Politically Incorrect Food Tour in Boston

Imagine exploring the bustling, historic streets of Boston’s North End, uncovering hidden gems, and indulging in some of the most delicious Italian cuisine the city has to offer. That’s exactly what awaits you on the one-of-a-kind Politically Incorrect Food Tour Boston. If you’re tired of the same old guided tours, this unconventional food tour will leave you with a fresh perspective on Boston’s beloved Italian neighborhood. Join us as we dive into this unique adventure, led by local Italian-American Anthony Gesualdi, and discover what makes this tour so special.

Short Summary

  • Explore Boston’s Little Italy with the Politically Incorrect Food Tour, led by passionate local Anthony Gesualdi!
  • Discover iconic historic landmarks and tantalizing culinary heritage in the North End.
  • Dress comfortably, bring an appetite & keep an open mind for a truly unforgettable experience!

Experience the Unconventional North End Food Tour

The Politically Incorrect Food Tour Boston offers an unparalleled journey through the North End, the city’s “Little Italy.” With a leisurely paced walking tour led by a true local, Anthony Gesualdi, you’ll experience the North End like never before.

From visiting historic landmarks such as the Paul Revere House and Old North Church to wandering through narrow streets and local hangouts, this tour is a perfect blend of history, culture, and mouthwatering Italian cuisine.

Whether you’re a Boston native or a first-time visitor, this tour promises an authentic and unforgettable experience.

The Tour Experience

On your thrilling North End Food Tour, you’ll be treated to a wide variety of authentic Italian cuisine, including homemade pasta, fresh seafood, and traditional Italian desserts. As you stroll through the neighborhood, you’ll also discover historic landmarks such as the Paul Revere House, the oldest house in the city, and the Old North Church, the oldest church in Boston. In addition to these famous sites, you’ll also explore hidden local hangouts like the North End Market and the Italian American Club, where you can rub elbows with locals and experience the vibrant community spirit that makes this neighborhood so special.

While the incredible food and fascinating history are undoubtedly the stars of the show, what truly sets this tour apart is your passionate local guide, Anthony Gesualdi. Born and raised in the North End, Anthony’s in-depth knowledge of the area and its Italian-American heritage will make you feel like you’re uncovering the neighborhood’s secrets with an old friend. His unique storytelling abilities and infectious enthusiasm will keep you entertained and engaged throughout the tour.

Meet Your Guide, Anthony Gesualdi

Anthony Gesualdi is not your average tour guide. A local Italian-American who grew up in the North End, he brings a wealth of knowledge and personal experience to the Politically Incorrect Food Tour. Anthony’s passion for his neighborhood and its rich history is evident from the moment you meet him, as he enthusiastically shares stories of growing up in the area and watching it evolve over the years.

What really sets it apart is what really sets it apart. Anthony apart from other tour guides, however, is his absolutely hilarious and engaging storytelling style. As one satisfied customer who booked the tour for their Italian mother’s birthday present put it, Anthony was “solid gold” and had them laughing from beginning to end. His unique blend of humor, history, and personal anecdotes make the tour an unforgettable experience for both first-time visitors and locals alike.

Discovering Boston’s Pocket-Sized Italian Neighborhood

Boston’s North End is the city’s oldest residential community, settled in the 1630s and known for its Italian-American population and fine Italian restaurants. With over eighty restaurants and countless wine shops, bakeries, and Italian salumerias (a.k.a Italian delis), the North End is a food lover’s paradise.

As you embark on the Politically Incorrect Food Tour, you’ll dive deep into the heart of this pocket-sized Italian neighborhood, uncovering its rich history and vibrant culture. As you explore the narrow streets and hidden alleyways of the North End, you’ll encounter a variety of historic landmarks and local hangouts. From the famous Paul Revere House and Old North Church to lesser-known gems like Copp’s Hill Burying Ground, the tour offers a unique and comprehensive look at the neighborhood’s past and present.

With Anthony’s guidance, you’ll also discover the best places to eat, drink, and shop in the area, ensuring you leave with a true taste of Boston’s Little Italy.

Historic Landmarks

The North End is home to some of Boston’s most iconic historic landmarks, including the Paul Revere House, Old North Church, and Copp’s Hill Burying Ground. Built in 1680, the Paul Revere House is the oldest house in the city and once belonged to the famous patriot himself. As you stand in its shadow, you can’t help but feel a sense of awe at the rich history that surrounds you.

Another must-see site on the tour is the Old North Church, built in 1723 and known as the oldest church in Boston. This historic landmark played a crucial role in the American Revolution, as it was from its steeple that the famous “One if by land, two if by sea” signal was sent.

And finally, don’t miss Copp’s Hill Burying Ground, the city’s oldest cemetery, established in 1659. These historic landmarks paint a vivid picture of the North End’s storied past, adding an extra layer of depth and intrigue to your tour experience.

Exploring Narrow Streets and Local Hangouts

The North End’s maze of narrow streets and alleyways is a treasure trove of hidden gems waiting to be discovered. As you wander through the neighborhood, you’ll come across popular streets like Hanover Street and Salem Street, lined with charming shops, restaurants, and cafes. Whether you’re in search of the perfect cannoli or a cozy spot to enjoy a glass of wine, the North End’s narrow streets offer endless possibilities.

In addition to the well-trodden paths, the Politically Incorrect Food Tour also takes you off the beaten track to uncover local hangouts and hidden gems. From friendly neighborhood bars to hole-in-the-wall cafes, these spots offer a glimpse into the daily life of North End residents and a chance to experience the area’s vibrant community spirit. With Anthony’s guidance, you’ll feel like a true local as you explore the neighborhood’s hidden corners and secret spots.

Savoring Authentic Italian Cuisine


The North End’s Italian-American community has heavily influenced the area’s culinary scene, creating a mecca for authentic Italian cuisine. From homemade pasta dishes to fresh seafood and traditional Italian desserts, the Politically Incorrect Food Tour offers a mouthwatering array of options for food lovers. As you savor each delicious bite, you’ll gain a deeper appreciation for the flavors and textures that make Italian cuisine so beloved around the world.

And what better way to enjoy this culinary adventure than with the guidance of a passionate local like Anthony? As an Italian-American who grew up in the neighborhood, Anthony has a wealth of knowledge about the area’s best restaurants and hidden culinary gems. From the perfect slice of pizza to the most delectable cannoli, Anthony will ensure that you leave the tour with a full stomach and a newfound appreciation for authentic Italian cuisine.

Countless Wine Shops and Delis

In addition to the amazing restaurants, the North End is also home to a plethora of wine shops, bakeries, and Italian salumerias (a.k.a Italian delis). As you stroll through the neighborhood, you’ll encounter establishments like V Cirace & Son, The Wine Bottega, Hanover Wine & Spirits, and The Wild Duck Wine & Spirits, offering an incredible selection of fine wines and spirits to complement your culinary adventure.

And let’s not forget the Italian delis and bakeries that line the streets of the North End. From the mouthwatering aroma of freshly baked bread to the enticing display of cured meats and cheeses, these family-owned establishments are an essential stop on your food tour.

Whether you’re a seasoned foodie or a casual diner, the North End’s countless wine shops and delis are a testament to the neighborhood’s rich culinary heritage and a true delight for the senses.

A Taste of Home: Italian Mother’s Birthday Present

The Politically Incorrect Food. Tour isn’t just a feast for the senses; it’s also an unforgettable experience that can create lasting memories for those who embark on this culinary adventure. One customer, who booked the tour as an Italian mother’s birthday present, was ecstatic about their decision. They found Anthony’s storytelling absolutely hilarious and praised him for his solid gold humor and engaging personality.

This heartwarming story highlights the truly unique nature of the Politically Incorrect Food Tour. With Anthony’s hilarious storytelling and deep-rooted passion for the North End, the tour offers an experience that is equally entertaining and informative.

Whether you’re celebrating a special occasion or simply looking to explore the neighborhood, the Politically Incorrect Food Tour is sure to leave a lasting impression and a newfound love for Boston’s Little Italy.

Tips for Enjoying Your Politically Incorrect Food Tour

To make the most of your Politically Incorrect Food Tour experience, it’s essential to come prepared. In this section, we’ll share some practical tips that will help you enjoy your tour to the fullest, from dressing comfortably to keeping an open mind.

With these simple yet effective tips, you’ll be ready to embark on your culinary adventure through Boston’s North End with confidence and ease.

Dress Comfortably

One of the most important things to remember when embarking on the Politically Incorrect Food Tour is to dress comfortably. Since the tour involves a significant amount of walking, it’s crucial to wear layered clothing and flat rubber-soled shoes to ensure your comfort throughout the journey.

Additionally, carrying an umbrella is a good idea in case of sudden weather changes. With the right clothing and footwear, you’ll be able to fully enjoy your tour without any discomfort or distractions.

Bring an Appetite

The Politically Incorrect Food Tour is all about savoring authentic Italian cuisine, so be sure to bring a hearty appetite to make the most of your culinary adventure. With an array of delicious dishes to sample, you’ll want to ensure you have enough room to taste everything the tour has to offer.

And don’t forget to bring along some snacks, like granola bars or fruit, to keep your energy levels up between stops.

Keep an Open Mind

Finally, it’s essential to keep an open mind when taking the Politically Incorrect Food Tour. Be prepared to try new foods, ask questions about the ingredients and preparation methods, and embrace the opportunity to learn about the North End’s history and culture.

By maintaining an open mind and being receptive to new experiences, you’ll not only enjoy the tour but also gain a deeper appreciation for the neighborhood and its culinary delights.


The Politically Incorrect Food Tour Boston offers a truly unique and unforgettable experience, combining the rich history and culture of the North End with the mouthwatering flavors of authentic Italian cuisine. Led by the passionate and hilarious local guide Anthony Gesualdi, this unconventional tour will take you on a journey through Boston’s beloved pocket-sized Italian neighborhood, uncovering hidden gems, historic landmarks, and local hangouts along the way.

Whether you’re a first-time visitor or a lifelong resident, the Politically Incorrect Food Tour is an adventure not to be missed. So lace up your comfortable shoes, bring an appetite, and get ready to immerse yourself in the vibrant world of Boston’s Little Italy. Buon appetito!

Michele Thompson
About the author

Born and raised in the midwest, Michele moved to Boston in 1994, armed with nothing but her adventurous spirit and an insatiable appetite for culinary exploration. Over the years, she’s trekked through every neighborhood, from the historic North End to the innovative kitchens of Cambridge, in her quest to discover and taste the city’s offerings. She is a dedicated devourer of everything from mom-and-pop pastries to five-star dining experiences.

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