Boston Food and History Highlights of the Freedom Trail Private Tour

  • 5 Hours
  • Walking Tour
  • Max Guests: 12Groups 13+ Please call to book
  • Private Tour
  • Daily


  • Enjoy the combination of Boston’s history and delicious food on this fabulous walking tour.
  • Savor a bite from a traditional Italian bakery, pizzeria, or cafe as you stroll through the North End neighborhood.
  • Experience life as the locals do as you are swept up into the hustle and bustle of a historic market.
  • Wander through the beautiful historic buildings and skyscrapers while learning about Boston’s famous figures such as Sam Adams and Paul Revere.
  • Imagine a time gone by as you meander through the picturesque landscaping of the Boston Public Garden.

History and food are both great, but combining them takes it to another level. See for yourself on our Food and Freedom Trail Tour, which leads you on a fascinating, entertaining, and delicious stroll through Beantown.

Immerse yourself in the rich foodie culture of the North End and Boston’s markets before winding your way down the historic Boston Freedom Trail (as well as some off-trail spots that locals love). Along the way, enjoy a variety of local (and yummy!) food samples while your expert guide shows you their favorite local locales and gives you the inside scoop on Boston’s incredible past.

It’s the best of Boston, all in one day!

Community Impact

We mindfully design our tours to explore areas on foot, thus doing our part to lessen our environmental impact.

Our guides prioritize “supporting local” by recommending and patronizing family-run and locally owned businesses so that the culture and traditions of this neighborhood are preserved and are passed on to the next generation.

We are committed to a 360-degree view of storytelling, featuring stories about under-represented groups such as women, immigrants, and people of various ethnicities, ages, and religions.

Your guide will point out the importance of preserving architecture in a booming city where instead of tearing down historic buildings, we have restored and created a city around them.

We will explore various neighborhoods in which immigrant and under-recognized populations, sometimes welcomed and sometimes not-so-welcomed, have left permanent and positive impacts on the history and culture of our modern city.


The Greenway Carousel

Your tour begins at the Greenway Carousel , the only carousel of its kind. The hand-carved characters are inspired by the air, sea and land animals of Boston Harbor, and by the imaginations of children.

Faneuil Hall and Faneuil Hall Marketplace

Your first stop on the foodie half of your tour is at Faneuil Hall and its Marketplace. This destination is a lively market and town hall and is located close to the waterfront. This is where the cries for revolution from Great Britain first rang out.

Rose Kennedy Greenway

Your tour will pass this picturesque park and you’ll see the unique memorials, fountains, parks, and art exhibits that reside here, along with skyline views. This will be where your tour eventually concludes.

North End

Your guide will introduce you to the vast choice of different drinks and bites and you’ll get to experience them yourself! From breads to cheeses to pizza, it’s got it all – so arrive hungry! As you’re munching, our guide will teach you all about the history of the North End – one of Boston’s most iconic and popular neighborhoods.

Paul Revere Mall

Enjoy a stroll down this tree-lined promenade and snap a picture of the man himself atop his horse, as your guide tells the immortalized tale of Paul and his Midnight Ride.

Old North Church

Along the tour, you’ll get a view and maybe an inside look of the steeple of the Old North Church (one of Boston’s Must See spots). it’s where lanterns were hung on the eve of the American Revolution.

Old State House

Moving into the heart of Downtown Boston, we stop in front of the Old State House and site of the Boston Massacre. The Old State House is one of the most iconic buildings in Boston – a Must See – and is also one of the oldest public buildings in the country. Our guide will educate you on its rich history and why it is so important today.

Old City Hall

This hall was home to the city council in the 19th and 20th century, as well as the site of the first public school in America. You’ll also marvel at its breathtaking French architecture and be able to snap a photo with the famed Bronze Donkey.

Massachusetts State House

You’ll love seeing the glittering dome of the inspiring, historic, and beautiful Massachusetts State House, designed and built by famous federalist architect Charles Bulfinch in 1798. From the outside, take in the views of modern Boston, including the skyscrapers of Downtown, the Financial District, and the tallest building in New England: The John Hancock Tower.

Boston Public Garden

This garden is full of life with residents of Boston enjoying it for walks, exercise, fun, or just a peaceful moment. Your tour will end here – in the perfect central location for you to continue your day in Boston.

Price Includes

Price Excludes

  • Local English-speaking guide
  • A special Boston treat, and a variety of food samples (such as fresh-baked bread, a delicious pastry, beverages, a sample of pizza, or a delectable meat & cheese snack). Food options and portion sizes vary – total amount of food equals a full meal
  • Admission into The Old North Church
  • Additional food and drink, souvenirs, tips/gratuities for your guide.

Pickup Information

Available: Daily

Start times: 10am, 1pm

Meeting Location: 191 Atlantic Ave., Boston, MA 02111 -The Greenway Carousel (Outside – Next to the carousel entrance)


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