17 INCREDIBLE Tours in Boston [January 2020]

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Boston is a historic American city that has a little bit of everything. It’s steeped in history, overflowing with culture, and tied together with stunning scenery. The modern charm of the city is just as enticing as its historic allure.

If you’re planning a trip to this exciting New England city, guided tours of Boston are a great option. They take the hassle out of planning and leave the itinerary and schedule to someone else. Plus, you’ll learn tons of insider information from your local guide.

Here are our picks for the best tours in Boston, Massachusetts!

Table of Contents

#1 – Boston Fenway Park: 1-Hour Guided Walking Tour

The perfect tour for sports fans

Boston Fenway Park: 1-Hour Guided Walking Tour

  • $
  • 1-hour
  • Fenway Park is the oldest ballpark in Major League Baseball
  • A great way to experience the local sports culture

Fenway Park is the iconic Major League Baseball stadium of the Boston Red Sox. Bostonians are passionate Red Sox fans, and this beloved ballpark and baseball team brings the city great pride and joy. This makes a stadium tour one of the best Boston tours.

Tours operate year-round and let you learn about the Red Sox on a more personal level. Visit the press box, see the Fenway Park Living Museum collection, and learn about this historic sports club’s impressive timeline. You’ll also go on top of the infamous “Green Monster”.


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#2 – Boston’s Freedom Trail Walk Into History® Tour

A great Boston tour for history buffs

Boston's Freedom Trail Walk Into History® Tour

  • $
  • 90-minutes
  • A very popular Boston tourist attraction
  • One of the best history tours you can take

On this historical tour of Boston, you’ll be guided along 11 of the 16 stops on Boston’s Freedom Trail. Visit some of the most significant landmarks of the United State’s revolutionary founding.

Your period-costumed Boston tour guide will lead the way and entertain you with facts and information on American history throughout the tour. See the beautiful Boston Common – America’s first public park. Visit the Granary Burying Ground – the final resting place of many brave American heroes.

Learn about American history from an up-close perspective. This Boston walking tour combines learning with entertainment and presents a great overview of the city.


Are you made of money? If not, our helpful Boston hotel guide was made for you!

#3 – Harvard: 70-Minute Hahvahd Tour

An insightful and educational tour

Harvard: 70-Minute Hahvahd Tour

  • $
  • 70-minutes
  • One of America’s oldest and greatest universities
  • Harvard is located 4 miles from Boston city center

Follow a current Harvard student through the world-famous Harvard University campus. You’ll get an insider’s perspective and learn all about the school’s current culture.

Meet your guide and group in the heart of Harvard Square before continuing on to explore the historic Harvard Yard. Learn tales of Harvard history and insight from a student. See major Harvard landmarks, like the Johnston Gate, the John Harvard Statue, Memorial Hall, and Widener Library. 


Haven’t found what you’re looking for? Try our hotel guide for Downtown Boston!

#4 – Old Town Trolley Tour of Boston

One of the best Boston sightseeing tours

Old Town Trolley Tour of Boston

  • $$
  • 1 day
  • 18 stops covered by the trolley route
  • A friendly conductor narrates the tour

Climb aboard the Boston trolley and enjoy convenient transportation and on-board entertainment. With your full-day trolley ticket, you’ll easily be able to tour all the highlights of Boston at your own pace.

There are 18 well-placed bus stops across the city that will connect you to over 100 Boston points of interest.

Hop on and off at any stop you’d like. This Boston tour by bus covers all the city’s main areas. These include Beacon Hill, Back Bay, the Theater District, and the Waterfront.


Planning a trip? See our list of the best things to see in Boston!

#5 – Boston Duck Tour: The Original and World-Famous

One of the most unique Boston city tours

Boston Duck Tour: The Original and World-Famous

Boston Duck Tour: The Original and World-Famous ( PhotoCredit – gettyimages.com )

  • $$
  • 80 minutes
  • See the city from land and from water
  • All tours feature a local guide

Discover Boston on a World War II-style boat that travels on land and water! Start your tour driving through Boston’s historic streets. Then, head right into the Charles River on one continuous journey.

You’ll travel past popular sites, including the State House, Bunker Hill, the Boston Common, and Copley Square. Enjoy unobscured views of Boston and Cambridge from the water.

You’ll learn lots of little known facts from your tour guide throughout your whole journey.


#6 – Boston’s North End: Secret Food Tour

A great tour for foodies

Boston's North End: Secret Food Tour

  • $$$$
  • 3 hours
  • Boston’s North End is nicknamed “Little Italy”
  • Enjoy a secret dish at the end of the tour

Explore Boston’s North End district on guided food walking tour. Enjoy the city’s famous Italian food, including specialties like fresh lobster rolls, Italian sandwiches, pizza, and cannolis.

This tour combines learning about Boston’s history with sampling the city’s cuisine. You’ll make seven stops to taste local dishes. All the while, your tour guide will entertain you with almost 400 years of American history.


Have some time in Boston? These are our favorite day trips from Boston!

#7 – Boston Tea Party: Ships & Museum Interactive Tour

A fun museum experience

Boston Tea Party: Ships & Museum Interactive Tour

  • $$
  • 1 hour
  • Interactive, guided museum tour
  • A great experience all ages will enjoy

Take a historical journey back in time and revisit a famous event that changed American history. The Boston Tea Party Ships and Museum is an interactive museum that lays out the events surrounding the Boston Tea Party and the American Revolution. 

Follow your costumed guide through all the areas of the museum. See restored Boston tea ships, throw a crate of tea into the sea, and meet live 18th-century characters. This tour makes learning hands-on. It’s a fun way to discover an important part of American history.


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#8 – Massachusetts Institute of Technology Public Tour

An insightful tour for technology buffs

Massachusetts Institute of Technology Public Tour

  • $
  • 70 minutes
  • Tour one of the top universities in the US
  • Learn about innovative research in math, science, and technology

Boston has several important universities that are world-renowned for their innovative research. The Massachusetts Institute of Technology (MIT) is one of them. Take a student-led guided tour of the famous MIT campus and explore this institution’s great achievements.

Visit Kendall Square, see the Great Dome, and admire this beautiful campus stretched alongside the Charles River.

Learn about cutting-edge research in math, science, and technology. Hear about the school’s alumni, including astronaut Buzz Aldrin and world-famous architect, I.M. Pei.


#9 – Boston Sunset Cruise

A great activity for couples

Boston Sunset Cruise

  • $$
  • 90 minutes
  • See the top Boston attractions from the water
  • The cruise is fully narrated

If you’re looking for romantic Boston excursions, book a sunset cruise and end your day taking in the breathtaking views of the sun setting over the Boston skyline.

Cruise through the Boston Harbor and listen as your tour guide provides information on the sights you’re passing.

A highlight of the tour is watching the USS Constitution perform its sunset serenade. This is when the boat cannon fires and the flag lowers to signal the end of the day. From your position on the boat, you’ll be able to watch this nighttime ritual with unobscured views.


Editor’s Tip: Check out all the top places in Boston before you lock in your itinerary.

#10 – Boston 90-Minute Historic Sightseeing Cruise

A fun way to see the city

Boston 90-Minute Historic Sightseeing Cruise

  • $$
  • 90 minutes
  • A fully narrated boat tour
  • A combination history and sightseeing tour

Are you looking for unique Boston history tours? With this sightseeing cruise, you’ll learn about Boston’s fascinating history while traveling through the picturesque Harbor Islands National Park Area.

Enjoy wonderful views of the Boston skyline as you take in the fresh open-air. Learn the highlights of American History and hear tales of the Revolutionary War. Pass the nation’s oldest continuously manned lighthouse and the city’s extravagant waterfront properties. This tour is fun for all ages.


#11 – Whale Watching Cruise from Boston

An amazing tour for ocean enthusiasts

Whale Watching Cruise from Boston

  • $$$
  • 3.5 hours
  • Professional researchers on whale populations narrate your trip
  • Ride on a fast and comfortable catamaran

Leave the city of Boston behind on a high-speed catamaran and set off for a three-hour whale-watching cruise. See Humpback, Finback whales, Minke Whales, and other marine animals up-close.

Catamarans provide a great way to see the ocean’s most interesting creatures. There are three outside decks that provide very spacious viewing platforms and optimal visibility. Inside you’ll find cushioned seating, tables, and a snack and beverage counter.


Editor’s note – These are the 15 most beautiful beaches in Boston!

#12 – Boston: 2.5-Hour City View Bike Tour

A great tour for active travelers

Boston: 2.5-Hour City View Bike Tour

  • $$$
  • 2.5 hours
  • A great introduction to Boston
  • Helmets and a water bottle are included

On this Boston sightseeing tour, you’ll cruise through the city on wheels. Explore the highlights of the city as you follow your cycle tour guide around Boston’s most scenic sites. Popular areas include the Boston Common, Copley Square, and the Charles River Esplanade.

Travel from the busy streets of downtown, to the serene paths on the outskirts of the city. You’ll learn about Boston’s past and present as you pass important monuments, landmarks, and historical buildings. This tour is fun for all ages.


#13 – Boston: History Tour of Cambridge, Concord, and Lexington

The ultimate history tour

Boston: History Tour of Cambridge, Concord, and Lexington

  • $$$
  • 4 hours
  • Follow the Battle Trail of the American Revolution
  • Visit the sites that changed the course of American history

Explore important historical landmarks just outside Boston as you follow in the footsteps of George Washington.   

You’ll visit the Cambridge Common, where Washington took command of the Continental Army. Stand on the Lexington Green, the area where American soldiers stood their ground against English soldiers. Travel to the Old North Bridge, where the American farmers fired the “shot heard round the world”.

This history tour takes you on a journey to the top sites associated with the American revolution.


#14 – Historic Pub Crawl Tour along the Freedom Trail

The best Boston pub crawl

Historic Pub Crawl Tour along the Freedom Trail

  • $$
  • 2.5 hours
  • This tour is for guests 21 years or older
  • Beer themed walking history tour

Take a good old fashioned pub crawl and learn about American history while enjoying some local Boston brews. You’ll visit four historic Boston taverns – each dates back to at least the 1800s, with several dating back even further.

Hear stories about Boston’s rebellious past from your knowledgable tour guide. Learn the hidden history of Boston, including the importance of beer in the founding of America. 


#15 – Boston’s Beacon Hill Guided Photography Walking Tour

The ultimate tour for photography fans

Boston's Beacon Hill Guided Photography Walking Tour

  • $$
  • 1.5 hours
  • Get the best Instagram shots
  • Learn valuable photo skills

Take a tour through one of Boston’s most scenic neighborhoods, Beacon Hill. Follow a professional photographer tour guide and learn how to capture the most stunning pictures possible.

Visit Acorn St. and Louisburg Square, two of Boston’s most picturesque areas. Photograph red brick buildings and quaint cobblestoned streets lined with old fashioned gas lamps. You’ll learn skills you can use anywhere in the world.


#16 – Boston’s Back Bay Wine Tasting Guided Walking Tour

One of the best tours in Boston for wine consumers

Boston's Back Bay Wine Tasting Guided Walking Tour

  • $$$$
  • 2 hours
  • Small-group tour limited to 12 people
  • Wine tasting and walking tour

Experience the best of Boston’s wine scene as you visit two of the Back Bay area’s finest restaurants. Learn the history of this charming Boston neighborhood as you sip on delicious wine and tasteful, local food pairings.

An expert, certified wine sommelier will lead your tour and entertain you with information on wine history, wine selection, and Boston’s culinary scene. You’ll leave this activity in good spirits to continue touring Boston.


#17 – Welcome to Boston: Private Tour with a Local

A fun personalized tour

Welcome to Boston: Private Tour with a Local


  • $$
  • 2-6 hours
  • Discover the city with a local
  • Enjoy a 100% personalized tour

For a great introduction to the city, take a private, personalized tour with a local guide. You’ll receive a warm welcome to the city and learn lots of useful information that will help you make the most out of your stay.

Learn insider tips, including the best places to eat, drink, and shop. Your walking tour will be completely personalized to meet your interests. Whether you wish to explore Boston’s history, sports culture, or food scene, you get to decide the theme!



Boston is a city that overflows with history, culture, and character. There’s so much to see and do, which is why tours are a great option. They allow you to discover the city with a local and provide interesting insights into the heritage of the city

There are so many options to choose from, with prices to suit all budgets. Whether you fancy a history tour, an outdoor activity, or an alcohol-fueled excursion, you’ll find what you’re looking for.

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About the Author Nicola Smart

Gin lover. Coffee addict. Nicola has traveled the world for 7 years and is a staff writer for Hotel Jules. Born in London, Nicola first got the taste of travel studying abroad in Barcelona. Since then she's been hooked - traveling the world non-stop. Passionate about green travel and vegan lifestyle, Nicola spends more of her free time staring at maps wondering where she will head to next!