Brawlers, Smugglers and Redcoats: Boston Self-Guided Walking Tour
Boston’s revolutionary spirit didn’t emerge overnight. It was forged through years of defiance, from merchants smuggling wine, to ropewalkers brawling with British soldiers.
On this walking tour, you’ll find out how everyday acts of resistance transformed colonial Boston into the birthplace of the American revolution. You’ll also uncover the gritty reality behind the propaganda and myths taught in textbooks.
The tour starts at Long Wharf, once the longest in the Western Hemisphere, where 4,000 British troops landed in 1768 to discipline a rebellious city. You’ll walk through the North End, past John Hancock’s counting house where nervous redcoats fumbled musket balls. Along the way, you’ll hear how Hancock beat smuggling charges, and discover why Puritans refused to name their horses.
Duration: 1 hr 30 min – 2 hours
- Free cancellation
- Private tour
Private Shopping Tour from Boston to Kittery Premium Outlets
Comfortable Roundtrip Tour from your hotel in Boston to Kittery Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Boston. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Boston.
All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.
Duration: 6 hours
- Free cancellation
- Private tour
Private Walking Tour in Boston - America's 250th Anniversary
Boston did not just witness the American Revolution. Boston started it. On this private 2-hour walk through the historic heart of the city, you will move through the neighborhoods, markets, halls, and streets where ordinary people made extraordinary decisions that changed the world. From the Rose Kennedy Greenway where modern Boston meets its colonial roots, to Faneuil Hall where civic debate has echoed for centuries, to the gold-domed State House standing watch over Beacon Hill, every stop on this tour is a chapter in America's oldest story. Your private guide, fluent in your language, connects the architecture, the streets, and the people to the nation turning 250 in 2026. The tour ends in the Boston Public Garden, America's first public botanical garden, where you can sit, breathe, and let two hours of history settle in. Boston is where it all began. This is how you experience it properly.
Duration: 2 hours
- Free cancellation
- Private tour
Private Full Day Tour to Coastal Maine from Boston with Hotel pick-up
Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of Maine. Get ready to explore the most beautiful beaches and the nicest spots in this wonderful area.
We will pick you up from your hotel or place of choice (hotel or apartment) in Boston and take you on this private tour, with your own chauffeur and guide to the Coastal Maine.
During your full day private tour you will discover the best spots of the Coastal Maine with your local expert guide. Get ready to explore the Drowned Coast.
This is an example of the itinerary. It will depend on traffic conditions as well as how much time spent in each location.
Duration: 10 hours
- Free cancellation
- Private tour
Private tour to northern Massachusetts coast from Boston - Hotel pick up
Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of northern Massachusets. Get ready to explore the most beautiful beaches and the nicest spots in this wonderful area.
We will pick you up from your hotel or place of choice (hotel or apartment) in Boston and take you on this private tour, with your own chauffeur and guide to the northern coast of Boston.
During your full day private tour you will visit Gloucester and Rockport. You will explore its beautiful rocky coast and sandy beaches. You will of course have free time for lunch along the tour.
Duration: 8 hours
- Free cancellation
- Private tour
An Epic Audio Tour : Boston Revolutionary Trails
"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration!
Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza.
Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll!
With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!
"
Duration: 1 hr 30 min
- Free cancellation
- Private tour
Boston Freedom Trail and Revolution Private Tour
Explore the birthplace of the American Revolution on a private sightseeing ride through Boston’s most historic landmarks. Travel comfortably with your English-speaking Welcome Driver, who will share stories and insights into the events and figures that shaped the United States. Begin at Boston Common, then visit the Massachusetts State House and Granary Burying Ground, where many Revolutionary leaders are buried. Continue to the Old State House, Faneuil Hall, and the Paul Revere House Area, discovering the heart of colonial Boston with time for photos and short walks. End your journey at the Old North Church and Bunker Hill Monument, where pivotal moments of the Revolution unfolded. With private transportation, a flexible itinerary, and local insights, this experience offers a relaxed and memorable introduction to Boston’s revolutionary heritage.
Duration: 5 hours
- Free cancellation
- Private tour
Revolutionary War Boston Lexington and Concord Tour
This private car tour is a special edition Rev War 250 tour.
We've combined a few lesser known, yet hugely significant Revolutionary War sites in Boston, with the main events in the towns of Lexington and Concord in to a half day tour.
Starting in Boston we'll take you to sites where very few tours go and give context to events leading up to the outbreak of the war. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired.
We'll take the same route as Paul Revere, stopping at the most significant sites along the way giving a detailed account of events of April 1775.
The itinerary gives the list of sites we'll visit, timings are flexible and the 4 hour tour time includes travel to and from Concord.
This tour is perfect for those groups who have limited time available in Boston or groups who have different degrees of interest in the history of that time.
Duration: 4 hours
- Likely to sell out
- Free cancellation
- Private tour
Private Revolutionary Heritage Tour from Boston by Car
This private historical tour explores landscapes where American independence began. You travel from Boston into regions shaped by early revolutionary action. In Boston, streets reveal the tensions that led to political transformation. Cambridge introduces academic traditions that influenced national thought. At Harvard Yard, historic buildings reflect centuries of intellectual legacy. Lexington Green presents the quiet field where the first conflict emerged. What moment transformed protest into revolution? At Old North Bridge, you stand where resistance took form. Walden Pond offers a reflective setting linked to classical American literature. Orchard House connects you to literary heritage shaped by cultural identity. Private transport allows a smooth journey through these historic regions. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
Duration: 6 hours
- Private tour
Boston by Night Private Sightseeing Tour
Experience Boston after dark on a private evening sightseeing ride through the city’s illuminated landmarks, historic neighborhoods, and scenic waterfront. Travel comfortably with your English-speaking Welcome Driver, who will share local stories and recommendations along the way. Begin at Boston Common and the Massachusetts State House, then continue through the charming streets of Beacon Hill and Back Bay. Visit Copley Square and the modern Seaport District, where historic architecture meets contemporary waterfront development. End your evening at Fan Pier Viewpoint and the Charlestown Navy Yard Viewpoint, offering stunning skyline and harbor views perfect for photos. With private transportation, a flexible itinerary, and a relaxed pace, this experience is an unforgettable way to discover Boston’s beauty after sunset.
Duration: 3 hours
- Free cancellation
- Private tour
Boston Logan Airport (BOS) to Flynn Cruise Port - Round-Trip Private Transfer
Book your Private Round-Trip Transfer from Boston Logan Intl Airport (BOS) to Flynn Cruiseport Boston and return.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private ,door to door airport transfer.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers
Duration: 40 min
- Free cancellation
- Private tour
Pubs of the Freedom Trail The Crawl to Liberty
Explore Boston’s history with a spirited twist on the Freedom Trail. This lively walking tour blends sharp colonial storytelling with a pub crawl through several of Boston’s most iconic bars. Led by a costumed guide with a talent for good‑natured mischief, you’ll enjoy curated half‑pours of beer or cider at each stop, each chosen to match the landmark and the legend right outside. The tour kicks off at Democracy Brewing and wraps up at either its Beer Garden or The Black Rose, depending on the season. With a two hour run time, it’s a relaxed, rowdy way to raise a glass to Boston’s past.
Visit multiple historic pubs along Boston's Freedom Trail
Enjoy curated half‑pints at every stop
Hear engaging stories tied to nearby landmarks
Costumes aren’t required, but they’re absolutely encouraged (and frequently roasted).
Duration: 2 hours
- Free cancellation
Boston Logan Airport to Killington/Okemo Private Transfer
Book your private Arrival transfer from Boston Logan Int Airport (BOS) to Killington/Okemo Mountain Ski Resort.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers
Duration: 2 hr 50 min
- Free cancellation
- Private tour
Boston America's 250th Road that Made a Revolution Tour
America turns 250 only once. This is the tour built for that moment. From the streets of Boston to the bridge at Concord where the first shots rang out, this private 6-hour car journey traces the exact geography of revolution. You will walk Harvard Yard, cross the bridge that inspired a poem read around the world, stand at Lexington Green where farmers faced down the British Empire, and step inside Orchard House where Louisa May Alcott wrote the story of a new American family. Your private guide, fluent in your language, connects every stop to the nation that was born here 250 years ago. Private transport keeps the day seamless. No crowds, no waiting, no compromise. This is not a sightseeing tour. This is a reckoning with the places that made America possible. Boston. Cambridge. Lexington. Concord. In America's 250th year, there is no more powerful journey you can take.
Duration: 6 hours
- Private tour
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Boston Walking Podcast Tour Tide Spring and Common
Ralph Waldo Emerson claimed Boston's streets were laid out by wandering cows. He was wrong. On this walking journey through downtown Boston, trace the physical realities that actually determined the colonial street pattern: William Blaxton's freshwater springs, strictly managed communal pasturage rules on the Common, and the commercial wharf grants that crept across tidal mudflats. Uncover buried canals, lost shorelines, and the true legal mechanisms that shaped early Boston.
- A 2.7 km self-guided tour with 8 stops over 112 min
- Ideal for travelers interested in Urbanism, Infrastructure & Innovation and History & Memory
- Immersively told in a podcast style by experts and locals
- Matching audio content, AI guide and navigation through the app
Duration: 1 hr 52 min
- Free cancellation