The Best Boston Walking Tours,
4 Incredible Routes
Interactive walking tours of Boston, bring the city to life.
- CityDays brings an immersive new way to have a walking tour in Boston
- Discover Boston's historic landmarks, secret sights & hidden gems
- Solve fun challenges & puzzling clues to unlock your way
- Optional breaks at top-rated pubs, bars and cafes
- Interactive private tour, you and your team, at your own pace
- Full money back guarantee. We know you'll love it









What to expect on a CityDays Boston walking tour
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- Messages sent to your phones - we'll send your walking tour to any international phone number.
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- Clues, challenges, & puzzles - interact with the city to unravel obscured directions and find your way.
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- The perfect difficulty - just the right amount, inclusive for all, with help available should you need it.
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- Landmarks & hidden gems - see Boston in a new light, a tour showing off quirks too!
Don't have a great time?
Simply let us know why and we'll refund you in full.
Find Your Nearest Boston walking tour
Each game explores a different area of city in one of two ways. Our classic games use puzzle-filled directions to guide players to exciting new sights. Our Story games do all this with the added bonus of an immersive story on top - play the main character and relive a tale from the city's past or experience a story all your own.
Boston walking tours

Finding Freedom
A city's fight for freedom… more

- Coming soon, get notified
The Beacon
The quintessential Boston landscape.… more
change the date, time, number of people or game.

- Coming soon, get notified
Art in the Cradle
Through art comes new life… more
change the date, time, number of people or game.

- Coming soon, get notified
The Founding
Where Massachusetts was born.… more
change the date, time, number of people or game.
How the Boston walking tours work
Clues & Puzzles
Clues don't require any prior knowledge and are made up of two parts:
1) Obscured directions that make reference to the city around you. Unravel their meaning and be guided by your surroundings.
2) A puzzle to be solved once you've followed the directions, search nearby to find your answers.
CityDays aim for an enjoyable, just-the-right-amount, level of difficulty that is inclusive for all! Help messages are available should you need a bit of support.

Guided by clues sent to your phone
- Receive snippets of history, quirky facts and intriguing stories about the areas you visit.
- Pub/cafe breaks along your hunt, all totally optional and some with discounts on food & drinks.
- Make memories at locations along the way, get inspiration from previous teams and share a clever snap!
- Go at your own speed, or go for top spot on the game leaderboard.

Boston walking tour Reviews
The great things you say about CityDays Boston walking tours

Brexit with Benefits
We had a great day, exploring parts of London we’d never seen before and trying to figure out clues. Good that all clue…

Slytherin
This was a great trail with clues that were hard but not impossible! It takes you around some of the lesser known beaut…

Squad11
Great fun was had by all. Perfect way to celebrate our son's birthday being out and about. Would love to do again!

Westies
Excellent day out seeing so many of London’s hidden gems. Brilliantly organised, exhausting fun!

Double-Decker Dashers
Great day out to see Londonderry hidden gems

Lost in transit
Had an awesome time! We found it a great level of challenge and stumbled across many hidden gems that we would never h…

Ronos Ramblers
Fantastic day- lovely birthday treat.

Purple Moustache
We thought this was really fantastic. We all know London but it took us places we had never been and it showed us Lond…

The Kempos
Great experience which we all enjoyed (adults & kids). Can take as much time as you need with the scheduled breaks. Hel…

Team Premier Lodge
Such a great day!! Highly recommend the experience

In it for Fun
Brilliant day out. Loved every minute of it. Saw places we haven't seen before. Clues great. The breaks ans stopping pl…

Sisters go the distance
Great experience! Great clues! Great day!As Londoners we thought we would find it easier but saw so many new places.

Dusty Moquettes
Great fun; enjoyable exploration even for seasoned Londoners

4WAGS-Bicester
Brilliant…. Fantastic experience with friends, hope to do one somewhere else!!!

Double A
Really good fun, saw bits of London you usually wouldn't with a competitive edge to it!

Team Vaughan
Really good fun. Some of it you really had to think about! Especially at the end, but what a great concept. Loved it!

You'll like us by Episode 4
Lots of fun! Set in a great location to explore parts of historic East London. Well thought out and fun games mixed wel…

Not Fast Just Furious
Such a fun day out, worked so well and a lovely way to see parts of London I hadn’t seen despite living here all my lif…

Mums & Sons
Loved doing the race across London.had so much and saw bits of London we’d never seen. A few clues were a bit tricky es…

The Flint's
Great afternoon spent with my son racing across London. We had a fab time exploring parts of London we had never seen b…
Ready to see lots of smiling faces? Read all our customer reviews
Ready? Book your Boston walking tour today
Get The Most Out of Your Boston Walking Tours with CityDays

Discover more of Boston with CityDays!
Our Boston walking tours are designed to take you above and beyond your typical sightseeing experience. We’re dedicated to showing you the places you’d expect to see, but we slip in a bunch of cool hidden stuff along the way too. And the best part? You have to seek them out yourselves!
By interacting with and learning about Boston’s streets, landmarks, history and famous figures, you’ll navigate your own way around Boston by answering puzzles, riddles and clues based on your surroundings.
Our self-guided walking tours in Boston transform you into detectives, explorers and tour guides, giving you the freedom to discover the city your own way, in your own time, with people you know and love.
From the moment you start until you finish the tour, you’re guaranteed to learn, have fun, make memories and get some fresh air and exercise.
The Best Walking Tours in Boston

No lines, no waiting around, no hassle.
That’s part of what makes CityDays’ Boston walking tours the best in the city.
We’ve created a model that allows you to take charge of your Boston walking tour. This ensures that you can walk at your own pace, take breaks whenever it’s convenient for you, and tour with whoever you want! Here’s how it works.
Since we don’t physically attend your tour with you, you don’t even have to listen to our stories or facts (but you can - and should - read all about them in your own time!).
Remember though - just because we’re not there, it doesn’t mean we aren’t paying attention. We check our leaderboards and reward winners for having a great time on our Boston walking tours and we’re only a text away if you need additional help.
Boston History Walking Tours: Uncover Boston’s Inner Sanctum

From a 7th-century English priest who gave Boston its name to a rector-turned-songwriter who penned a famous Christmas carol, Boston has seen its fair share of history.
Our self-guided walking tours in Boston celebrate all the city’s cultural quirks and mysterious facts .
In fact, we’re so fanatical about the Massachusetts capital that we’ve spent hours digging up cool quirks and interesting stories to share with you - here’s a sneak peek at what you can expect from our Boston walking tours (self-guided).
A Modern Aesop's Fable Exists in The City
Bostonians are probably familiar with the “The Tortoise and The Hare” sculpture in Copley Square, but you might not know that the sculpture - or rather the sculptor - indirectly led to the building of Boston’s skate park.
The sculptor’s name is Nancy Schön, and in 1995, she was distressed to learn that “The Tortoise and The Hare” sculpture was being used by bored / skate-happy teens as skate ramps. Schön visited the sculpture to talk to the kids who told her they had nowhere else to skate.
Emboldened, Schön spent 20 years campaigning for a skatepark for the city’s skaters to have somewhere to go. The park was supported by legendary skateboarder Tony Hawk, who donated 9 million dollars to the cause. In 2014, Schön’s wish was finally granted when the skatepark opened. The only trace of Schön you’ll find at the skatepark are some well-hidden engravings of a tortoise and a hare on the floor to commemorate her hard work.
Boston’s Chinatown Used to Be Called “Little Syria”

From the 1880s until the 1930s, Boston and Massachusetts was home to one of the largest Syrian and Lebanese diasporas in the U.S.
The immigrants from Syria and Lebanon were primarily of Christian faith and it’s estimated that by the 1930s, there were 40,000 Syrians living in the state of Massachusetts.
Boston is Named After The Patron Saint of Boundaries, Trade and Travel
Most Bostonians know that the city’s name came from a town many miles away in England, but a few may not know that the other, less famous Boston was named after a Saxon Christian Saint by the name of Botolph.
Believed to have been born in the 7th century, Botolph was later venerated by the Catholic church as the Patron Saint of boundaries, trade and travel - a perfect candidate for Boston in Massachusetts where these three things played a pivotal role in the United States’ independence!
Streets in The Back Bay Are Named Alphabetically
If you look up and see signs for Arlington, Berkeley and Clarendon Streets and wonder if you’re losing your mind, don’t worry - all’s well.
Back in the 1800s, when Boston was undergoing rapid growth and being laid out according to a grid pattern, the streets were named after English Earldoms (the titles of English Lords).
The alphabetical names start from “Arlington” and stretch through to “Hereford”.

Available Trails and Boston Walking Tours
Interested in finding out more about the kinds of self-guided walking tours in Boston we provide? Here’s where you get a tiny sneak peek into where you can find your next adventure…

Finding Freedom
Embark on “Finding Freedom”, a riddle-filled walking tour through Boston’s historic center that blends city exploration with the compelling story of America’s journey to freedom.
Trace clues around key landmarks and hidden treasures, delivering into their significant roles in the nation’s quest for liberty. Along the way, you’ll meet figures such as founding fathers, champions of equality, and an infamous British monarch.
This interactive experience weaves entertaining puzzles through Boston’s streets with fascinating (and educational!) information, offering a dynamic way to learn about the city’s past and present.
Discover sites once steeped in unrest and revolution, as well as finding great spots for dining, shopping and more. Highlights include Faneuil Hall, Quincy Market, Old State House, Post Office Square and Old South Meeting House.
The ideal debenture for families, friends or colleagues, Finding Freedom provides a comprehensive exploration of Boston’s rich history and vibrant culture.