This Total Boston tour combines three of our most popular group tours — North End Food Tour, From Food to Freedom Trail and Bowling, Bites & A Boat Ride — to give you one perfect day out! 

Your Boston adventure begins at the lifeblood of Boston, the Boston Harbor. We’ll make our way to the heart of the North End, with views of some of the most historic sites and properties in the neighborhood, some dating back to the late 1600s and 1700s. 

Tasty food is never far away in the North End. Your guide will introduce you to a small, hidden Italian bakery serving up fresh bread daily. A proper Italian salumeria is next, where you’ll have a chance to enjoy Italian meats and cheeses at their finest and freshest. 

Take in the energy of the North End’s busiest corridor, Hanover Street, as you take time for a break with your guide at a traditional Italian cafe Here, you will have a chance to enjoy your choice of a classic cappuccino, espresso, or tea. 

Next up, we will make our way to the Old North Church and step inside its hallowed walls. After Church, we’ll dive deeper into the local side of the North End, where a taste of pizza awaits at a neighborhood favorite. We cap off the North End food experience with samples of the best Italian pastries located in the backstreets. Hopefully there will be a chance to meet and chat with the best bakers around if we catch them at a quiet moment. 

Rest your legs for a bit before continuing on with your guide toward the historic Custom House Tower, the city’s first skyscraper.  We’ll take a quick peek inside this picturesque building if we can, then we’ll lead you toward the famous Faneuil Hall and Quincy Market. 

Moving into the heart of Downtown Boston, we’ll stop in front of the Old State House, site of the Boston Massacre. A short trek through Downtown Crossing and past Old City Hall will take you to one of the most historic places in the country, King’s Chapel Burial Ground and King’s Chapel. Whenever possible, your guide will take you inside King’s Chapel, the first church in the USA to have a pipe organ. If we’re lucky, we might just get to hear it being played.    

Somewhere along the way during this tour, you’ll have a chance to rest your legs and enjoy a refreshing local beer. Your guide will choose from among some of the most historic, quirky and hidden local bars and taverns in the area.  

On most weekdays, you’ll have a chance to see the government at work (or not) inside the inspiring, historic and beautiful Massachusetts State House. Outside, you can 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.  

We’ll continue our journey through Beacon Hill, where you’ll have a chance to take in the quintessential architecture of Boston’s red brick row houses. Get out your cameras — this neighborhood is one of the most photogenic in the city. 

We arrive at the beautiful Boston Public Garden, one of Boston’s favorite green spaces, where you’ll see locals walking the dogs, playing with their kids and enjoying lunch in the shade. 

After a short walk or ride back to Long Wharf, you’ll be recharged and ready for an unforgettable time in East Boston. Head underground with your guide to the Blue Line T Station. Your guide will help you navigate the modern system as you get on the train and travel under the harbor through the oldest subway tunnel in the country, which happens to be the third oldest in the world, dating all the way back to 1904. 

We’ll then get off the train and enjoy the local neighborhood scene. As we walk, you’ll see shops and restaurants reflecting the diversity of East Boston’s residents.

Next, it’s time for bowling Boston-style! Before hitting the lanes, you’ll have the option to pick up a beverage to bring over to this classic neighborhood bowling alley, which encourages you to BYOB. With manual scoring, gravity-powered ball return, and wood paneling, this joint hasn’t changed much in 60 years. If bowling isn’t available, we’ll make our way over to our favorite billiard hall where we’ll have a chance to play a game of pool together with the locals.  

The evening continues as you walk down Meridian Street, taking in some murals depicting the history and influence of immigration in East Boston. We will continue to Maverick Square, where we will enjoy a snack or two along the way. You’ll discover the best variety of food in all of Boston concentrated in this area, from Colombian bakeries, to Italian sandwich shops, Mexican taquerias, El Salvadorian cafes and Chinese restaurants. 

Next, we head to the waterfront for stunning views of the skyline and, at certain times of the year, you’ll have a chance to catch an amazing sunset.  

If time allows, and on certain days of the week, we’ll continue walking through the neighborhood and then along the water through a picturesque park and into the Boston Shipyard. Here you’ll see some creative public art, and a chance to visit a local ciderhouse for a tasting. One final bite or two of the amazing East Boston food might also be in the mix. 

Finally, we’ll call the water taxi to bring us back across the harbor. Get your cameras ready for some of the best views of Boston from the water. From the boat, your guide will point out the must-see neighborhoods and landmarks that make Boston special.   Take it all in and enjoy the harbor in style as you cruise back into Long Wharf. 

After an epic day, you’ll probably be ready for bed but before you go, don’t forget to ask your guide for tips on what else to see, do and eat in buzzing Boston!