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 starts 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

If you’re planning to explore Boston without venturing too far beyond its city limits, renting a car isn’t necessary.

The challenge of finding and paying for parking can become an inconvenience in Boston.

Instead, staying at a hotel in the downtown area places you close to the top attractions.

This allows you to walk, use public transportation, or take an Uber to reach most destinations effortlessly.

However, if you intend to combine your Boston trip with nearby adventures, having a car becomes more practical.

Boston also serves as a fantastic starting point for a New England road trip, so it’s wise to book your rental car in advance through DiscoverCars.

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.

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

This 2.5-mile path, easily recognizable by its red brick markers, takes you through many of the city’s key areas.

Each of the 16 stops along the trail highlights pivotal moments from the American Revolution or other important chapters of the nation’s past.

These include landmarks like Faneuil Hall Marketplace, the Old State House, and a walk that leads into the historic North End.

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.com.

The Freedom Trail reveals the layers of America’s history and provides a fantastic way to explore the variety of Boston’s neighborhoods.

Insider tip: Use this convenient map to find your way along the Freedom Trail.

2. Visit The Boston Common

Boston Common The oldest public park in the United States, was established in 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 the 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 garden’s main attraction, the renowned Swan Boats, gently moves across the peaceful lagoon, offering an essential Boston experience.

With carefully arranged flower beds and well-known sculptures like the George Washington Statue, the Boston Public Garden is a beloved spot for nature enthusiasts 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. An Unforgettable Evening on a Boston Harbor Sunset Cruise

Setting off on a Boston Harbor sunset cruise offers breathtaking scenery, calm waters, and the mesmerizing glow of the setting sun.

As the boat glides across the harbor, you’ll enjoy sweeping views of Boston’s famous skyline, historic landmarks, and charming waterfront.

This top-rated Boston Harbor Sunset Cruise comes highly recommended.

5. Take a walk around the Back Bay

With its elegant streets adorned with Victorian brownstones, high-end boutiques, and modern restaurants, Back Bay radiates an enduring appeal.

Take a leisurely walk along notable avenues like Newbury Street, featuring upscale brands such as Chanel and luxury hotels like The Newbury Boston.

Then, explore Commonwealth Avenue, which bursts into color with blooming cherry blossoms each spring.

Admire architectural landmarks such as Trinity Church, the Boston Public Library, and the John Hancock Tower, all nestled in the iconic Copley Square.

6. Admire the Boston Public Library

The Boston Public Library stands as one of the city’s defining landmarks.

As the first publicly funded municipal library in the United States, it symbolizes both a repository of knowledge and a masterpiece of architecture.

Visitors are captivated by the striking exterior of the McKim Building, featuring an impressive marble staircase and intricate craftsmanship.

Within its walls, an expansive collection of books, manuscripts, and artwork offers a journey through time and genres.

Whether seeking a quiet corner for study, a glimpse into history, or one of Boston’s most photogenic spots, the Boston Public Library is an essential stop.

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 the 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’s North End Small-Group Walking Tour
• Boston Small-Group Food Tour with Tastings
• Boston Seafood Lovers Food & History Walking Tour
• Boston Tasty Donut Adventure & Walking Food Tour

8. Stroll Through Beacon Hill

Beacon Hill is a lovely, old neighborhood in Boston.

I honestly think it’s my favorite part of the city!

Walking through this historic neighborhood feels like stepping into another era. Federal-style, colonial, and Victorian homes, some dating back to the 1700s, line the narrow, lantern-lit streets.

Grab a coffee from a cozy Beacon Hill café and enjoy a leisurely morning or evening stroll through this charming area.

Don’t miss Acorn Street, a well-known spot still paved with cobblestones, offering an iconic scene that draws photographers from all over the country.

Afterward, head to Louisburg Square, where you can admire some of Beacon Hill’s most luxurious residences.

The area exudes refined elegance, giving you a glimpse into the lifestyle of Boston’s elite from years past.

With its rich history and undeniable charm, Beacon Hill is an absolute must-see when visiting Boston.

9. 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.

Today, the area buzzes with activity, featuring a wide range of shops, restaurants, and outdoor vendors. Part of this historic complex, Quincy Market, is a bustling food hall offering a diverse selection of dishes.

From classic New England clam chowder and lobster rolls to sushi and tacos from around the globe, there’s something to satisfy every craving.

Adding to its lively environment, the marketplace frequently hosts live performances, street musicians, and cultural events, making it a must-visit for anyone exploring the city.

10. Try Boston’s Signature Dishes

No visit to Boston is complete without sampling some of its iconic dishes! Here are a few must-visit spots:

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

Union Oyster House

Known as the oldest restaurant in America, Union Oyster House is a prime destination for oyster fans. Their clam chowder is equally famous, offering a delicious taste of Boston’s culinary heritage. The historical atmosphere only enhances the dining experience, making it truly memorable.

Neptune Oyster

For one of the city’s top-rated lobster rolls, Neptune Oyster in the North End is a must. This bustling eatery is known for its fresh seafood, and while there’s often a wait, it’s well worth the time.

The Boston Sail Loft

Famous for its clam chowder and waterfront views, The Boston Sail Loft provides a cozy, laid-back dining experience. Locals have loved their clam chowder for years, making it a Boston classic.

Mike’s Pastry

A visit to Boston wouldn’t feel right without trying a cannoli from Mike’s Pastry. This beloved bakery draws crowds with its wide array of cannoli flavors, offering a sweet ending to any meal.

Omni Parker House

Home of the original Boston Cream Pie, the Omni Parker House is a must for dessert lovers. Enjoy a slice of this iconic treat at the very place where it was first created.

Each of these establishments captures the essence of Boston’s rich food culture, offering more than just a meal – it’s a taste of the city’s history and passion for quality.

Make sure to check their websites for the latest menus and reservation details.

11. The Isabella Stewart Gardner Museum: A Masterpiece of Art and Architecture

Founded in the early 1900s by the visionary Isabella Stewart Gardner, this museum is a testament to its founder’s passion for art, culture, and adventure.

Isabella, a forward-thinking woman with a love for travel and bohemian living, personally oversaw the creation of the museum’s stunning Venetian-style palazzo. Within its walls, visitors are treated to various paintings, sculptures, tapestries, and decorative arts, all beautifully framed by remarkable architecture.

Interestingly, in 1990, 13 pieces of art were stolen from the museum, an unsolved case to this day. Valued at $500 million, this heist remains one of the largest in history. The incident is featured in the Netflix documentary This Is a Robbery: The World’s Biggest Art Heist.

There’s even a $10 million reward for information leading to the recovery of the missing pieces, making this museum not only a must-see for art lovers but also a place shrouded in mystery and intrigue.

12. Wander Around Harvard Square

You’ll find the prestigious Harvard University across the Charles River in Cambridge.

With its rich historical background, striking architecture, and intriguing museums, the campus offers plenty to discover.

At the heart of the campus is Harvard Square, bustling with cafes, bars, and the well-known Harvard Coop, a sprawling bookstore.

A standout feature on the grounds is Annenberg Hall, whose remarkable design brings to mind the grandeur of Hogwarts’ Great Hall.

Be sure to follow tradition by rubbing the foot of the John Harvard Statue for a bit of luck.

For a deeper dive into its history, a guided tour of Harvard University will allow you to walk in the footsteps of world leaders and notable alumni.

13. Experience Boston in an Unconventional Way with a Duck Boat Tour

For an adventurous twist on sightseeing, hop on a duck boat tour through Boston.

These amphibious vehicles, originally built for use in WWII, have since been transformed into a fun and unique way to explore the city.

During the tour, you’ll traverse both the streets and waterways, allowing you to experience famous landmarks like Faneuil Hall, the Old State House, and the USS Constitution from two different perspectives.

Led by lively and informative guides, these tours offer an engaging mix of Boston’s history and present-day stories, making them an unforgettable outing for visitors of all ages.

14. A Visit to Fenway Park: A Must-Do in Boston

Whether you’re a baseball enthusiast or simply looking for a way to entertain your significant other (I fall into the latter category, lol), a trip to Fenway Park, the oldest baseball stadium in the country, is a must when in Boston.

If you’re in town during baseball season, attending a Red Sox game is an unforgettable experience, filled with excitement and the roar of passionate fans.

Even if the season has ended, a guided tour of Fenway Park is well worth it. Walking around this iconic stadium feels like stepping into a living piece of American history.

Every corner of Fenway has a story to tell, from legendary games to celebrated players. The tour even gives you the chance to sit in the oldest seats in Major League Baseball, connecting you directly with the ballpark’s rich past.

After the tour, grab a drink at Bleacher Bar, a pub tucked under the bleachers in centerfield, offering a view like no other!

15. North End: Boston’s Charming Italian Quarter

Boston’s North End, often referred to as the city’s Little Italy, is a bustling neighborhood brimming with incredible Italian eateries, cozy coffee shops, and classic delis.

As Boston’s oldest neighborhood, it also hosts key stops on the Freedom Trail, including the historic Paul Revere House.

While exploring North End, don’t miss out on the ongoing debate over the city’s best cannoli – be sure to sample both Mike’s Pastry and Modern Pastry to decide for yourself!

16. Day-Trip to Martha’s Vineyard

A trip to the iconic Martha’s Vineyard is a perfect way to leave behind the busy city and soak in New England’s charm and natural splendor.

This peaceful island offers a relaxing retreat with its pristine beaches, historic lighthouses, and quaint coastal villages.

Spend your day exploring the island’s scenic routes, whether cycling along coastal paths, wandering through towns like Edgartown and Oak Bluffs, or unwinding on one of the island’s soft sandy beaches.

Martha’s Vineyard also offers a rich arts and culture scene, with art galleries and boutiques inviting you to browse.

Whether you’re seeking outdoor exploration, relaxation, or simply a slower pace, a day trip to Martha’s Vineyard provides a refreshing break from Boston’s hustle.

For an all-inclusive experience, I recommend this popular Martha’s Vineyard Day Trip from Boston with a Round-Trip Ferry & Island Tour Option.

Related: Which Boston Harbor Island is the Best to Visit?

17. Dine at Skywalk Observatory

The Skywalk Observatory is a must-visit in Boston, offering stunning, sweeping views of the city’s skyline and its notable landmarks.

Perched high atop the Prudential Tower in the Back Bay neighborhood, this observation deck provides unmatched 360-degree perspectives of Boston and the surrounding areas.

From the vibrant streets below to the reflective waters of the Charles River, the view from the Skywalk offers a captivating look at the city’s diverse architecture and scenic landscapes.

18. USS Constitution Museum: A Trip from the Past

For history enthusiasts, a visit to the USS Constitution is a must. As the oldest commissioned warship still afloat, it offers a fascinating glimpse into early American naval history at the Charlestown Navy Yard.

At the USS Constitution Museum, you’ll uncover the ship’s pivotal role in the War of 1812, where it earned a lasting reputation as a symbol of American resilience and ingenuity.

With interactive exhibits designed to engage visitors of all ages, the museum provides an immersive experience that brings the life of sailors over 200 years ago to vivid detail.

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.

A trip to the brewery offers a fantastic chance to gain firsthand knowledge about the brewing process.

Through guided tours, you’ll delve into the rich heritage and creative spirit behind Samuel Adams, with the added treat of sampling a selection of their acclaimed brews along the way.

20. Explore Salem, Massachusetts

Located just a short drive from Boston, Salem is best known for the infamous witch trials of 1692.

Visitors can explore notable sites like the Salem Witch Museum, which sheds light on the dramatic events of the trials and their lasting impact.

Salem’s downtown offers a mix of quirky shops, art galleries, and inviting restaurants, making it a delightful place to wander.

Whether you’re drawn by the town’s rich history, curious about the supernatural, or simply looking to enjoy a scenic New England destination, Salem is a top spot to visit while in Boston.

21. The Institute of Contemporary Art: A Cultural Gem in Boston’s Seaport

Boston’s Institute of Contemporary Art (ICA) is a vibrant hub for art lovers, drawing together fascinating works from across the globe.

The museum itself is an architectural marvel, with striking design and stunning views of the waterfront.

Visitors can enjoy a diverse lineup of exhibitions, performances, film screenings, and even hands-on classes, offering something for every creative interest.

Whether you’re looking to dive into modern art or explore pieces by renowned contemporary artists, the ICA delivers an engaging experience.

With a focus on promoting fresh perspectives, diversity, and open dialogue, the ICA stands out as a key player in Boston’s cultural landscape. Don’t forget to visit the deck for spectacular views of Boston Harbor!