10 Best Boston City Tours

Discover the history of the city in a fun way - there are guided tours for every taste!

Matteo Gramegna

Matteo Gramegna

8 min read

10 Best Boston City Tours

Boston | ©Jayden Burdick

Looking for what to see and do in Boston? You can tour on your own with the risk of missing a landmark or choose a guided tour and get the most out of your holiday.

One of the advantages of taking a guided tour of Boston is that you'll be able to choose from a range of different themes, from those focused on the city's rich history to foodie tours.

1. Taste North End pizza and learn about the history of the neighbourhood

North End Pizza| ©David McKelvey
North End Pizza| ©David McKelvey

Like New York, Boston was also the destination of thousands of Italian immigrants. The transalpine community settled in the North End, an area close to the harbour and downtown markets. In the 1930s, almost all the inhabitants were Italian and their restaurants attracted hundreds of customers every day.

The neighbourhood's establishments have survived the years and continue to turn out some of the best pizza in town.

It's worth booking a food tour of Boston to sample three pizzas at each of these historic restaurants.

The centrepiece is Hanover Street and halfway down, tucked away on a side street, is the home of patriot Paul Revere, a must-see stop on every tour. The guide will take you to other attractions in the neighbourhood - North Square Park, Old North Church, Bunker Hill Monument, etc. - explaining the history and curious happenings in this part of Boston.

  • Duration: about 2.5 hours
  • Price: between 40 € and 50 €.

Book a Boston Pizzeria Tour

2. Relive Boston's revolutionary history

Freedom Trail Emblem| ©Andrew Malone
Freedom Trail Emblem| ©Andrew Malone

The metropolis of Massachusetts played a key role in the history of the United States. The Siege of Boston blockaded the city from April 1775 to March 1776 and triggered the American War of Independence.

Tours follow the famous Freedom Trail, a red brick path through historic neighbourhoods. Guides liven up the tour with interesting facts and amusing anecdotes. On many of these tours, a stop is made halfway through the tour for a snack (included in the total cost).

  • Duration: between 3 and 4 hours
  • Price: between 60 € and 80 €.

Book your Boston history tour

3. Enter Fenway Park, the Cathedral of Baseball

At Fenway Park| ©Joe Passe
At Fenway Park| ©Joe Passe

In the United States, baseball is a true ritual. The professional league was born in the 19th century and one of the most historic franchises is the Boston Red Sox. Since April 1912, the legendary American club has made Fenway Park its home.

It is the oldest stadium in the Major League; it has been the scene of the team's successes and has hosted a multitude of concerts and political rallies.

Guided tours will take you to discover the records and secrets of "America's most beloved ballpark". Among other things, you'll see the famous Pesky's Pole, the pole on the right field foul line dedicated to shortstop and third baseman Johnny Pesky. He was a legendary player and the first batter to score 6 points in a 9-round game.

The stadium is located in the city centre, in an area known for its restaurants and nightclubs. If you didn't get your Red Sox ticket, you can turn to a neighbourhood classic: Cask 'n Flagon, a pub that's been guarding the same corner since 1969 (62 Brookline Avenue).

  • Duration: 1 hour to 1.5 hours
  • Price: around €30

Book your visit to Fenway Park in Boston

4. Guided tour of MIT

Outside MIT| ©Fcb981
Outside MIT| ©Fcb981

The Massachusetts Institute of Technology is one of the most famous universities not only in Boston but in the whole of the United States.

If you like mathematics, science and technology in general, this is a must-see. Astronaut Buzz Aldrin, Salman Khan (the founder of the Khan Academy) and Andrea Wong (the president of Sony), among others, studied here.

The guides are the students themselves, who will give you an insight into the history of the university. Among the buildings you'll see, it's worth mentioning the Green Building (a slender building designed by architects I. M. Pei and Araldo Cossutta) and the Stata Center, a complex designed by the famous Frank Gehry.

  • Duration: just over 1 hour
  • Price: between 10 € and 20 €.

5. Cruise down the Charles River in an amphibious vehicle

Boston amphibious vehicle| ©dorinser
Boston amphibious vehicle| ©dorinser

A great experience if you visit Boston with children. It's not every day you get the chance to ride in an amphibious vehicle inspired by a famous World War II model. This "bus with a shell" leaves the streets to get wet in the river. A spectacular entrance that will amaze your little ones.

The route is quite extensive as it runs both on asphalt and in the water. The list below shows some of the landmarks that you can admire from your seat:

  • Boston Public Library, the first in the United States. Its neo-Renaissance silhouette was designed by architect Charles Follen McKim.
  • Boston's Tea Party Museum, the interactive floating museum that delves into the history of the Tea Party Riot, the episode that sparked American independence.
  • Esplanade, a large riverside park. It is beautiful in all seasons, especially when autumn turns the leaves red.
  • Longfellow Bridge, a stone and steel bridge connecting Boston to Cambridge. It was built thanks to the City Beautiful Movement, an urban planning movement led by architects and landscape architects that reached its peak in the early 20th century.
  • Boston Aquarium, best known for the Giant Ocean Tank, a huge tank where sharks swim.

The river cruise lasts about 20 minutes, which is more than enough time to take some pictures of the skyline. An audio guide in several languages, including Spanish, is available throughout the tour. It can be a very interesting option if you are only in Boston for one day.

  • Duration: about 1 hour and a half
  • Price: between 50 € and 60 €.

6. Travel through the city by tram

Boston Trams| ©photohp
Boston Trams| ©photohp

An alternative to Boston's tour buses. In this case, instead of a double-decker bus, these routes take place aboard an Old Town Trolley, a vehicle halfway between a bus and a tram.

The best thing about these tours is that they're easy! You can hop on and off wherever you want and as many times as you like.

You'll hear explanations from an expert guide at all times and, in many cases, you can enjoy an exclusive discount for Boston's Tea Party Museum. The Old Town Trolley operates at all times of the year and will stay in the garage only if the weather is very inclement.

  • Duration: between 2 hours and 3 hours
  • Price: around €40

Book your tour bus in Boston

7. Tour Boston by bike

Boston Bike Tour| ©Urban AdvenTours
Boston Bike Tour| ©Urban AdvenTours

Boston lies at the confluence of the Charles and Mystic Rivers and is spread over a series of peninsulas. The terrain is mostly flat, a factor that favours travel on two wheels. Guided tours will take you to discover the city's main neighbourhoods and most famous landmarks:

  • North End, Boston's Little Italy. Here you'll find pizzerias and restaurants specialising in the recipes of the transalpine country.
  • Bunker Hill Bridge, an iconic cable-stayed bridge spanning the Charles River.
  • John Hancock Tower, the city's most iconic skyscraper
  • Beacon Hill, an elegant hilltop district. Boston' s best ghost tours pass through here.
  • Trinity Church, the building that put the "Richardsonian Romanesque" architectural style on the map.
  • Back Bay, the neighbourhood with the largest number of skyscrapers and luxury shops.

Each tour will provide you not only with a traditional bicycle or ebike but also with a helmet and an expert guide. The tours are conducted in all weather conditions. The tour is cancelled only in case of snow, a very common phenomenon if you visit Boston in winter.

  • Duration: 2 to 3 hours
  • Price: between 60 € and 70 €.

Book a guided bike tour of Boston

8. Taste the seafood of the Atlantic

Clam chowder| ©Guitles Getaways
Clam chowder| ©Guitles Getaways

Boston is a major fishing port and an ideal destination for foodies. You'll find a host of restaurants serving oysters, clams, lobsters and other delicacies. Before you sit down at your table, your guide will tell you about the local history.

Typically, tours include four meals: clam chowder, lobster roll, oyster tasting and dessert. For even fresher fish, you can travel to the nearby islands. To that end, I recommend reading the post on how to get to Cape Cod from Boston.

  • Duration: about 3 hours
  • Price: between 100 € and 150 €. Please note that you will have to pay for alcoholic beverages separately.

Book your trip to Martha's Vineyard Island from Boston

9. Take a photowalk

Photowalk| ©Faith Crabtree
Photowalk| ©Faith Crabtree

Want to take the perfect picture? In Boston there are guided tours that take you to Beacon Hill, the most Instagrammable neighbourhood in the city.

It has a unique charm: its cobblestone streets are embellished by elegant mansions from the federal period. Your guide will take you around the most charming corners and explain the history behind each building.

  • Duration: between 1 and 2 hours
  • Price: about €40

Book your Photowalks around Beacon Hill

10. Discover Boston's beer culture

Boston Brewery| ©AntyDiluvian
Boston Brewery| ©AntyDiluvian

The Massachusetts metropolis holds several records: it is the best destination for recent college graduates, the best city for walking and also the city with the highest per capita alcohol consumption. There are thousands of bars and breweries scattered throughout Boston.

A guided tour is the ideal way to discover this side of the city. You'll travel aboard a bus and have the opportunity to sample a few pints. For more information, I recommend you read the post about the best food tours in Boston.

  • Duration: about 5 hours
  • Price: just over €100

Book a Boston Brewery Tour

Are there any worthwhile day trips?

Balllena in Boston| ©Alonso Javier Torres
Balllena in Boston| ©Alonso Javier Torres

Of course it is! The article on the 10 best excursions from Boston will give you plenty of ideas. There are mountains, pristine coastlines, cities, islands and other attractions.

If you're staying 3 days in Boston, I recommend setting aside a few hours to explore the surrounding area.