Best Boston Walking Tours in 2026

Boston , Massachusetts

From $ 5.50

You will go to the best local pizza and cannoli spots, stop by authentic Italian shops and you’ll even get a chance to have a picnic in the Prado to eat the tasty treats you picked up while hearing the story of Prince Pasta. Go at your own pace and schedule, the tour is a smart phone navigated tour on the WalknTours app, meaning you can go anytime. Don’t miss out on our local food and history tour experience that will take you to the most authentic spots in the North End. Along the way you'll hear the history of the North End, the story of its immigrants, Pizza, Cannoli’s and more. Take note: Most shops are open longer hours, but Galleria Umberto is ONLY open for Lunch, from 10:30 to 2:30, and they close often. Please check their schedule. You don’t want to miss this local experience. It starts at Galleria Umberto.

Boston , Massachusetts

From $ 9.75

Explore the gas lit winter wonderland streets of Boston and Beacon Hill as we discover the Christmas tales of Boston's past walking on cobbled stoned alleys. One tour purchase works on up to 4 smart phones. See the Kings Chapel, The Boston Christmas Tree, Beacon Hill, the most photographed street in Boston, the best holiday lights, the oldest hotel in the USA and walk through the gas light, cobbled stoned street winter wonderland. Go anytime, at your own pace, the tour is smart phone guided (GPS navigated) experience narrated by Santa Clause and his rag tag holiday crew.

Boston , Massachusetts

From $ 5.75

Discover the North End, Little Italy's history, Paul Revere, Italian Food, immigration history of the Italians, Irish, Jewish and Africans on this Smart Phone navigated, location aware tour. Go at your own pace. You'll learn about Italian feasts, explore the Copp Burial Ground, and see many spots to eat.

Boston , Massachusetts

From $ 11.99

Are you looking for a way to discover Boston without joining a tour group? Explore at your own pace with this self-guided walking tour. • Find out how the city ignited the American Revolution, led the country in the fight to abolish slavery and, ultimately, saved the Union • Hear from producer Mitch Lapin, a local tour guide and history expert • Do it all in 90 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the app and enter your code. The app displays directions to the starting point, and when you’re in the right place, pop in your headphones, and just tap start. The app has automatic GPS playback, with turn-by-turn directions. It also works offline.

Boston , Massachusetts

From $ 28.00

Explore Boston's rich sports history on foot! Dynasty beginnings to banner nights—experience the legacies that make this town shimmer! Come discover why Boston gets its Title Town reputation with a walk through the Celtics, Bruins, and Patriots' storied histories. Learn the powerful beginnings of each team and how they rose to elite prominence, giving Boston unforgettable record-setting title runs. Follow the Freedom Trail to TD Garden and learn about how America's earliest values overlay with this Title Town's sports legacy and discover the inspirational and complex connections between the city's diverse populations and their accomplished sports teams. Journey from Government Center to TD Garden - along the Champion's Parade Route, through Boston's historic West End via the Freedom Trail, and on to the 'Hub on Causeway' at TD Garden - all while discovering iconic monuments, hidden sports spots, and rich sports history along the way.

Boston , Massachusetts

From $ 30.00

Boston conjures thoughts of Paul Revere, the Boston Massacre, and the start of the American Revolution. Take our walking tour and learn from a certified historian about these famous events that led to the birth of our nation. You'll also learn about Boston's humble beginnings in the 1630s, its growth through the 1600s, and the colonial times of the 1700s. This fascinating tour will discuss many famous citizens, Patriots, and events that molded the city of Boston through its first two centuries. You'll walk through history. You'll walk amongst old buildings. You'll walk in the footsteps of those who yearned to start a new country.

Boston , Massachusetts

From $ 5.99

Solve a murder mystery while exploring Boston’s streets Enjoy a mix of storytelling, puzzles, and real-world exploration Play at your own pace—pause, resume, or replay anytime A fun outdoor activity for couples, families, or groups of friends

Boston , Massachusetts

From $ 6.00

Discover Boston's revolutionary spirit and rich heritage through an immersive audio experience that puts you in complete control of your journey. Unlike crowded group tours that rush you through attractions, this self-guided adventure allows you to pause at monuments that captivate you, delve deeper into stories that intrigue you, and explore hidden corners that traditional tours overlook. Our expertly crafted narration reveals exclusive insider stories, untold historical secrets, and fascinating details that even many locals don't know, all delivered through crystal-clear audio by professional storytellers whose engaging voices bring Boston's past to life. You'll gain authentic insights into the city's revolutionary roots, architectural marvels, and cultural treasures while enjoying the freedom to customize your route, spend extra time at your favorite sites, and discover Boston at a pace that suits your schedule and interests perfectly.

Boston , Massachusetts

From $ 7.99

Walk in the footsteps of America’s revolutionaries with our immersive Boston Freedom Trail audio tour! Unlike crowded tours, this guide brings history to life at your pace, letting you explore iconic sites like Paul Revere’s House, the Old North Church, and Boston Common while uncovering hidden stories and bold personalities that shaped the nation. Hear expert insights, stop and start anytime, and skip the pricey tour guides—just download, plug in, and let history unfold in your ears. Join thousands of travelers who’ve rediscovered Boston’s past like never before—start your journey today! *Download the Shaka Guide app to access the purchased tours*

Boston , Massachusetts

From $ 12.31

Let’s Roam leads the way in app-led adventure hunts! Explore top landmarks and uncover hidden gems, tackling trivia and challenges with your team. Perfect for any occasion – from everyday adventures to bachelorette parties, birthdays, and corporate team-building. Each player selects their role, ensuring a unique and memorable experience!

Boston , Massachusetts

From $ 12.74

Download GuideAlong’s self-guided audio walking tour of Boston’s Freedom Trail and uncover the birthplace of the American Revolution. Step back in time as you visit all 16 historic sites, including Faneuil Hall, the Old North Church, Paul Revere House, and the Bunker Hill Monument. Along the way, hear tales of Paul Revere’s midnight ride, colonial unrest, and the battles that shaped a nation play automatically as you follow the red-brick path through Boston’s historic heart. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. ✅ Stories, tips, and directions play automatically based on your location ✅ Travel at your own pace ✅ Tour offline using GPS. No cell service or WiFi is needed ✅ Suggested itineraries for half, full, or multi-day use ✅ No time limits or expiry, and free updates Purchase one tour per person, or listen together by sharing headphones or a speaker.

Boston , Massachusetts

From $ 12.74

Traverse Boston’s oldest neighborhoods and hear about the lost souls still trapped within—from the poor, perpetually burning victims of a gas explosion in Boylston Station to a spectral woman in the Boston Common who tries to convince children to follow her into the dark. Walk through uneasy graveyards where the bodies have been moved, dug up, or lost altogether, and learn the stories of their unquiet dead. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This is not an entrance ticket to attractions along the route. Check opening hours before your visit.

Boston , Massachusetts

From $ 30.00

Boston already has plenty of tours that focus on the American Revolution. So we created one that focuses on inventions, entrepreneurship, and social change — ways Boston changed the world, both before and after the Revolution. We’ll talk about the importance of the schools and colleges created here in the 1600s; one of the first “clinical trials” conducted in North America, which saved countless Bostonians from smallpox; one of the country’s most impressive Black inventors; the connection between an MIT startup and “The Wizard of Oz”; and women who protested and went to jail to gain voting rights. We’ll also talk about one of America’s first millionaires, whose fortune was built on ice cream and cocktails. If you want to understand what makes Boston unique, and you’re interested in STEM, entrepreneurship, or social change movements, this tour is especially for you! This is an official Innovation Trail walking tour. Next tours on: July 27, 28, 29, 31, Aug 1, 2, 8, 12, 19, 20, 22.

Boston , Massachusetts

From $ 12.31

Let’s Roam leads the way as the top app-led adventure hunt company. Explore the finest landmarks and uncover hidden gems, tackling trivia and challenges along the way. Collaborate with your team or challenge them head-on while discovering new facts and making unforgettable memories. Let’s Roam Adventure Hunts are perfect for any occasion—whether it’s a casual outing, celebratory event like bachelorette parties or birthdays, or corporate team-building adventures. Each participant selects a unique role with personalized challenges, ensuring an engaging experience for everyone involved!