The Best Walking Tours in Boston
I love Boston — and not just because I was born there.
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!
Best Overall Tour
Take Walks
Take Walks is my go-to walking tour company. Their guides are always experts who have in-depth knowledge that other tours don’t. In Boston, they have a detailed Freedom Trail tour that covers the highlights while also providing insider access to Paul Revere’s home. They also run a full-day tour to Salem, where you can learn all about the witch trials. I can’t recommend these tours enough!
Best Free Tour
Tours by Foot
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 of cool tour options to serve any interest. Here are some of my other favorite tour companies in the city:
1. Devour Food Tours
As a foodie, I always try to take a food tour when I visit somewhere. Devour is my go-to company as their tours always feature amazing eats and include tons of interesting information. In Boston, their Freedom Trail & North End food tour lasts three hours and includes stops at six different businesses, including the oldest restaurant in the city. You’ll get to try Italian pastry, as well as local favorites like clam chowder and lobster rolls.
Tours from $89 USD.
2. Cambridge Historical Tours
This company offers some of the best overview tours of Boston. On their Freedom Trail tour, you’ll visit all 16 official sites of the Freedom Trail and dive deep into US history as Boston was a pivotal staging ground for revolutionary activities. You’ll see the resting places of John Hancock, Paul Revere, and Samuel Adams; the city’s iconic Golden Dome; historic Faneuil Hall, and much more! It’s a solid introductory tour to the city and the country.
Tours from $32 USD.
3. The Hahvahd Tour
Founded in 1636, Harvard is the oldest university in the country and one of the most sought-after schools in the world. On this 70-minute tour you’ll get an insider look at this iconic institution. Guides are current students, so you’ll not only learn about the university’s past but also what life is like for students today.
Tours from $22 USD.
4. US Ghost Adventures
If ghosts and the paranormal are your cup of tea, consider taking the Boos and Brews haunted Pub Crawl. On this two-hour pub crawl, you’ll visit four different bars and five haunted sites around the city. You’ll visit a 17th-century graveyard, learn about the life and death of Sam Adams (one of the Founding Fathers), and hear ghostly tales about a haunted hotel.
Tours from $35 USD.
5. 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 runs a 45-minute 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 fills up fast so be sure to book early online. The brewery also has a R&D tour for $5 USD where you can try experimental flavors that aren’t available yet and provide feedback as well as Bier Keller experience that brings together two age-old pleasures: beer and cheese!
The Sam Signature Experience Tour is $10 USD. The Bier Keller tour is $40 USD.
6. 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.
Tours are available Monday-Friday 10am-3:30pm. To organize a free tour, call +1 617-727-3676.
7. Boston By Foot
Boston By Foot is a local non-profit that organizes historical tours around the city. They have half a dozen daily and weekly tours on offer, as well as over two dozen tours that run on a monthly or quarterly schedule (so be sure to book early so you know what tours are available). Tours range from the classic Freedom Trail to literary tours to river cruises that focus on the city’s architecture. There’s a huge variety of options and they are all run by enthusiastic local volunteers who are well-trained and knowledgeable about the city and its past.
Tours from $13-16 USD.
Whether you’re a history buff, a foodie, or someone just looking to explore one of the best cities in the United States, Boston will have a walking tour to suit your needs — no matter your budget! While I like Take Walks the best, any tour company here will be great!
Book Your Trip to Boston: Logistical Tips and Tricks
Book Your Flight
Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.
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 everyone)
- 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 my robust destination guide to Boston for even more planning tips!
