Boston's Best: Self-Guided Driving Tour of Iconic Landmarks
Places: 28 POIsDistance: 10.65 miDuration: 1h:31m
Tour #2593
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!
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.
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.
Tour itinerary stops | Additional places you'll see on this self-guided tour
Place 1Copp’s Hill Burying Ground – Kicking Off in the North End
Place 2Old North Church – “One If by Land, Two If by Sea”
Place 3The Boston Waterfront – Harbor of History
Place 4Christopher Columbus Waterfront Park & New England Aquarium
Place 5Paul Revere's Historic Home
Place 6North End – Boston’s Little Italy
Place 7Boston’s North Market – Part of Faneuil Hall Marketplace
Place 8Old State House – Birthplace of the American Revolution
Place 9Post Office Square & Norman B. Leventhal Park – From Asphalt to Oasis
Place 10Boston Tea Party Ships & Museum – A Revolution on the Water
Place 11Martin’s Park – A Playground of Hope
Place 12Summer Street Bridge – Gateway to the Seaport and Back Bay
Place 13Citizens Bank Opera House – Boston’s Gilded Theater
Place 14Boston Common – America’s Oldest Public Park
Place 15Beacon Street – Boston’s Grand Boulevard
Place 16Massachusetts House of Representatives – The People’s Chamber
Place 17Boston Fallen Firefighter Memorial – Honoring Bravery
Place 18Pinckney Street – Life on Beacon Hill
Place 19Acorn Street – Boston’s Most Photographed Street
Place 20Cheers Bar – Where Everybody Knows Your Name
Place 21Robin Williams Bench – Good Will Hunting’s Legacy
Place 22Commonwealth Avenue – Boston’s Grand Boulevard
Place 23Copley Square – Boston’s Architectural Showcase
Place 24Boston Public Library – A Palace for the People
Place 25Newbury Street – Boston’s Style Mile
Place 26Fenway Park – America’s Most Beloved Ballpark
Place 27Back Bay Fens
Place 28Museum of Fine Arts
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A self-guided audio tour taken via the UCPlaces app [Android / iOS (iPhone) / Apple CarPlay].
Tour route map and in-app GPS navigation (via the UCPlaces app).
Audio stories for places visited during the tour.
Apple CarPlay connection (for iOS users); for a seamless driving tour experience.
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Earphones (highly recommended).
Smartphone.
Any kind of transportation (including tickets and passes).