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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

RuddRobins Boston walking tour

RuddRobins

Wonderful way to explore, Nottingham next!

Mayo for Sam Boston walking tour

Mayo for Sam

Great afternoon of puzzles and fun.Everyone enjoyed and even those of us who know London still discovered new things & …

You got snacks? Boston walking tour

You got snacks?

This is the second one of these we have done, we love them. Great day out and takes you places you've not been before. …

Bubbles Boston walking tour

Bubbles

We had a great time. Got stuck on one clue when it said look right not left, but worked it out in the end. We took a fe…

Definitely Maybe Boston walking tour

Definitely Maybe

Excellent experience. Really quick messaging and challenging but fun clues

Dally101 Boston walking tour

Dally101

Myself and my partner really enjoyed this activity. I'm from Scotland and he is from outer London and both found it a g…

Team London birthdays Boston walking tour

Team London birthdays

We had a really great time! Really made my birthday!

TJT Boston walking tour

TJT

Such a unique and fun experience! It really allows you to see parts of the city that you wouldn’t necessarily visit! In…

Ru and Coel Boston walking tour

Ru and Coel

It was amazing getting to tour all the little details of Sydney while having an underlying story and puzzles to solve! …

Princess Squeak & the Silly Goose Boston walking tour

Princess Squeak & the Silly Goose

Such good fun, clever clues, and the trail took us to see parts of York we have never seen before! Loved it!

The Band on Tour Boston walking tour

The Band on Tour

A really fun day out. Got to see lots of the city and learn some interesting facts too!

Blakemores on Tour Boston walking tour

Blakemores on Tour

Excellent way to see the city

Joe’s adventure squad Boston walking tour

Joe’s adventure squad

A great way to explore Greenwich, we all really enjoyed it! Fun and challenging clues to keep us guessing, highly recom…

PRAA Boston walking tour

PRAA

great way to explore the city we have just moved to!

Team Hammond Boston walking tour

Team Hammond

We had a great experience! Cambridge is our local City, but we were amazed at how much we'd never seen within such a sm…

The RamSchals Boston walking tour

The RamSchals

Great day out with kids (age 10-12). We loved it!

Woolpack Meadows explores Boston walking tour

Woolpack Meadows explores

What a fantastic opportunity to have fun and explore York. Thoroughly enjoyed it. Thank you

Toiyub + Amber Boston walking tour

Toiyub + Amber

Amazing experience, it’s something different to do and you get to explore the history of Manchester. I would highly rec…

GOLD Boston walking tour

GOLD

Excellent way to discover parts of London we did t know existed even as a Londoner and fun with friends

Stweam Boston walking tour

Stweam

We had an absolutely fabulous afternoon working out the clues and searching high and low for the answers!! We'll defini…

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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