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The Best Boston Walking Tours,
4 Incredible Routes

  • 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
Talk to us about team building options

What to expect on a CityDays Boston walking tour

Messages sent to your phones - we'll send your walking tour to any international phone number.
Clues, challenges, & puzzles - interact with the city to unravel obscured directions and find your way.
The perfect difficulty - just the right amount, inclusive for all, with help available should you need it.
Landmarks & hidden gems - see Boston in a new light, a tour showing off quirks too!
Full money back guarantee

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.

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Rated 5/5 on Google
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Rated 5/5 on TripAdvisor

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.

A mix of clues, puzzles and photo challenges

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.
Learn snippets of history, optional breaks in pubs/cafes and a leaderboard for each game.

Boston walking tour Reviews

The great things our customers have to say about CityDays Boston walking tours

Carolines over 50's Club Boston walking tour

Carolines over 50's Club

Fantastic trail , really enjoyed 10/10

Golden Pineapple Boston walking tour

Golden Pineapple

Amazing experience. Great ways to show little nooks and crannies you would otherwise miss. Really fun clues. Would full…

MAD MAX Boston walking tour

MAD MAX

Beautiful experience, group absolutely loved it. Great history and storyline, only thing is that there could’ve been mo…

Candler Clan Boston walking tour

Candler Clan

Had a fantastic day out! We loved the clues and they were the right level of difficulty for the whole family - age 11+.

The Ginger & the Gay Boston walking tour

The Ginger & the Gay

David and I had the BEST day exploring York, solving the clues, and had such a wonderful time over the whole day. What…

Mumson Boston walking tour

Mumson

Had a great day out in London doing the outdoor escape room, I have been round London hundreds of times but found areas…

Shell and Phil Boston walking tour

Shell and Phil

Brilliant clues and a great way to see the city. We will be looking to see which other cities we can do this in!

The Gunners Boston walking tour

The Gunners

We had a great few hours following the clues and exploring a part of London. Definitely tested the brain cells! Loved i…

Brains and Whiston Boston walking tour

Brains and Whiston

Was a intresting and fun filled day 😁. FromBrains & whiston

Special six Boston walking tour

Special six

A fantastic day out finding new places and spotting things you would normally just walk by! Highly recommend this activ…

Rocky Boston walking tour

Rocky

Great for getting out and seeing parts of the city you wouldn't other wise see. Plenty of places for food and drink on …

Wiggins and Simpsons Boston walking tour

Wiggins and Simpsons

Such a great time. We had an amazing afternoon, and enjoyed all the stops along the way!!

Priceless Boston walking tour

Priceless

Great way to explore London. Even if you live here you will discover hidden gems and lots of fun facts

Rescue Aid Society Boston walking tour

Rescue Aid Society

Fantastic day out! Wet and windy, but helped us see a city we are familiar with in a whole different light! Great fun!

Kanye Quest Boston walking tour

Kanye Quest

Very fun to see some areas where we've never been! Good riddles, not too hard but not too easy.

Team PP Boston walking tour

Team PP

It was fantastic! Really interesting clues and made me see my home town in a new way - looking for our next one!

BBSS Boston walking tour

BBSS

It was really excellent experience. We saw lots of places we had never seen and enjoyed the challenge of the clues. We …

A and L Boston walking tour

A and L

We loved the tour! Made us think, tired us out and was great fun! Thank you

Callaghans Boston walking tour

Callaghans

What an excellent way to explore Bath. We had great fun following the clues and finding all about the city. Brilliant w…

SBM Boston walking tour

SBM

Was a fantastic day out! Cannot fault it. Got us thinking, was the right level of challenge, and took us to some beauti…

Read all our customer reviews

Ready? Book your Boston walking tour today

Get The Most Out of Your Boston Walking Tours with CityDays

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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

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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

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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”

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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”. 

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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…

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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. 

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