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guided tours guild
From Heritage to Legacy

Get your tickets in advance and discover the human lives of  characters who left their footprints behind for us to follow.

Book An Adventure!
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We Are One

Welcome to Guided Tours Guild, where Captain Pickles brings Boston’s history to life! Our immersive tours uncover the untold stories of the city’s past — tales of grit, glory, and the everyday folks who built America. With lively storytelling, we dive into the events and characters that shaped the nation, sparking a renewed sense of pride and connection to our shared heritage.

Join Captain Pickles to explore Boston’s streets, relive its revolutionary spirit, and carry forward the legacy of those who paved the way.


Book your tour today and step into history!

 

Book A Tour!

Discover Boston’s Story with Captain Pickles

Step into Boston’s past with Captain Pickles, your guide to the city’s most thrilling historical adventures!

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More Than Just a Tour

Guided Tours Guild (GTG), led by the spirited Captain Pickles, isn’t your average tour company—it’s a journey into the heart of Boston’s past. We bring history to life with vivid storytelling, uncovering the tales of real people—revolutionaries, workers, and unsung heroes—who shaped America. Our mission is to make history exciting, relatable, and unforgettable, connecting you to the spirit of the city and the nation.
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Bringing History to Life

Captain Pickles’ immersive tours dive deep into Boston’s streets, revealing the grit and glory behind the city’s biggest moments. Through captivating stories, we spotlight the characters who built this nation, from bold rebels to everyday folks. Every step is a chance to relive the past and feel its pulse in the present.
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Join the Adventure

Our tours do more than share facts—they spark a connection to America’s legacy. With Captain Pickles as your guide, you’ll walk away with a renewed sense of pride and a story to carry forward. Come explore Boston’s history, feel its revolutionary fire, and discover why the past still matters.

What Adventurers Say About Captain Pickles’ Tours

Hear from those who’ve walked Boston’s historic streets with Captain Pickles! Our guests share how Guided Tours Guild brought the city’s past to life with unforgettable stories and lively adventures.
"This was wonderfully fun and informative - Captain Pickles did an amazing job - he totally knows history truly seems to enjoy what he is doing - he is very knowledgeable and funny! He made the tour worthwhile. I have friends here from Manchester England and they wanted to see "history" I was born and raised in CT and it refreshed my lessons! I recommend doing this tour and request Captain Pickles!!"
Kristin G
Tourist
"My wife and I expected a basic Freedom Trail Tour, but Captain Pickles made it unforgettable! His passionate storytelling brought history to life, connecting figures and timelines vividly. The 1 hour 45 minute tour wasn’t long enough. We hung on every word and highly recommend Captain Pickles as the ultimate guide!"
Steven Z
Tourist
"Captain Pickles is the GOAT! Initially skeptical of a costumed guide, I was blown away by his knowledge and passion. His Freedom Trail Tour offered a fresh, nuanced perspective, tying past to present. Even after another tour, this felt personal and engaging. Make an exception for Captain Pickles—you won’t be disappointed!"
Cailin L.
Tourist