Boston's Best: Self-Guided Driving Tour of Iconic Landmarks
3
Places: 28 POIs
Distance: 10.65 mi
Duration: 1h:31m
GPS-guided narration through
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Apple CarPlay
Android Auto
Tour #2593
Boston: Self-Guided Driving Audio Tour of Iconic Landmarks incl. Old North Church
About this English self-guided 1h:31m driving tour in Boston, MA
Welcome to Boston, Massachusetts—one of America’s oldest cities and the place where history, culture, and innovation all come together. Founded in 1630 by Puritan settlers, Boston grew from a small colonial town into the “Cradle of Liberty,” where the seeds of the American Revolution were planted.
This is the city of the Boston Tea Party, the Midnight Ride of Paul Revere, and the first reading of the Declaration of Independence. On these streets, ordinary citizens took extraordinary steps that changed the course of history. But Boston isn’t just about revolution—it’s also about reinvention. From its early days as a seaport and marketplace, to its rise as a center of education, science, and medicine, Boston has always been a city that pushes boundaries.
You’ll see that mix everywhere we go. Cobblestone streets in the North End still echo with the footsteps of patriots, while grand boulevards like Commonwealth Avenue showcase 19th-century elegance. Modern towers like the Hancock Building rise beside historic treasures like Trinity Church. And neighborhoods from Beacon Hill to Back Bay all tell a different part of Boston’s story.
Along the way, we’ll pass world-class cultural landmarks like the Museum of Fine Arts, Fenway Park, and the Boston Public Library. We’ll point out the quirky spots too—from the Cheers Bar to the bench where Robin Williams filmed Good Will Hunting. And of course, we’ll explore the flavors of Boston, from North End cannoli to the city’s obsession with seafood and chowder.
Boston is also a city of firsts: the first public school, the first public library, the first subway, and the first great American ballpark. Famous figures like Benjamin Franklin, John Adams, Paul Revere, Louisa May Alcott, and Martin Luther King Jr. all have ties here, leaving their mark on both the city and the nation.
So buckle up as we set off on this driving tour of Boston. We’ll blend history with fun facts, point out landmarks on your left and right, and give you a true sense of what makes this city so unique. From revolution to Red Sox, from cobblestones to skyscrapers—this is Boston. Let’s hit the road!
Top landmarks on this tour
Old North Church- Fenway Park
- Boston Common
- Paul Revere's Historic Home
- Old State House
- Boston Tea Party Ships & Museum
- 1For the best experience, begin at the tour's recommended starting point and follow the stops in order.
- 2Want to start somewhere else? Simply use Start At on the tour screen, before tapping Start Tour, to begin from any stop.
- 3Need to detour or skip a stop along the way? Tap Tour Assistant (
![UCPlaces AI Bot Icon]()
) to use Force Play, Skip, and Back, for full flexibility.
) to use Force Play, Skip, and Back, for full flexibility.
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Places (POIs) visited during this tour
Place #1
![Map Pin]()
Recommended Starting Point
Distance: 0.00mi
, Attraction : Historic Cemetery (Recommended selfie spot).
36 Hull St, Boston, MA 02113, USA
Copp’s Hill Burying Ground – Kicking Off in the North End
We’re kicking off our Boston driving tour here at Copp’s Hill Burying Ground on your left. It's the city’s second-oldest cemetery, dating back to 1659. This hillside resting place offers the perfect starting point because it combines history, Revolution, and the atmosphere of Boston’s oldest neighborhood—the North End.
From here, British troops once aimed their cannons across the harbor during the Battle of Bunker Hill in 1775. But long before that, Puritan ministers, merchants, shipbuilders, and everyday colonists were buried here. Among the most famous are Increase and Cotton Mather, powerful Puritan preachers, and Robert Newman, the Old North Church sexton who hung the lanterns for Paul Revere’s legendary ride.
As you look at the weathered headstones, notice the carved winged skulls, hourglasses, and grim reminders of mortality—classic Puritan symbolism. This isn’t just a burying ground; it’s a window into how 17th- and 18th-century Bostonians lived, died, and remembered their faith.
And beyond the walls of Copp’s Hill is today’s North End—a neighborhood buzzing with Italian cafés, bakeries, and narrow streets that still feel like Old Boston. So with this mix of the colonial past and vibrant present, we kick-start our journey through Boston’s history.
From here, British troops once aimed their cannons across the harbor during the Battle of Bunker Hill in 1775. But long before that, Puritan ministers, merchants, shipbuilders, and everyday colonists were buried here. Among the most famous are Increase and Cotton Mather, powerful Puritan preachers, and Robert Newman, the Old North Church sexton who hung the lanterns for Paul Revere’s legendary ride.
As you look at the weathered headstones, notice the carved winged skulls, hourglasses, and grim reminders of mortality—classic Puritan symbolism. This isn’t just a burying ground; it’s a window into how 17th- and 18th-century Bostonians lived, died, and remembered their faith.
And beyond the walls of Copp’s Hill is today’s North End—a neighborhood buzzing with Italian cafés, bakeries, and narrow streets that still feel like Old Boston. So with this mix of the colonial past and vibrant present, we kick-start our journey through Boston’s history.
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Place #2
![Map Pin]()
Distance: 0.07mi
, Attraction : Historic Church (Recommended selfie spot).
5 Hull St, Boston, MA 02113, USA
Old North Church – “One If by Land, Two If by Sea”
Right ahead is Old North Church, officially named Christ Church in the City of Boston. Built in 1723, it’s the oldest surviving church building in the city and one of the most iconic landmarks of the American Revolution.
On the night of April 18, 1775, two lanterns were hung in its steeple, signaling that British troops were marching to Lexington and Concord by sea. That signal—“one if by land, two if by sea”—set Paul Revere’s midnight ride into motion, warning the colonists that the Redcoats were on the move.
The church itself is a beautiful example of Georgian architecture, with its tall white steeple rising above the narrow streets of the North End. Inside, you’ll find old box pews, crystal chandeliers, and memorial plaques to the patriots who worshipped here.
The Old North is more than just a historic site—it’s a symbol of Boston’s revolutionary spirit. From this small steeple, a signal sparked events that would lead to the birth of a nation.
On the night of April 18, 1775, two lanterns were hung in its steeple, signaling that British troops were marching to Lexington and Concord by sea. That signal—“one if by land, two if by sea”—set Paul Revere’s midnight ride into motion, warning the colonists that the Redcoats were on the move.
The church itself is a beautiful example of Georgian architecture, with its tall white steeple rising above the narrow streets of the North End. Inside, you’ll find old box pews, crystal chandeliers, and memorial plaques to the patriots who worshipped here.
The Old North is more than just a historic site—it’s a symbol of Boston’s revolutionary spirit. From this small steeple, a signal sparked events that would lead to the birth of a nation.
Tour itinerary stops | Additional places you'll see on this self-guided tour
Place 1
Copp’s Hill Burying Ground – Kicking Off in the North End
Place 2
Old North Church – “One If by Land, Two If by Sea”
Place 3
The Boston Waterfront – Harbor of History
Place 4
Christopher Columbus Waterfront Park & New England Aquarium
Place 5
Paul Revere's Historic Home
Place 6
North End – Boston’s Little Italy
Place 7
Boston’s North Market – Part of Faneuil Hall Marketplace
Place 8
Old State House – Birthplace of the American Revolution
Place 9
Post Office Square & Norman B. Leventhal Park – From Asphalt to Oasis
Place 10
Boston Tea Party Ships & Museum – A Revolution on the Water
Place 11
Martin’s Park – A Playground of Hope
Place 12
Summer Street Bridge – Gateway to the Seaport and Back Bay
Place 13
Citizens Bank Opera House – Boston’s Gilded Theater
Place 14
Boston Common – America’s Oldest Public Park
Place 15
Beacon Street – Boston’s Grand Boulevard
Place 16
Massachusetts House of Representatives – The People’s Chamber
Place 17
Boston Fallen Firefighter Memorial – Honoring Bravery
Place 18
Pinckney Street – Life on Beacon Hill
Place 19
Acorn Street – Boston’s Most Photographed Street
Place 20
Cheers Bar – Where Everybody Knows Your Name
Place 21
Robin Williams Bench – Good Will Hunting’s Legacy
Place 22
Commonwealth Avenue – Boston’s Grand Boulevard
Place 23
Copley Square – Boston’s Architectural Showcase
Place 24
Boston Public Library – A Palace for the People
Place 25
Newbury Street – Boston’s Style Mile
Place 26
Fenway Park – America’s Most Beloved Ballpark
Place 27
Back Bay Fens
Place 28
Museum of Fine Arts
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Have any questions about this tour? Or a general travel / self-guided tours question? That's completely natural
+ How long does this tour take?
Most travelers complete this tour in approximately 1.5 to 1.5 hours, depending on pace, time spent at each stop, and optional detours. Having said that, please remember that self-guided tours are extremly flexible (you can start, pause, continue anytime) and everyone has their own pace.
+ What does this tour include?
This self-guided driving tour includes 28 stops, covering top attractions such as Copp’s Hill Burying Ground – Kicking Off in the North End, Old North Church – “One If by Land, Two If by Sea”, The Boston Waterfront – Harbor of History, Christopher Columbus Waterfront Park & New England Aquarium, Paul Revere's Historic Home.
+ Where does the tour start?
The tour starts at Copp’s Hill Burying Ground – Kicking Off in the North End (Address: 36 Hull St, Boston, MA 02113, USA). You can begin the tour there or join from any stop along the route.
+ What type of tour is this?
This is a self-guided driving tour designed to be completed by car, covering scenic routes, city highlights and optional key stops.
+ Can I do this tour at my own pace?
Yes, this is a self-guided driving tour, so you can start anytime and explore at your own pace. You can pause, skip stops, or spend more time at places that interest you. You can even split it into multiple days. Explore however feels right for you. The only vaiables that might affect your pace are speed limits and traffic congestion.
+ Do I need a car for this tour?
Yes, this is a driving tour, designed to be completed by car, with stops spread across different locations connected by a driving route.
+ Do I need anything in order to take the tour?
There are two things that you need - 1. A mobile phone (with the UCPlaces app installed and active location services, and a cellular data plan with a decent signal for downloading the tour). 2. A car. Here are some recommendations for a great experience: 1. Make sure your phone is fully charged and bring a charging cable for your car. 2. Connect your phone to the car speaker system via bluetooth or use our CarPlay/Android Auto option for the best experience.
+ How will I navigate from point to point during the tour?
The tour uses GPS-based navigation through the UCPlaces app, with automatic audio playback and step-by-step directions between stops. This works great either directly from your phone, or while connected to your car's multimedia system and using our CarPlay or Android Auto options. Just follow the route and listen to the audio guide. Use the resume feature to continue from where you recently stopped (or closed the app). Easily skip or go back to stops.
+ What known landmarks and main sites does this tour have?
The top landmarks and main sites on this tour include Old North Church, Fenway Park, Boston Common, Paul Revere's Historic Home, Old State House and Boston Tea Party Ships & Museum. In total, the tour has 28 points of interest along the route.
+ Is this tour suitable for families or groups?
Yes, self-guided tours are ideal for families and small groups, allowing everyone to explore comfortably without being tied to a fixed schedule.
+ What makes a self-guided tour better than a guided tour?
Self-guided tours are more flexible, affordable, and personalized. You can avoid crowds, choose your pace, and focus on the stops that interest you most.
+ I installed the app and it's now asking for GPS and media access permissions, why?
The app is your tour-guide, it needs to know where you are located on the map to be able to trigger the points of interest. It also needs access to audio and media files to provide you with this experience.
+ What happens if there are unexpected roadblocks or navigation issues?
We have been working hard to deliver a great experience. Though you may run into unexpected obstacles (the world is constantly changing), our app has multiple features and mechanisms in place to help you overcome them, including: AI assistance, force play an audio if you can't reach the stop, skip or return to stops, automatic rerouting and more.
+ Can I take the tour in my language?
Though all of our tours are primarily in English, many tours are muyltilingual (including: Spanish, German, Portuguese, French, Japanese, Hebrew, French, Arabic and more...). The tour language options depend on the specific tour - You can easily check which languages are available in the tour screen!