Top Massachusetts Walking Tours

We are a SMALL, LOCAL business, PLEASE consider supporting us directly at our website as this reseller takes a 25% commission on all bookings. BUT FIRST, DESSERT! Do dessert before dinner when you join us for Cocktails & Cannoli, an all inclusive walking food tour of Boston’s North End. Skip the infamous lines to taste delicious drinks and classic cannoli, and sample the best sweets the North End has to offer. Not to mention the Paul Revere House and Old North Church along the way! To top it all off, our local tour guides will sprinkle in fascinating historic knowledge, fun cultural facts, and culinary tidbits.

Other than expensive private tours, this is the only available tour of the Freedom Trail on which tour goers will view all 16 official sites of the Freedom Trail in a single tour. For the Boston visitor with the busy itinerary, this is the most economical option in terms of time and money to check the Freedom Trail off of your list. Our guides have decades of experience in tourism, history, and performing, let them ensure that your experience of the Freedom Trail is everything that it can be!

Enjoy this private half day walking tour with your own official tour guide and explore the vibrant city of Boston. Get ready to explore the most emblematic and nicest spots in this wonderful city. You will meet the guide in a central point or in your hotel centrally located in Boston who will take you on this private tour. You will be able to visit The Freedom Trail, Faneuil Hall Marketplace, Quincy Market and many more fantastic sites in the home of the first subway system of the United States. Once we start the tour, we offer you to visit, amongst other sites Trinity Church Boston Common Massachusetts State House Boston City Hall HarborWalk Faneuil Hall Marketplace North End - SAVE COVID-19 SAFE - As this is a private tour we take care of maintaining social distance

Boston is a city known for its significant role in shaping American history and its contribution during the American Revolution. Alongside this historical significance, Boston has long been known as one of the leaders in the chocolate movement. In fact, the first chocolate shop in the colonies opened in 1740 in the North End of Boston with a "drinking chocolate". And we didn't stop there! Boston takes pride in the creation of several iconic desserts that we'll sample during our chocolate-filled journey through the city! As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Get to know Boston through its food on this small-group walking tour limited to 12 people. With a guide, you sample seafood, Italian dishes, and other fare as you explore the city's North End neighborhood. Along the way, learn about the history of the area.

Meander along the cobblestone streets and narrow brick alleyways of Boston's Historic North End while sampling some of the best food the city has to offer. Delve into the heart of the city's best Italian food while your guide takes you off the beaten path, to places only the locals shop at. Let your local North End guide navigate the winding streets in Boston's oldest neighborhood to show you the hidden gems you wouldn't find on your own. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Meet up with a guide from Lokafy for a custom walking tour of Boston that’s like having a local friend to show you around the city. Before meeting up, connect with the guide by phone or chat to customize the experience to your interests, whether you’re curious about the coolest Boston neighborhoods or searching for the best local restaurants.

Experience the rich history of Boston through its local craft beer! Join the Boston Brew Tours, as we explore behind-the- scenes tours of craft breweries while tasting local beer and deliciously paired food! • Enjoy a delicious beer paired meal • Sample a variety of up to 16 beer styles • Take a VIP access tour through Boston's finest local breweries

Travel back in time to colonial New England on a 90-minute historic walking tour. With a length of just 1.2-miles, you can enjoy the experience without breaking a sweat. Your costumed and in-character guide gives you an immersive understanding of life during America’s infancy. Hear exclusive stories about the country’s Founding Fathers and discover iconic historical sites. 

The history of Salem, the notorious site of some of the historical witchcraft trials, is shrouded in misconceptions. Unravel the mystery of the town's past on this ghost tour that takes you to all of the main haunted attractions in Salem while offering insight into the town's history through research and eyewitness accounts.

Treat yourself to a quintessentially Bostonian experience with this Fenway Pub Crawl. Meet your expert guide just outside Fenway Park and set off on a pub crawl to four beloved bars along Lansdowne Street. Enjoy local beers as you learn all about the Red Sox and Boston’s baseball history. Select the Happy Hour option for 4 pints of your choosing, or opt to buy your drinks as you go.

What makes this tour different is that instead of walking the Freedom Trail geographically – starting at one end and following it to the other – we let the escalating action of the American Revolution guide us through the crooked streets of Boston. The sightseeing is synchronized with and unfolds to the storytelling. There’s a lot less emphasis on dry facts and dates and a lot more on the passions, personalities, and psychologies driving the events; recreating the drama and recapturing the energy that invented America. It's not only much more enjoyable it's also the most effective way to explore the city and relive the history. The entire experience has been built with the aspirations and anxieties of a fellow tourist in mind: the groups are kept small so you aren't herded around; we cover both the major sights and the hidden gems; extensive visual aids and props help you grasp the material, and you'll traverse all original neighborhoods getting a sense of the modern city as well. 

Tour like a Local with a Private Guide! Treat yourself to some of the best pizza in Boston on this Private North End History & Pizza Walking Tour through Boston's "Little Italy". See the sights as you walk in the footsteps of Revolutionary Patriots like Paul Revere, Samuel Adams and George Washington. During this fun history walk you’ll see FIVE Freedom Trail sites, plus enjoy THREE different slices from some of Boston’s very best Pizzerias. Pizzerias on tour can rotate from day to day, and may include – a slice named in the “Top 25 Best” in America by a Famous Food Critic, a slice from Boston’s oldest Pizzeria with a brick oven from 1883, a “Secret Underground” spot for grilled flat-bread Pizza, or from a restaurant named one of the “Top 10 Best” Italian Restaurants in the World! Bonus Stop at Modern Pastry to finish with a FREE cannoli! See top Boston sites including Paul Revere House, the Skinny House, Bunker Hill Monument, USS Constitution, and Copp's Hill Burying Ground.

Enjoy some of the best pizza in Boston on this walking food tour. Stroll through the city’s oldest neighborhoods, including, appropriately, Little Italy on the North End. Walk along the Freedom Trail that leads to 16 historically significant sites, like Paul Revere House, Old North Church, and the USS ‘Constitution,’ to name a few. Visit some of Boston's best pizzerias and enjoy a slice at each. It’s a fun and flavorful way to get to know Boston.

Calling all ballpark foodies! Don’t miss this unique tour highlighting delicious ballpark eats in the shadow of historic Fenway Park. In the past several years, Fenway neighborhood’s food scene has experienced a flavor explosion. No longer just a destination for Red Sox games, now there’s true culinary talent in its midst. On this exciting food tour, we’ll visit the new Time Out Boston Market food hall for a coffee specialty drink then chow down on the best “American” ballpark eats and visit a variety of iconic restaurants around Fenway Park. We’ll learn about the history of the famous Citgo sign and the Green Monster while munching on the best eats in town from scallion pancake sandwiches to pizza and brown butter ice cream. Discover the Fenway-Kenmore Square neighborhood with a local guide and fall in love with this unique area of Boston.