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Visiting Boston for the First Time? Here's What to See and Do

From historical attractions to art, culture, and sports, first-time travelers have plenty to check out in this New England capital.

A sunny street in central Boston
Hi, I'm Katie!

Katie Nadworny is an Istanbul-based writer who specializes in travel and stories at the intersection of culture and politics in Turkey, Eastern Europe, and the Middle East. Her work has appeared in National Geographic, The Daily Beast, The Guardian, The Independent, and BBC Travel, among other places. She has lived in Turkey since 2013.

Boston is a city brimming with history, with winding back streets and brick buildings, a nod to the country’s colonial past. Its waterfront location is perfect for getting outdoors to enjoy lush green parks and breathe in the salty sea air. Besides being the center of culture and education in Massachusetts, this capital city is also known for its fierce local pride. First-time visitors, no matter their interests, are sure to find a wide range of activities in this New England destination. Here are some must-dos for your first trip to Boston.

1. Walk the Freedom Trail

Visitors walk around the Old State House in Boston.
Catch a glimpse of old and new along the Freedom Trail.Foto: f11photo / Shutterstock

Meander through Boston’s history.

This 2.5-mile (4-kilometer) walking path winds past many of Boston’s historical landmarks from the colonial and revolutionary eras. Marked with a red brick line, the path carries you through the heart of the city. Visit Faneuil Hall, explore the city’s Old State House, and see the site of the Boston Massacre before ending up in modern-day Boston at Copley Square. There are 16 set stops on the Freedom Trail, but the path allows for flexibility to explore the city at your own pace.

2. Immerse yourself in Boston’s museums

The interior of the Harvard Museum of Natural History in Boston.
The Harvard Museum of Natural History is a must when in Boston.Foto: EvgeniiAnd / Shutterstock

Art and culture thrive in this city.

Boston is full of museums, both large and small. Make sure to hit the major players, like the Museum of Fine Arts and the Isabella Stewart Gardner Museum, famous for its eclectic collection housed in an Italian-style villa. Afterward, dive into the region’s unique cultural history at spots like the Harvard Museum of Natural History. For a bargain on a day or two of museum trips, pick up a sightseeing pass, such as Boston CityPASS®.

3. Visit Fenway Park

Exterior of Fenway Park, America’s oldest ballpark.
Fenway Park is iconic among sports lovers.Foto: CiEll / Shutterstock

Watch a ballgame in America’s oldest ballpark.

Boston is a baseball town, and games are held at the iconic Fenway Park. Home of the Boston Red Sox, the park is an impressive site, even when it’s not baseball season. On a guided tour of Fenway, you can visit the roof deck that overlooks right field, see the famous 37-foot (11-meter) “Green Monster” as well as “Pesky’s Pole,” and learn why these highlights are significant to Red Sox history. If you have a chance, make sure to catch a home game to feel the energy of local Bostonians cheering on their team.

4. Discover the North End

Interior of a deli in Boston's North End.
You'll find authentic Italian food in the North End.Foto: Amanda Voisard / Viator

Explore Boston’s historically Italian neighborhood.

Boston is home to a large Irish and Italian population, and the Italian community once congregated around the North End neighborhood. With its dense brick buildings, twisting side streets, and many restaurants, Boston’s North End is a unique place to spend the afternoon. Visit the many churches in the area (including the Old North Church), stop by historical sites like the Paul Revere House, and taste the wide range of traditional Italian and American Italian food, including pizza.

Related: 9 Must-See Boston Neighborhoods and How to Visit

5. Take a Duck Tour

A Duck Tour vehicle travels on Charles River in Boston.
Boston's Duck Tours are a popular way to see more of the city.Foto: Alena Kuzub / Viator

See Boston from the water.

The renovated World War II-era amphibious vehicles known as ducks now serve as an excellent way to get out on the Charles River and experience Boston from the water. Pass the Boston Garden, the Boston Common, Beacon Hill, and Bunker Hill on land before driving off-road and into the river to get a water-side view of the city. For a comprehensive experience of the city, the Duck Boat Tours have it covered.

6. Spot whales

A whale tail emerges from the ocean in Boston.
This state is one of the top destinations for whale-watching.Foto: Amanda Voisard / Viator

See these gentle giants in their natural habitat.

Massachusetts is one of the top whale-watching spots in the world. Admire these majestic animals up close from Boston via boat. Cruise around the Stellwagen Bank National Marine Sanctuary at the mouth of Massachusetts Bay to spot whales and other marine life with the help of a naturalist guide. The area is a feeding ground for humpback, fin, minke, pilot whales, dolphins, sea birds, and more.

7. Go on a Boston pub crawl

People walk past a street lined with pubs in Boston.
Boston's pub scene is famous and well-worth exploring.Foto: Darryl Brooks / Shutterstock

Sample Boston’s local beers throughout the city.

The city that served as the setting for Cheers knows its beers. Bars and taverns dot the city, ideal places to experience Boston’s nightlife. Raise a few pints of local beer in the city’s historic drinking holes and hear stories about Boston's past. You can also swing by a brewery like Samuel Adams or Harpoon to learn about the Boston brewing process and taste these famed local beers.

8. Reenact the Boston Tea Party

A reenactment actress on a ship near the Boston Tea Party Museum.
This floating museum reenacts the events of the Boston Tea Party.Foto: Amanda Voisard / Viator

Relive a milestone in US history.

Play a part in one of Boston’s milestone moments at the Boston Tea Party Ships and Museum. This experiential floating museum lets you reenact the night of December 16, 1773 when patriots dumped imported tea from ships in protest against British taxes—an event that ultimately sparked the 1775 American Revolution. After joining costumed compatriots, dress up and board a replica ship to throw mock tea crates overboard before exploring the artifact-filled museum. Prebook tickets online or consider a self-guided audio tour that showcases the museum and tells the story of the protest.

9. Browse Beacon Hill

People strolling down a street in Beacon Hill.
Beacon Hill is one of Boston's most scenic neighborhoods.Foto: Alena Kuzub / Viator

Enjoy one of Boston’s prettiest enclaves.

Wedged between the Charles River and Massachusetts State House, Beacon Hill is one of Boston’s oldest and most picturesque neighborhoods. Stroll its steep cobbled streets past elegant Federal-period houses, dip into the restaurants, coffee houses, and boutiques of upscale Charles Street, and admire much-photographed Acorn Street, a picture-perfect sliver of colonial-era Boston. Unpack the area’s history and best photo ops on a Beacon Hill photo-walk or discover it alongside the Freedom Trail and other historical locales on a wider city bike tour or guided walk.

10. Experience Boston’s dark side

The graves at Granary Burying Ground.
Granary Burying Ground is home to the graves of notable Bostonians.Foto: Diego Grandi / Shuttertock

Uncover the city’s often haunting history.

Boston’s revolutionary past has left it with many poignant historical sites. Visit the Boston Massacre plaque commemorating the colonists shot by British soldiers here in 1770. The nearby Granary Burying Ground houses the graves of those killed and other notable Bostonians, as does the spooky, centuries-old Copp’s Hill Burying Ground. All three typically feature on Freedom Trail tours, while the graveyards are stock-in-trade for Boston’s ghost excursions. Alternatively, try a crime tour to trace some of the city’s most notorious murder and mobster cases.

This article features additional content written by Sarah Iredale.

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