THE 14 best walking tours IN BOSTON

Last Updated: 9/13/21 | September 13th, 2021

I love Boston — and not just because I was born there.

There are tons of free things to do in Boston, enough to keep any visitor thoroughly entertained. It’s also a historic city whose success (and survival) was tied to the very existence of America itself.

With such historical significance, it should come as no surprise that I’ve always found the city fascinating (I studied history in college after all).

Boston’s roots stretch back to the 17th century when it was founded by Puritan colonists from Europe. It was a devout settlement, with enforced church attendance and marriage (persecution of sinners was equally enforced).

The city was home to one of the first schools in America, as well as the very first college: Harvard. The settlement grew in importance, with its most significant role being during the American Revolution.

No single blog post can do Boston — and its complex and important history — justice. For that, you’ll need to visit!

To help you make the most out of your next trip to “Beantown,” I’ve put together this list of the best walking, food, and photography tours. Boston is home to tons of incredible free and paid walking tours that will give you a much better overview of the city and its historical contributions to modern-day America.

Whether you’re a budget backpacker looking to learn something new or a history buff ready to test your expert knowledge, Boston will have a walking tour for you!

Best overall Tour

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Urban Adventures
Urban Adventures is a branch of Intrepid Travel, my go-to company for multiday excursions. Their urban Adventures division runs tours in almost 100 countries around the globe, including some fun tours in Boston.

They have history and food tours (as well as one that combines both). The Boston history and Highlights tour is a great place to start as it gives a nice overview of the city. tours from $46 USD per person.

Best free Tour

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Free tours by Foot
Free tours by Foot is one of the biggest and best free walking tours out there. I’ve been on their walking tours all around the world and always come back having learned something new. They have half a dozen different tours around Boston, though I think the freedom trail tour is the best place to start. If you’re looking for something more unique, be sure to check out the Beacon hill crime tour!

While those may be the best free and paid tours in the city, Boston has a lot more to offer — no matter your interests! here are 13 other insightful and educational tours in the city that are worth checking out:
 

The best free walking tours in Boston

1. GPS My City

If you’d rather do a self-guided tour on your own time, this app is a great resource and will help you explore the city at your leisure. There are over a dozen different routes offered, and you can mix and match all the destinations to make your own tour too. This is a good option if you don’t want to commit to a three-hour walking tour but still want to see some of the sights.

2. Sam Adams Brewery Tour

If you’re the sort of traveler who often gets thirsty on your tours, then this might be the one for you! The Sam Adams Brewery has a free tour of its famous brewery, and it includes a few samples to quench your thirst (you have to be over 21 of course). The tour is offered daily and fills up fast, so be sure to get there early as there is often a wait (especially on weekends). The brewery also has a Bier Keller experience that brings together two age-old pleasures: beer and cheese!

30 Germania St. open Monday to Friday from 2pm-8pm, Saturdays from 12pm-8pm, and Sundays 12pm-6pm. tour experience tickets are released one week at a time. If a date is sold out online, you can still try to get on a tour at the door as they save some tickets for people who show up.

3. state house Tour

The Massachusetts state House, home to the governor and government of Massachusetts, has free tours during the week. You can join a guided tour or take a self-guided tour if you’d rather go solo. tours last 30-45 minutes. You’ll learn about the building, which was built in 1798 and went way over budget, as well as how the state government functions. If you’re a fan of architecture or politics, this brief but informative tour is worth checking out.

24 Beacon St. tours are available Monday-Friday between 10am and 3:30pm. To organize a free tour, call +1 617-727-3676. (Currently closed for COVID).

4. freedom trail Self-Guided Tour

For a self-guided tour of the freedom Trail, use this free map. It has all of the major sites and some suggested itineraries based on how long you want to spend exploring the city. If you’re looking for a simple self-guided option that covers all the major historical sites, look no further!
 

The best Paid walking tours in Boston

While free tours are a great place to start, for a more in-depth and specialized tour, you’ll need to pay some money. here are some that are well worth the price!

5. Boston historical Tours

Boston historical tours does a great job of blending rigorously researched history and humor, creating an entertaining and informative tour for all ages. They have a few different walks worth checking out, including the freedom trail tour and the evening Ghost Tour. The prices are reasonable (especially if you’re a group) and their costumed guides are top-notch.

Tours from $25 USD per person.

5. Bites of Boston

Bites of Boston offers two different food tours around town, each in a distinct neighborhood. Each lasts a few hours, giving you a nice range of culture and food from some of the best restaurants in town.

Tours from $74 USD per person.

7. PhotoWalks Tours

If you’re a shutterbug looking to snap a few shots, this is the tour for you. PhotoWalks tours offers half a dozen different photo tours around Boston, with fascinating historical commentary highlighting the most Insta-worthy shots the city has to offer and including creative photo tips. tours are available year-round, as well, letting you embrace the colors of each season.

Tours from $40 USD per person.

8. On location Tours

This is the perfect tour for movie buffs. On location tours will take you to all the major filming locations from popular movies and TV shows shot in Boston, including The Departed, good will Hunting, Amistad, and Cheers.

Tours from $31 USD per person if you go in a group of 3 ($45 USD for groups of 2). check their schedule for availability as tours only occur between April and October.

9. Boston Pizza Tours

Boston Pizza tours organizes a tasty tour that will take you around the North end to sample some of Boston’s best pies. It includes visiting 5 freedom trail sites, water, three full-size pizza slices, and a cannoli for dessert.

Tours from $49 USD per person.

10. trademark Tours

Trademark tours has put together a great tour of Harvard (led by Harvard students). They are much more inexpensive than some of the other companies, making this a good middle-of-the-road option for anyone on a budget (as well as for families).

Tours from $19.50 USD per person.

11. Boston By Foot

Boston By Foot is a local non-profit that organizes historical tours around the city. They have almost two dozen tours and events on offer, from the classic freedom trail to literary tours to river cruises that focus on the city’s architecture. tours are run by enthusiastic local volunteers who are well-trained and knowledgeable about the city and its past.

Tours start at $15 USD per person.

12. urban Adventours

If a walking tour isn’t your thing, or you want to cover more ground in less time, consider a bike tour. urban Adventours offers bike rentals as well as 4 different tours of the city, including a city view tour, a tour along the Charles River, and a tour of the emerald necklace park system.

Bike rental starts at $30 USD for 2 hours and tours cost from $60 USD.

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Whether you’re a history buff, a foodie, or someone just looking to explore one of the best cities in America, Boston will have a walking tour to suit your needs — no matter your budget!

Book Your trip to Boston: Logistical tips and Tricks
Book Your Flight
Use Skyscanner or Momondo to find a cheap flight. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned. start with Skyscanner first though because they have the biggest reach!

Book Your Accommodation
You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels. My favorite hostel to stay in the city is HI Boston.

For more hostels, check out this post on the best hostels in the city.

If you want to know the best neighborhoods to stay in, here’s my guide to all the best areas in town.

Don’t forget travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

SafetyWing (best for nomads)

World Nomads (most comprehensive)

Insure My trip (for those over 70)

Medjet (for additional evacuation coverage)

Looking for the best companies to save money With?
Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Wat more information on Boston?
Be sure to visit our robust destination guide to Boston for even more planning tips!