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Introducing The Freedom Trail History & Photo Tour

Hello! I hope everyone is well this late November evening! I’m here today to share some GOOD news – something we could all use a little more of this year! I have officially resumed my title as tour guide (Fun fact: I’ve led tours in LA & NYC), as an Experience Host for Airbnb! Say hello to Airbnb’s newest experience, my Freedom Trail History & Photo Tour!

Disclaimer: This post was originally written in November 2020 and was updated in January 2022 for relevancy. After a successful year of tours in Boston, I’ve put my experience on pause as I am now pursuing my MBA down in South Carolina! I plan on reopening my tour slots when I’m back in Boston and will update this post when I do. If you’re looking to do a self-guided walking tour of the Freedom Trail, you can use my Freedom Trail post to guide you!

Freedom Trail tour
Freedom Trail tour

How It Started…

It all began this summer when my Dad and I walked the Freedom Trail start to finish for the first time. We’ve lived outside of Boston our entire lives, but had never done the full walk, so we spent a day doing it! It took us about 4 hours to maneuver from the Boston Common to Charlestown, taking several detours and a lunch break along the way. It was such a great way to learn more about the Revolutionary War history in my home city. I realized that there are probably SO many locals, never mind tourists, who’ve never seen the sights on the Freedom Trail. This lit a lightbulb inside my head.

Freedom Trail tour in Boston
Freedom Trail tour in Boston

I discovered Airbnb Experiences while looking for an Airbnb to stay in recently. I was SO impressed by the selection of tours offered by locals in cities all around the world. There are quite a few unique ones in Boston, including a North End Food Tour and private photo shoot session. After learning more, I thought…hey, I could do this!

Disclaimer: I’m an Associate of Airbnb and may earn a small commission if you book a stay through my link at no additional cost to you!

About My Freedom Trail Tour

There are already quite a few Freedom Trail tours on Airbnb’s site, but I noticed that none of them cover more than 1-2 miles of the trail and are very history focused. I wanted to create a tour that combined my love for history with my blogging favs – photography and teaching others about the world! And thus, the Freedom Trail History & Photo Tour was born!

Freedom Trail Tour Boston

My tour is about 3 hours long and covers 3+ miles of the Freedom Trail. We begin at the Boston Common Visitors Center, located at 139 Tremont Street, and walk all the way to Copp’s Hill Burying Ground in the North End. We cover 14/16 stops on the 2.5 mile-long Freedom Trail! The only two stops not included are the USS Constitution and the Bunker Hill Monument in Charlestown because these stops are a bit too far.

Here’s a screenshot of our route that I made on Google Maps:

Freedom Trail History & Photo tour route

Faneuil Hall is our half way stop and the place where my guests are welcome to grab a bite to eat! This is optional of course, as the tour is completely outdoors, but most people like to grab something from Quincy Market. I also scheduled in an optional pastry stop at my personal favorite, Mike’s Pastry, in the North End!

Our Stops

Here’s a list of the stops we will visit in order:

  1. Boston Common
  2. Acorn Street 
  3. Massachusetts State House
  4. Park Street Church
  5. Granary Burying Ground
  6. King’s Chapel & Burying Ground
  7. Boston Latin School & Benjamin Franklin Statue
  8. Old Corner Bookstore
  9. The Old South Meeting House
  10. Old State House
  11. Boston Massacre site
  12. Faneuil Hall
  13. Mike’s Pastry
  14. Paul Revere House
  15. Old North Church
  16. Copp’s Hill Burying Ground
Walking the Freedom Trail in Boston, MA

I provide historical background at each stop, along with Boston fun facts as we walk. The photo portion of this tour comes into play on Acorn Street, where I’ll take the perfect photo for your gram or FB page, and throughout the tour as I point out some of the most picturesque views in the city. I promise you’ll leave my tour with a new-found understanding of the history of Boston, some fire photos in your camera roll, and a yummy treat in your hand!

Freedom Trail tour in Boston

Signing Up!

If you’re interested in signing up, you can join a tour at the link below. I have availability most days of the week on either a 10:00 – 1:00 pm tour or a 1:30 – 4:30 pm tour.

Whether you’re just visiting the city or have been a local to Boston your whole life, I hope you consider signing up! I promise you’ll learn a lot!

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Freedom Trail tour guide

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