9 Tours to Exploring Boston Like a Local

Coming soon to Boston and want to get up close with the patriotic city? Instead of planning travel routes on your own, let professional guides show you the must-see highlights of New England's capital.

These are 9 tours in Boston that will provide you with a fun and efficient way to experience everything the city has to offer ????

Entrance to Quincy Market at Faneuil Hall, downtown Boston

Tour 1: The Freedom Trail – Guided tour of the sites of the independence declaration

The Freedom Trail tour is the central foundation for a trip to Boston. The city's role in the U.S. independence at the end of the 18th century granted it the status of the patriotic city (although the declaration itself was held in Philadelphia). Boston is the heart of the great rebellion against the British with the legendary Tea Party and the battles of the War of Independence that took place in and around it.

The Freedom Trail tour is the foundation for a trip to Boston and includes 16 sites along a four-kilometer route all related to U.S. independence.
The tour starts from downtown Boston heading north through the North End and crosses the Charles River to Bunker Hill in the Charlestown district.
The tour starts at Boston Common Park and includes the Massachusetts State House, Granary Burial Ground, Old South Meeting House, the Old State House surrounded by skyscrapers, Faneuil Hall Marketplace, Paul Revere House (“The British are coming…”) in the North End, Old North Church, the Bunker Hill Monument, and ends at the USS Constitution in Charlestown Harbor.

There is a wide variety of Freedom Trail tours. As these are the city's most popular tours, they feature a big and fun show, including guides dressed as American Revolution heroes and other actors in late 18th-century clothing.

Click here for the full Freedom Trail tour from Boston Center to Charlestown…

Tour 2: Guided Walking Tour of Boston's Major Sites

The Freedom Trail tour focuses on the sites of the American Revolution and features actors and production. The other Boston sightseeing tours aren't as loud as the Freedom Trail tour and allow you to get to know downtown intimately with a guide who isn't dressed like George Washington.

There are quite a few tours focusing mainly on Downtown Boston, Beacon Hill district, North End, and Back Bay. These tours also incorporate the main sites of the American Revolution but present them in a different way. The walking tours are usually less crowded, conducted in small groups, and focused on a central theme.

Click here for a variety of thematic tours in the heart of Boston…

Tour 3: Guided Tour of Fenway Park, home of the Boston Red Sox ⚾️

The Boston Red Sox are an iconic Boston institution, even more so than the prestigious universities on the northern bank of the Charles River across. Boston's legendary baseball team was one of the eight founding teams of the MLB League and the first winner in the history of the World Series. The team was famously known for the “Curse of the Bambino,” a nickname for Babe Ruth. After the legendary player was sold to their arch-rivals, the New York Yankees, the Red Sox failed to win a championship for 86 years.

The tour of Fenway Park in the Fenway-Kenmore area is considered one of the most popular in the city. It takes place inside the legendary stadium and includes fascinating displays on the team's history and its legendary stars, including the Bambino.

Click here for a guided tour of Fenway Park, home of the Red Sox…

Tour 4: Cambridge – A Guided Tour of Harvard University Campus and MIT

Boston is the academic city of the USA, with dozens of campuses of academic institutions spread across the large metropolis. The most important institution in the metropolis is Harvard, the historical private university considered the oldest and most prestigious in the United States (competing with Yale in New Haven, which was established as a sort of branch of Harvard).

Click here for a guided walking tour of Harvard University's campus…

The tour of the university campus includes:

The center of the campus, Harvard Square and Harvard Yard
A tour of faculty buildings and the library named after Harry Elkins Widener
Entry to some of the university museums, such as the Harvard Art Museums, the Peabody Museum of Archaeology and Ethnology, and the Harvard Museum of Natural History

There are tours that also include the Massachusetts Institute of Technology campus, or MIT, located a bit to the east. There are also separate tours of MIT that are perfect for science and technology enthusiasts at this world-leading institute.

Click here for a guided walking tour of the MIT campus…

Tour 5: Lobsters and Seafood – Culinary Tours in the Heart of the City

Boston is a unique culinary city in the USA and owes its thanks mainly to the abundant sea life of Massachusetts Bay, stretching from Cape Cod northwards to Nova Scotia in Canada. Beyond whales (a popular tour in itself), lobsters thrive in these waters, perhaps the delicacy most associated with all of New England.

Click here for a tasting tour of Boston's finest seafood…

Boston, like other cities in Maine, Rhode Island, and Connecticut, enjoys a fresh supply of lobsters and other plump seafood. Some seafood, crabs, and lobsters are caught from the wild, but most often they come from aquaculture, allowing for efficient and readily available marketing.

The city offers a plethora of seafood, crabs, and lobsters in a variety of preparations
The culinary tours focusing on seafood are some of the most popular in the city, featuring tastings of different types of crabs, shrimps, and lobsters in a variety of places including markets, street stalls, and even specialty restaurants
The tours concentrate in the heart of Boston, mainly around Faneuil Hall, the city's famous food market, and the waterfront

If seafood makes your stomach turn a bit, the city has a leading Italian food scene, especially in the North End district, and there are quite a few tasting tours there as well. There are also beer and bar food tasting tours, donut tours, etc. You definitely can't leave Boston hungry. ????

Click here for the North End pizza and Italian food tasting tour…

Tour 6: Whale Watching Cruise from Boston Harbor

Whale watching is one of the most renowned activities in New England and is very popular among those visiting the Northeast during the summer. There are many tours that depart from all New England ports, and of course, from the largest port in the area, Boston Harbor. It's an especially exciting experience that's very popular among tourists visiting Boston. It includes a certified guide who explains everything about the giant marine mammal, and of course, watching their movement in the bay waters in front of the city or towards Cape Cod Bay.

Click here to sail in search of the whales in Massachusetts Bay…

Tour 7: A Guided Tour Following the Witches of Salem

Besides academia, lobsters, and a multitude of Oscar-winning films, Boston is also famous for its witches and the Halloween vibe across the USA. Salem is a suburb north of central Boston and is identified with the witch trials held there in the late 17th century. Today, the city is an integral part of popular culture, with its main industry being dark tourism (it's really not that scary!!) and attractions linked to the world of witches.

Click here for Salem's spooky night tour in the footsteps of ghosts…

The tours in Salem provide a close-up experience of America's most fun culture, Halloween pumpkins, the understood fear of the holiday, and the atmosphere that most embodies autumn in New England (with the colorful foliage in the background, of course).
The city tours include the somewhat grotesque (and super popular) Witch Museum, a central walking tour with landmarks related to the trials, and a visit to the historic Salem maritime site with the long Derby Wharf.

Click here for a guided walking tour in Salem's center following the witches…

Tour 8: Day trip guided tour from Boston to Plymouth, the Mayflower city

American history is fully associated with the city of Boston, but British history in America is more associated with the city of Plymouth, a little to the south. Plymouth is the famous landing city of the Mayflower ship, the Puritan settlers who left from Plymouth, England (originally departing from Leiden in Holland but needed to dock in England) and landed at Plymouth only in 1620.

Plymouth was the first European settlement in New England (the second after Jamestown in Virginia, and in general, the Spanish had already settled in Florida decades earlier). It is still considered an American icon today, mainly because it was a group persecuted for their religion and is part of the American refuge ethos (unlike Jamestown, which was a crown colony).
The guided tour in Plymouth follows the Mayflower and Plymouth Rock. It includes a tour of the historic homes of the Puritan settlers, the Pilgrim Hall Museum, and also focuses on the figure of Chief Massasoit, who helped the settlers acclimate.
The tour often includes the Plimoth Patuxet Museums, a historical reconstruction of the first settlement.

Click here for a guided day trip to Plymouth, including a visit to Plimoth Patuxet…

Tour 9: Guided Day Trip from Boston to Cape Cod or Martha's Vineyard

Massachusetts is a stunning summer (and fall with its foliage) tourist destination. Besides the history of Plymouth and the witchcraft world of Salem, it's worth taking a day trip from Boston to the magnificent Cape Cod, just a short drive south of the city. There are plenty of guided day trips leaving early in the morning from Boston toward the town of Provincetown at the northern tip of the legendary peninsula.

Click here for a day trip from Boston to Plymouth and Cape Cod…

Along the drive, there are stops in towns and attractions of Cape Cod including Sandwich, Hyannis known for its Kennedy family connections, Brewster home to the famous Cape Cod Museum of Natural History, and of course the Pilgrim Monument and Provincetown Museum.

There are day tours that include a cruise to the luxurious and beautiful vacation island Martha's Vineyard (cruise from Hyannis or Plymouth). There are separate day trips to Martha's Vineyard that include a cruise from Boston. These tours often also include a hop to the neighboring island Nantucket and whale watching.

Click here for a day trip cruise from Boston to Martha's Vineyard…

7 Tips from Guy for Awesome Tours in Boston!

Boston is one of the most historic and unique cities in the United States. The capital of New England is a city rich in culture, boasting some of the leading museums in the Western Hemisphere. It’s also the most important city in the U.S. academically, home to numerous institutions headed by Harvard and MIT. There's plenty to see and do in Boston, from sights and shopping streets to delightful parks, promenades, waterway cruises, and more. Boston is also a culinary haven, offering tastes of local lobster to fine Italian cuisine brought over by Italian immigrants who settled in the city in the late 19th century.

The Custom House Tower in downtown Boston

How to choose the right tour for you? – It's super important to be sure about the tour you choose and only go if it truly excites you. Some tours might not be for everyone, like Boston's tasting tours that naturally focus on everything non-kosher—from lobsters to seafood and even pork ribs for dessert. If lobsters are a bit much, there are less intense culinary tours available, like pizza or donut tours.
Group size vs. price – There's a key rule when booking tours—the larger the group, the more wallet-friendly the tour. However, with smaller, more intimate groups, you can tailor the itinerary to your personal interests, but be prepared for a higher price.
The Capital of New England – Boston's stature goes far beyond that of a major metropolis. The city is the capital of Massachusetts and also the former official territory capital of New England under British rule. Tours and excursions include not only Boston but also historic cities nearby like Plymouth, Salem, and of course the university town of Cambridge.
Comfortable Shoes – We know appearance matters, but do your feet a favor and bring closed, comfortable shoes for the tour. Walking around Boston is no small feat, and you don’t want to wake up with sore feet and miss another day of exploring the streets.
Dress appropriately – Tours in Boston run throughout the year, both indoors and outdoors. On hot summer days, it's a good idea to wear light clothing. In winter, it can be freezing, so come prepared with warm clothing that can be easily removed when entering indoor places.
Backpack with drinks and light snacks – Guided tours are a form of group activity designed for participants' convenience, but they also follow a fixed schedule. Tours involve walking and, more challenging, require listening and concentration. To avoid holding up the group or getting hungry, it's smart to bring a backpack with water, drinks, and some kind of snack in case you get peckish.
Read Up Before You Go – There's nothing more appetite-whetting than snacking on a bit of information about your tour destination the night before. For those who love to travel and deeply explore places, some basic prep will give you a bit of orientation. Once you arrive at your travel destination, you'll already get what the guides are talking about and have a clear context.