The Best Boston Walking Tours

Boston’s rich Jewish heritage is explored on this 2-hour walking tour of the city’s historic synagogues, Jewish monuments and neighbourhoods. Guests will get to learn about the 19th century Jewish roots of areas like Beacon Hill and tour key Jewish gathering sites such as the Vilna Shul. Other notable stopping off points include the Puffer House Cigar-Rolling Factory and Boston’s stirring and heart-rending Holocaust Memorial, a set of glass structures commemorating the events of World War II.

Walk through history along the Boston Freedom Trail’s famous red line to experience some of the most seminal landmarks of America’s revolutionary founding. Walk in the footsteps of the founding fathers, hear the echoes of patriotic orators like Samuel Adams in the precincts of Faneuil Hall, and recall the blood in the snow outside the Old State House on the night of the Boston Massacre. Eleven of the sixteen official Freedom Trail historic sites are featured during this 90-minute tour, which covers a distance of around 1 mile.

Discover the world of the Boston Brahmins on this small group walking tour of Beacon Hill and the centre of Boston. From sights such as the memorial to the Irish Famine and the city’s most prestigious membership library, infused with Italian sculptures, French maps and testimonials of the Brahmin’s love affair with the Grand European Tour, you’ll learn about the class that helped shaped Boston and set the wheels in motion for the rest of America. Groups are kept to a maximum of 6 people to allow for a personalized service and for your historian guide to answer any questions.

This three-hour Italian-themed walking tour offers a great way to delve under the skin of America’s oldest neighbourhood and learn about its culinary methods, tastes and traditions. You’ll come away with insider cooking tips, as well as advice on where to buy the very best ingredients. Stopping off at various specialty food shops, you’ll get to sample everything from Italian prosciutto, cheese, olive oil and balsamic vinegar through to seasonal fruit and vegetables, as well as classic Italian dolce. You’ll also visit an enoteca to learn to select aperitif to begin, wine to compliment and digestive to conclude the meal.

Aimed at photography enthusiasts of every age and standard, this two-hour walking tour invites you to capture pictures of Boston’s most famous (and photogenic) sights and attractions. Run by a professional local photographer, the tour takes in two of the city’s most historic sites on the Freedom Trail followed by Beacon Hill, a 19th-century English-inspired neighbourhood, and numerous other areas too. During the tour your guide will offer creative photography tips and tricks to help ensure you leave with memorable snaps to cherish forever. Guests can bring either a digital SLR or simply take pictures with their smartphone. The standard tour runs on Friday mornings, but private tours are also available on request. A photography e-booklet is included in the price.

At the end of most city walking tours, you may expect to be nursing a ravishing thirst and hunger. Not so with this 3-hour tour of Boston, which invites guests to sample some of the city’s finest pizza while sinking cold beers in eateries and taverns teeming with history. Among them are a pub where the founding fathers are said to have plotted and planned the American Revolution, and another where the infamous Great Brink’s Robbery took place. You’ll also head to Charlestown to see famous sites including the Bunker Hill Monument, the USS Constitution and a tavern that dates back to 1785. The tour ends at either Bell in Hand, the longest continuously operating tavern in the United States, or the Green Dragon, a basement tavern known as the Headquarters of the Revolution.

Stoll along the 18th-century streets and alleys of Boston’s historic North End neighbourhood on this small-group 3-hour walking tour. A knowledgeable guide will take your group, limited to just six people, in tracing the city’s evolution from the American Revolution to the current day. During the tour you’ll walk in the footsteps of pioneers while learning about historic events such as the Boston Tea party and the role of the city’s shipping industry in creating modern day Boston. After the tour, you’ll be perfect placed to grab a bite to eat in one of the district’s famous Italian eateries.

Not one for the faint-hearted, this spooky tour offers guests the chance to unearth some of Boston’s darkest secrets aboard the Trolley of the Doomed, a 17th-century grave digger which roams around the haunted streets and burial grounds of Boston. You’ll walk through two of the city’s oldest burial grounds, visit the site of the biggest grave-robbing scandal in New England’s history, and hear the stories of those lost souls who many locals believe still wander the streets and alleys of this historic town.

Visit premium wine destinations in Boston’s historic North End neighbourhood on this 2-hour wine-tasting walking tour. Home to charming mom-and-pop restaurants and beautiful wine shops selling a superb range of locally produced wines, the North End boasts excellent wine-tasting venues that you’ll discover in the company of a knowledgeable, experienced and friendly tour guide. This small-group tour is limited to a maximum of 12 people to provide an intimate experience with fellow wine enthusiasts.

This 2-hour takes guests on a fascinating tour through the historic streets of North End, Boston’s oldest district, stopping off at numerous important landmarks along the way. You’ll get a taste of Revolutionary New England as you visit key sites along the Freedom trail, before immersing yourself in the colourful neighbourhood which boasts a rich Italian American heritage. To complete the tour, you’ll be chaperoned to Boston’s waterfront and harbour where you can catch a glimpse of the USS Constitution, a wooden-hulled heavy frigate named by President George Washington after the Constitution of the United States of America.