk are always captivating, with more than fifty miles of colorful cityscape and varying architectural patterns painted across Boston’s canvas, whilst the busy streets below turn into ground water where all behavior echoes around like ripples through black static.

If you’re interested, I suggest booking your tickets ahead of time here: Boston Observation Deck Admission Tickets.

18. USS Constitution Museum: A Trip from the Past

For history buffs, the USS Constitution (the oldest vessel still in commission with the US Navy)/

Charlestown Navy YardStart here and discover early American naval history.

Visitors can explore the War of 1812 and its place in U.S. history through exhibits at the USS Constitution Museum, while experiencing how “Old Ironsides” helped to forge the American spirit as a symbol of resiliency & innovation.

Interactive exhibits make maritime history come alive for visitors of all ages.

19. Samuel Adams Brewery Tour

Well, he left an impression on America’s craft beer scene and Samuel Adams is a name synonymous with the industry that can’t be erased.

Visiting the BreweryThe brewery experience is one of hands on brewing.

The tours offer a real glimpse into the history of Samuel Adams as well as their innovative approach and tastings will leave you with quite a few to cheer for.

20. Explore Salem, Massachusetts

From Boston, its just a short trip to Salem and it should be at the top of your list for two reasons: one) Its historic past with those infamous witch trials in 1692.

At historic landmarks like the Salem Witch Museum, visitors can learn about this moment in history and its lasting legacy.

The historic center has a compact area of cool shops, art spaces and eateries, making for an easily walkable shopping district.

If you travel to Salem, whether for history buffs, interested in the occult or looking to wander through a quintessential New England town, any hop up from Boston is going to be an experience.

21. Institute of Contemporary Art Immersion

The Institute of Contemporary Art (ICA) is an expansion in Boston’s welcoming Seaport District and a dynamic focal point of inventive associations.

With stunning architecture and incredible views of the harbor, the ICA presents a beautiful environment for an exhibition complemented by its collection of work.

Its programming lineup includes exhibitions, performances, film screenings and courses to cater to a wide range of interests and passions.

If you’re into experimental art or want to see new pieces by famous contemporary artists, the ICA is a cool place.

The ICA sets itself apart from the rest of Boston culture by boldly embracing new ways, new times, and a variety of conversation. Plus, take time to enjoy beautiful views of Boston Harbor from the ICA’s deck.