Top Boston How to Get Around in 2026

Boston’s North End boasts cobbled streets, historical buildings and trendy Italian-inspired food spots—the latter testifying to its nickname of “Little Italy”. Skip hours of Googling and book a private walking tour with a guide who’ll introduce you to the area’s tucked-away gems and tastiest Italian eats. Delve into back alleys, hear tales of local history, find hidden crime and movie locations you'd otherwise miss, and pause along the way to savor treats such as pasta dishes, cannoli and more.

Cruise Boston Harbor aboard a luxury yacht, complete with superb city views and a buffet brunch featuring both breakfast and lunch offerings. For 2-hours you'll explore the waters from Rowes Wharf to the Charlestown Naval Yard and back, sailing past sights such as Castle Island and Boston Light. Spend some time enjoying the yacht's three climate-controlled decks or dancing to the sounds of a live DJ mix.

Maximize time in Boston with this private sightseeing tour focused on city history. Meet your guide in the morning and set out on a city stroll that includes top historic landmarks including Boston Common, Paul Revere’s House, and Faneuil Hall Marketplace. Learn about American history along the Freedom Trail and taste some of Boston’s best food during this full-day private tour.

Explore the cobblestone streets of Boston’s North End and taste your way through the neighborhood with this private food tour. Meet your guide for a half-day tour that includes some of the city’s best Italian food and go off-the-beaten-path to see where locals shop for quality ingredients. Learn about the neighborhood from a local guide while sampling its many flavors.

Taste your way through Boston with a private food-focused tour. Meet your guide for a half-day city stroll that includes popular landmarks such as Boston Common, the Paul Revere House, and the Bunker Hill Monument. Sample several traditional flavors of Boston including Boston clam chowder and Boston cream pie. Learn about local history and culture from your private guide.

Let a costumed colonial dressed expert Guide show you Samuel Adams Boston, Sam Adams was a key figure in many of Boston's key Revolutionary events The Boston Massacre, The Boston Tea Party and more... At The Tour of The Freedom Trail, our Mission is to provide family-friendly experiences that guide guests as they discover Boston's history on walking tours to the historic locations along Boston's Freedom Trail. Join us on a 1 hour and 45 minute walking tour and learn about the inspiring history of Boston on The Tour of The Freedom Trail. Traverse through the graveyards and sites of the Boston's history including the Tea Party and The Boston Massacre with a costumed historical interpreter.

Explore Boston after dark on a guided walking tour focused on true crime, urban legends, and lesser-known historical events. Led by a local guide, the experience emphasizes storytelling and discussion rather than scripted narration. The small-group format creates an engaging evening experience that presents a different perspective on the city’s past beyond standard daytime tours.

There are lots of ways to follow in the footsteps of the founding fathers in Boston, but not many tours allow you to do so while drinking in historic pubs and taverns. On this small-group combination pub crawl and walking tour, visit a range of New England drinking establishments while listening to facts about the country’s formation.

Traverse Boston and learn all about the city’s history while you sightsee on this group walking tour led by a father and son duo. See the Old North Church, the Paul Revere House, Old City Hall, and more, without worrying about getting lost or missing out on hearing the stories behind the sights. An expert guide leads the tour to bring Boston's history to life.

There’s tons of options for things to do in this city, and tons of Tour Guides…while you’re here, come hang out with the most colorful one in town, on the Pizza, Beer, and Paul Revere Tour! I’m Jimbo the Tye Dyed Tour Guide, and I strive to have these tours feel like you’re just hanging out with an old friend, in a new city... grabbing a bite and a beer while checking out some history. Super casual, not overwhelming with dates and facts…just enjoying a couple slices and a beer in a pre-revolutionary Boston. See tiny back alleys ways from the 1700's as we walk down cobblestones the forefathers walked on, on our way to grab two slices of the best pizza you've ever had!! Also, i take a really neat little video of our tour, which i post to my social media pages like instagrem, feel free to find me there and see past videos of people having a wicked good time under: TyeDyedTourGuide!!

Spend a full day exploring Manhattan from Boston with ease on this group tour. Depart early from Boston in a comfortable vehicle with a driver-guide and make your way down to New York City. Take time to visit One World Trade Center, the Statue of Liberty, and Times Square before returning to Boston.

Get to know about Boston’s haunted past and explore at your own pace on this self-guided walking tour. Use the app on your phone and your headphones to learn about Boston’s historical ghost stories and visit a variety of sites whenever you choose to go. Spend more time at places that are interesting for you.

Discover Boston's oldest neighborhood on a food tour that's equal parts delicious and "mostly" accurate. Join a local guide as you wander the cobblestone streets of the historic North End, stopping at handpicked restaurants to sample iconic local favorites. Along the way, you'll uncover fascinating stories, colorful legends, and the rich history that shaped one of America's oldest cities. Perfect for food lovers, history buffs, and curious travelers, this relaxed walking tour combines incredible local flavors with unforgettable storytelling for an experience that's as entertaining as it is delicious. Tour Highlights * Enjoy six generous tastings, including handmade ravioli, brick-oven pizza, a classic Italian sandwich, seasonal New England treats, fresh cannoli, and a Boston lobster roll. * Explore Boston's oldest neighborhood with a local guide. * Discover fascinating history, local legends, and Mostly Accurate stories. * All food and 20% gratuity for each stop is included.

Explore Boston’s musical history while guided by a local musician on this small-group tour, discovering facts about the city’s past and present music scene that most guidebooks miss. Visit several of Boston’s most influential venues and hear about the legendary artists who have played some of their largest gigs in the city.

Discover Boston's pivotal role in the fight for women's suffrage on a guided walking tour through the Back Bay neighborhood. Explore iconic landmarks like Boston Common, the Public Garden, Newbury Street, and Copley Square while delving into the transformative years of 1870 to 1920. Led by local guides, this small-group experience offers insights into the activists and events that shaped women's rights history.

This small-group tour stands out by offering an intimate, authentic experience, allowing guests to connect more deeply with Boston’s local stories. With a focus on personal attention, our passionate local guides share not just historical facts but real, untold stories of the city, making each stop feel unique. The small group size ensures a more personalized experience, giving you the chance to ask questions, interact, and truly immerse yourself in the heart of Boston’s history. It’s more than just a tour—it’s a genuine journey through the city’s past, told by the people who live it.

See Boston's history come alive on a 5-part augmented reality tour along the full Freedom Trail. Walk with a guide as you relive key moments from 1765 to 1775, including meeting Paul Revere and operating a revolutionary war field cannon. These interactive AR experiences use headsets and tablets, bringing historical figures and events into the real world

Experience the charms of Cambridge on this bicycle tour. Sometimes referred to as “Boston’s Left Bank,” Cambridge is a celebrated hub for academia, technology, and culture. Ride across the gleaming waters of the Charles River and visit Harvard Square, MIT, the Stata Center designed by Frank Gehry, and more. Over the course of 2.5 to 3 hours, you’ll cover 11-13 miles in this bike-friendly area.

Ready to mix spirits with… well, spirits? Join Boston’s premier haunted pub crawl, where the drinks are strong and the ghost stories are even stronger. Grab your bravest drinking buddies and stumble (responsibly!) through Beantown’s booziest and most bone-chilling history—from haunted pubs and ghost-filled restaurants to the eerie cemeteries where Boston’s past refuses to stay buried. You’ll hear tales of restless Founding Fathers, scandalous secrets, and blood-stained streets that might just send a chill up your spine—or maybe that’s just the whiskey. So pour yourself a Boston Lager, toast to the dearly departed, and see just how much haunted history you can handle. With Ghost City Tours, it’s all fun and fright until someone sees a ghost... and then it’s even better. *Entry into establishments is subject to operating hours and availability. Drinks not included. Only for guests ages 21+.

Discover Boston’s famed Freedom Trail on a private walking tour through the city. Follow your dedicated guide past key landmarks including Paul Revere’s house, Old North Church, Boston Common, Faneuil Hall, and much more, customizing the tour to your group’s interests. While you walk, your guide regales you with information about Boston’s history with particular emphasis on the American Revolution and independence.

Explore the eerie side of Boston as you take a stroll through some of its most haunted locations with a local guide. Learn about Boston's rich history and the ghosts who inhabit its hallowed halls. Perfect for history buffs and thrill-seekers alike, this 1.5 mile, 90 minute walking tour offers a unique glimpse into the city's haunted past...and present. This is a small group tour, limited to 15 guests, so you are part of a conversation, not a lecture. - Visit some of Boston's most historic and haunted sites - Hear chilling tales of ghosts and supernatural events - Ideal for history lovers and those seeking a thrilling experience - Expert local guide provides insights into Boston's haunted history

New York City is a huge city, so it can be hard to know where to start exploring alone. Instead, get the help of a guide who knows the Big Apple’s secrets on this group guided day tour from Boston or New York City. Spend the whole day getting a well-rounded picture of New York, with the option to include a cruise to the Statue of Liberty or entry to the One World Trade Center Observatory.

Discover the Concord of writers including Thoreau, Emerson, Hawthorne, and Alcott on a private tour focused on literary history. From Louisa May Alcott’s Orchard House to Walden Pond, you’ll find the real-world places behind stories you love. Offering the option to meet your guide in Concord or at a central location in Boston, this tour can adapt to your schedule and preferences, without the fixed itinerary of a group excursion.

See Boston’s historic sites without worrying about inclement weather on this private van tour. Depart from your Boston accommodation in a heated van with a driver-guide and head into the historic center of the city. Visit the Paul Revere House, the Bunker Hill Battle Monument, Fenway Park, and more, and hear stories about each place.