The Best Tours in Boston, Massachusetts

From History to Food: The 15 Best Boston Tours You Have to Take!

History is in every cobblestone step of Boston. From the lanterns hung at Old North Church to alert that the British were coming to the haunted halls of the famous Omni Parker House Hotel, this city has so many stories to tell. It’s no wonder one of the best things to do in Boston is to go on a tour that tells you all about its many historical landmarks. 

But there’s more to Boston than history. A foodie will love spending an afternoon touring the many top dining spots of the city’s beloved North End. And a photography lover would be hard-pressed to find a more beautiful place than Boston’s Beacon Hill, featuring some of the most photographed spots in the United States. And any sports fan would adore meeting the famous Green Monster of Fenway Park.

With so many things to see and do, how do you know which tour is right for you? We’ve compiled our list of the absolute best tours in Boston to help you get started. Stick to these fun and unique Boston tour recommendations, and there’s no doubt you’ll have an amazing time exploring this historic city!

The 15 Best Tours in Boston, MA

1. Capture the Memories of Your Trip with a Photography Walking Tour

Best Tours to Book in Boston: Photography Walking Tour

What’s better than a knowledgeable tour guide? A knowledgeable tour guide who is also an incredible photographer! When you take a photography walking tour of Boston, you’ll be guided throughout this stunning city by someone who can help you capture every moment. 

You’ll follow a carefully planned route to see some of the biggest cultural (and more photogenic) landmarks in the city. You can book either a group tour or a private tour, but either way, you’ll get a one-of-a-kind way of looking at Boston. 

Cool Tours to Book in Boston: Photography Walking Tour

Along the way, your photographer will capture shots of you and your party as you explore Boston. As you learn about the city’s history, you’ll also hear tips and tricks to boost your own photography skills. Once the tour comes to an end, your guide will lead you to a cozy cafe to review your photos and pick out the ones you like. 

You’ll send yourself a postcard with your favorite shot, and you’ll also receive 15 to 20 professionally-edited images in five to 10 days after your tour. This unique Boston tour is a great way to collect beautiful souvenirs of your journey to this historic city.

Try the Boston Photography Walking Tour

2. Eat Boston’s Most Famous Dishes on a Bites of Boston Tour

Fun Tours to Book in Boston: Most Famous Dishes on a Bites of Boston Tour

Learning about Boston’s history is always fun. But learning about the city’s history while eating your way through it is even better.

The Bites of Boston Tour is one of the best Boston tours because you’ll learn about the city in a unique way. You’ll uncover why Boston’s famous foods are so famous in the first place. Where and why was the Boston Cream Pie created? What’s up with the Beantown nickname? And what’s really the best place to get chowder in the city?

You’ll dive into the history of these dishes over the course of a three-hour eating tour of Boston. You’d better arrive on an empty stomach because there’s plenty to dine on throughout the journey. 

You’ll stop by historic restaurants, pubs, and more, where Boston’s best foods were born. You can also upgrade your tour to include a beer tasting at two of Boston’s most beloved taverns.

Take the Classic Bites of Boston Tour

3. Admire the Historic Architecture of the City

Cool Tours to Book in Boston: Historic Architecture of the City

Boston is a city like no other, and the architecture plays an essential role in creating that feeling. No matter where you look, you’ll find buildings that feel lost in time, bringing you back to the days of the Revolutionary War. Boston’s history is true American history, and going on an architecture walking tour is a fantastic way to learn more about the people and places that built this country.

You’ll stroll along the historic Freedom Trail, where you’ll walk from landmark to landmark between the famous Faneuil Hall to the beloved Boston Common. Although you’ll hear plenty of historical facts, you’ll also get an in-depth look at the city’s architecture. 

As you stroll the cobblestone streets, you’ll see sights like the Park Street Church, a congressional church that was among the first in the country to advocate for social justice topics like the women’s rights and anti-slavery movements, and the Old Corner Bookstore, the oldest commercial building in Downtown Boston. You learn about the buildings and the stories that happened within their walls.

Learn History & Architecture on a Walking Tour

4. Walk the Freedom Trail with an In-Character Guide

Unique Tours to Book in Boston: Walk the Freedom Trail with an In-Character Guide

There are many ways to experience the famous Freedom Trail, but the Freedom Trail Walk into History Tour is one of the best tours in Boston. This tour, brought to you by the official Freedom Trail Foundation, is an experience like no other!

Your period-costumed guide will take you through the Freedom Trail, where you’ll walk in the footsteps of great American patriots like Crispus Atticus, John Quincy Adams, and many more. Eleven of the 16 official Freedom Trail historic sites are featured on this 90-minute tour.

Fun Tours to Book in Boston: Walk the Freedom Trail with an In-Character Guide

See Paul Revere’s final resting place at the Granary Burial Ground, learn about the history of the oldest public school in the US, and explore America’s first public park, the Boston Common. Your knowledgeable guide will help you feel like you were truly there at the start of the United States. 

Walk along Boston’s Freedom Trail

5. Tour One of the Most Beautiful and Historic Theaters in the Country

Boston’s Theater District is home to a number of historic theaters that put on can’t-miss shows. Among them is the beloved Boch Center Wang Theatre. One of the coolest tours in Boston allows you to go behind the scenes at this cultural hub.

The Boch Center Wang Theater Behind-the-Scenes Tour takes you inside this marvel. As soon as you enter this theater, you’ll take in a breathtaking sight. You’ll be greeted by a massive chandelier soaring high above you on the ornately-decorated and mural-filled ceiling, which is held up by gilded marble columns. You’ll know you’re in for one incredible tour as soon as you see this sight!

On this one-hour guided tour, you’ll learn about how the theater, listed on the National Register of Historic Places, came to be and why it’s designed the way it is. You’ll even get the chance to stand on the iconic stage, which once held such incredible acts as Ella Fitzgerald, Queen, Liza Minnelli, and Elton John.

Visit the Historic Boch Center Wang Theatre

6. See the Boston Sights That You’ve Seen in Your Favorite Films

Boston Tours You Have to Take: Boston Sights that You've Seen in Your Favorite Films

Hollywood is not the only place where you can step into the shoes of your favorite actors. Boston has been home to a number of beloved shows and movies. You’ll be able to see all these iconic spots on the Movie Mile Walking Tour, one of the most unique Boston tours.

On this interactive tour, a local actor will take you to both famous and little-known filming locations of your favorite shows and movies. You’ll sit on the park bench from Good Will Hunting, see where Jack Nicholson hung out in The Departed, and even grab a drink at the original bar from Cheers.

Boston Tours You Have to Book: Boston Sights that You've Seen in Your Favorite Films

Along the way, you’ll uncover insider secrets from the sets of Fever Pitch, Legally Blonde, Mystic River, and more. It’s the perfect tour for a film lover on a Boston vacation.

Live Out Your Own Filmic Fantasy

7. Take a Historical Tour of one of Boston’s Most Beautiful Locations

Best Tours to Book in Boston: Beacon HIll

When we think of Boston’s history, we often think of the Revolutionary War first. We picture the Boston Massacre or the Boston Tea Party, but Boston has played a role throughout America’s greatest conflicts. And you can take a walking tour that allows you to learn about the part Boston played in the Civil War.

This tour takes you through Beacon Hill, one of the most scenic and historic areas of Boston. On this Beacon Hill Tour, you’ll walk the Black Heritage Trail, which explores the lives of African-Americans in Boston in the 19th century. 

Cool Tours to Book in Boston: Beacon Hill

You’ll see homes on the Underground Railroad, visit the African Meeting House, and learn about the struggle for equality throughout the area. You’ll be just blocks from the wealthiest of Boston, but you’ll hear about a very different reality from the lives these Bostonians are living.

There are many historical tours in Boston, but this Boston tour is one-of-a-kind. The struggle of African-American Bostonians is little discussed and even less understood. On this tour, you’ll dive deep into a reality that deserves a spotlight.

Explore Hidden Landmarks in Beacon Hill

8. Go on a Pub Crawl With a Ghostly Theme

Unique Tours to Book in Boston: Pub Crawl

Taverns have long played a role in the history and culture of Boston. And with the Haunted Pub Crawl, you’ll be able to walk in the footsteps of the Founding Fathers as they gathered, drank, and planned a new country.

This unique Boston tour takes you to the most notoriously haunted pubs and restaurants of Beantown. You’ll grab a drink as you listen to stories of the Americans who once drank there, from Samuel Adams to John Adams to Paul Revere. 

You’ll also hear more sordid tales of the city. Not all historical figures are quite so friendly. You may or may not see the apparitions of these Boston residents, but you’ll surely feel their presence as the hair on the back of your neck stands up hearing these ghastly tales. You’re going to need more than one drink of liquid courage to spend the evening hearing these incredible stories!

Experience a Haunted Pub Crawl

9. Journey into Boston’s Underbelly on a Trolley Tour

Boston Tours You Have to Take: Ghosts and Gravestones Tour

Sure, you could go on a sightseeing tour, but the Ghosts and Gravestones Tour is one of the coolest tours in Boston. Not your average tour, this excursion is considered a “frightseeing” tour. 

On this unique Boston tour, you’ll hop aboard a trolley with a costumed guide who will do their best to scare the pants off you. Don’t worry – they’re pretty friendly, even if the ghosts you may encounter aren’t so much.

On this 90-minute tour, your 17th-century gravedigger guide will tell you Boston’s most gruesome tales. You’ll learn about the story of the Boston Strangler, be guided around the city’s most haunted areas, and hear tales of those who performed the most sordid acts imaginable, often in plain sight.

You’ll also be taken to Copp’s Hill Burial Ground and Granary Burying Ground, Boston’s oldest cemeteries, and visit the gravesites of John Hancock, Paul Revere, and many others. You never know just what you might see on this tour, which is as informative as it is spine-chilling.

Venture to Boston’s Burial Grounds

10. Tour the North End’s Best Dining Spots

Best Tours to Book in Boston: North End

Boston’s North End is arguably home to some of the best food in the country. From famous cannolis to fresh seafood dishes, this area of the city is a foodie’s paradise, which is why the North End Secret Food Tour is one of the best food tours in Boston.

You’ll walk along this charming area, filled with quaint and colorful restaurants and gastropubs. On this three-hour tour, you’ll learn about the area’s roots as you’re taken to seven stops. What treats are awaiting you? You can expect fresh pasta courtesy of Boston’s Little Italy, pizza eaten in the shadow of the famous Old North Church, an Italian sandwich like no other, and so much more.

Your guide is as knowledgeable about Boston’s history as they are about the city’s best food. Expect a tour filled with little-known facts and even littler-known Boston treats.

Discover Boston’s North End

11. Journey Through the History of ‘America’s Most Beloved Ballpark’

Cool Tours to Book in Boston: Fenway Park

Speaking as someone who isn’t even a baseball fan, I marvel at Fenway Park every time I see it. It’s the oldest MLB ballpark, and there’s so much history in every square inch of this beloved stadium. A Walking Tour of Fenway Park is one of the best Boston tours and something you truly cannot experience anywhere else.

On a one-hour guided tour, you’ll explore the historic grounds of this Boston icon, home to the Boston Red Sox. You’ll learn about the history of this stadium, which is over 100 years old, as you see Pesky’s Pole, sit atop the famous Green Monster, and take in the views of Boston from the Roof Deck. You’ll then tour the Fenway Park Living Museum, which is home to more than 170,000 stadium artifacts and 150,000 photographs. 

You can take either a public or private tour, but you do get access to features with a private tour you won’t get with a public one. With this upgrade, you may visit a number of additional locations, like the famous Red Seat, the Visiting Team Clubhouse, or the Green Monster Scoreboard.

Get Up-Close Access to Fenway Park

12. Take a One-of-a-Kind Tour on Both Land and Water

Best Tours to Book in Boston: Boston Duck Tour

What’s the best tour in Boston? Many locals and visitors alike will tell you that there’s nothing quite like a Boston Duck Tour. You’ll climb aboard a World War II-style “Duck” that takes you through the streets of Boston and into the Charles River.

On this 80-minute tour, you’ll be led by a “ConDUCKtor,” who will tell you all about the history of the most significant landmarks of the city. You’ll see the State House, Bunker Hill, the Boston Common, Copley Square, Newbury Street, Quincy Market, and more. 

You’ll hear little-known facts about these iconic locations before you head to the Charles River for the splashdown. From the water, you’ll take in one of the best views around both Boston and Cambridge. This tour is one of the best Boston sightseeing tours available, and you’ll love every minute aboard your Duck.

Book the World-Famous Boston Duck Tour

13. Step Back in Time During an Interactive Tour

Best Tours to Book in Boston: Boston Tea Party Ships and Museum Interactive Tour

There are many great tours of Boston, but few allow you to get in on the fun as much as the Boston Tea Party Ships and Museum Interactive Tour. This tour will enable you to relive the Boston Tea Party with live actors, 3D holograms, and replica ships.

When you arrive, you’ll receive a handbill from one of the colonist actors, telling you which part you’ll play. You never know what you might get. Then, you’re off to start a revolution.

In the meeting house, you’ll learn all about the fateful night of December 16, 1773. You’ll then get your own disguise before you begin the march to Griffin’s Wharf. It’s up to you and your fellow revolutionaries to throw crates of tea into the sea. You can also explore the replica ships, designed to look like the original ships from the Boston Tea Party. 

Inside the museum, you’ll watch British soldiers and colonists fight before your very eyes. You’ll then head into a giant wraparound theater where you’ll watch the battle play out.

Become a Part of the Boston Tea Party

14. Satisfy Your Sweet Tooth on a Donut Tour

Cool Tours to Book in Boston: Donut Tour

What do you think of when you think of Boston food? Maybe you think of the Boston Cream Pie. Or perhaps a lobster roll springs to mind. But how about donuts?

If you’ve got a sweet tooth, the Underground Donut Tour is easily one of the best food tours in Boston. From Union Square Donuts to Kane’s Donuts to even more under-the-radar stops, you’ll eat your way around the city donut-style. 

You’ll be led from the Financial District to the Boston Public Market, where you’ll sample donuts alongside apple cider as you learn about the history of this massive market. Then, you’ll head into Little Italy and stop at one of the oldest bakeries in the city for a unique treat. Then, it’s back to the Public Market for even more donuts. 

Be sure to arrive with an empty stomach because you’re sure to want to sample as many donuts as you can. And along the way, you’ll learn even more about Boston’s history, making this tour as educational as it is delicious.

Eat Some of America’s Greatest Donuts

15. Look for Whales off the Coast of Boston

Fun Tours to Book in Boston: Look for Whales Off the Coast of Boston

Prime whale-watching season in Boston lasts from May to October, although you may see some whales outside of these months. But if you are visiting during this prime season, you’ll definitely want to hop on a Whale Watching Catamaran Cruise. Your knowledgeable guide will tell you all about these stunning creatures as you spot them in the water.

You’ll meet with researchers of the Whale Center of New England aboard this three-hour cruise, who will provide expert commentary as you look for humpbacks, finbacks, and minke whales. You may also spot some white-sided dolphins if you keep your eyes peeled.

Unique Tours to Book in Boston: Look for Whales Off the Coast of Boston

With a climate-controlled cabin space and cushioned seating, you’ll be able to search for whales in comfort, even if the weather is getting chilly in Boston. And with a state-of-the-art sound system, you’re sure to hear your guide’s commentary and won’t miss a minute of the whales breaching.

Join a Whale Watching Cruise

There you have it! The 15 best tours in Boston. Do you have any unique Boston tours you’d recommend? Let us know in the comments!

Planning a trip to Massachusetts? Check out our favorite books and travel guides!



  • Jacqueline Gualtieri

    Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California.

    When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes.

    Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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