The 19 Best Walking Tours in Boston

a historical actor leading a walking tour in Boston
Posted: 6/10/19 | June 10th, 2019

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 amazing 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!

The Best Free Walking Tours in Boston

the downtown skyline of Boston, Massachusetts
1. Free Tours By Foot
Free Tours by Foot is one of the biggest an 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 over 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!

2. 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.

3. 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 and fills up fast, so be sure to get there early as there is often a wait (especially on weekends).

30 Germania St. Tours occur roughly every 40 minutes between 10am and 3pm Monday-Thursday, 10am-5:30pm on Fridays, and 10am-3pm on Saturdays.

4. 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.

5. 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

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

6. Context Travel
Context is one of my favorite walking tour companies. It offers comprehensive history, food, and cultural tours in cities all around the world — including Boston! There are over a dozen private and guided tours in the city, and while they are not cheap, they are worth every penny. All of their guides are experts in their respective fields, which means any and all of your questions will be answered. If you’re looking for a serious and professional tour, this is it. Tours from $85 USD per person.

7. Cambridge Historical Tours
Cambridge 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 $20 USD per person.

8. Intrepid 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 both history and food tours (as well as one that combines both), though I think the most interesting one is the Bowling and Bites tour, a food trek through East Boston that ends in bowling and billiards! Tours from $46 USD per person.

9. Bites of Boston
Bites of Boston offers three 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 $65 USD per person.

10. 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, highlighting the most Insta-worthy shots the city has to offer. Tours are available year-round, as well, letting you embrace the colors of each season. Tours from $40 USD per person.

11. 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. Check their schedule for availability as tours only occur between April and October.

12. Boston Pizza Tours
Boston Pizza Tours organizes two tasty tours that will take you around town to sample some of Boston’s best pies. The Historic Taverns tour goes a step further, taking you to some of the oldest taverns in the city — as well as the oldest tavern in the country! The best part? You’ll be enjoying a slice and a pint in the same taverns as Paul Revere and Sam Adams! Tours from $44 USD per person.

13. City Wine Tours
This wine tour combines the best wines Boston has to offer with delicious food at some of the best restaurants in town. They have tours for different neighborhoods, and you can also book private tours and events if you’re looking for something special. Tours from $75 USD per person.

14. Trademark Tours
Trademark Tours has put together a great tour of Harvard (led by Harvard students), as well as ones of MIT (led by MIT students) and the Freedom Trail. They are much more affordable 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 $12 USD per person.

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
Find a cheap flight by using Skyscanner or Momondo. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is being left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use as they consistently return the cheapest rates for guesthouses and cheap hotels. I use them all the time. My favorite place to stay is:

  • HI Boston – This hostel is in a great location, has its own coffee bar with lots of space to hang out, and also has female-only dorms. It’s really secure and the staff are great too. It’s the best hostel 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. I’ve been using World Nomads for ten years. My favorite companies that offer the best service and value are:

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 travel — and I think they will help you too!

Looking for more information on visiting Boston?
Check out my in-depth destination guide to Boston with more tips on what to see and do, costs, ways to save, and much, much more!

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