Ah, Boston! The cradle of the American Revolution, home of the Red Sox, and land of the most perplexing accent this side of the Atlantic. But let’s face it, exploring this historic city on foot can leave you with blisters bigger than Paul Revere’s ego. Enter the Old Town Trolley Hop On Hop Off Tour – the perfect way to see Beantown without wearing out your beans (that’s “feet” in Boston-speak, or so I’ve been told by a guy named Sully at a bar). This is by far the best way to explore! We always do the trolley tour on our first full day in a new city to get a lay of the land and find the hot spots we want to visit later in our trip.
All Aboard the Time Machine on Wheels
Picture this: You’re sitting comfortably in a charming trolley that looks like it drove straight out of a Norman Rockwell painting, but with better suspension. The Old Town Trolley isn’t just a mode of transportation; it’s a time machine with wheels, ready to whisk you through 400 years of history with a total of 18 different stops!
There are a lot of bus tours offered in a city like Boston, but what makes Old Town Trolley the best is the live narration from the driver! At our first stop, we met our driver King Knight. He’d only been on the job about 45 days, but he was already a seasoned pro. His personal anecdotes about his experiences growing up in Boston to proposing to his wife at Fogo de Chao made the experience that much better. He was engaging, funny, and detailed with his tour.
The Freedom Trail: Now with 100% Less Walking
First stop: the Freedom Trail. This 2.5-mile red brick path connects 16 historically significant sites. On foot, it’s a trek that might have you wishing for the stamina of a colonial minuteman. But from the trolley? You’re gliding through history like a patriot on a Segway.
As you roll past sites like the Paul Revere House and the USS Constitution, your tour conductor (we had King Knight who was phenomenal) regales you with tales of the American Revolution. Did you know that Paul Revere never actually shouted “The British are coming!”? Apparently, it was more of a whisper campaign. Colonial Twitter, if you will.
Boston Common: Where the Grass is Greener, and the History is Juicier
America’s oldest public park, Boston Common, has seen everything from grazing cows to protests, public hangings to victory gardens. Today, it’s a picturesque spot and the weather was absolutely gorgeous with temps in the mid 70s and sunshine. Plenty locals were sunbathing, having picnics, or having an intense workout. Fun fact: In the 1960s, you could pay $3 to “Rent-A-Beatle” and have them come play in the park. Sadly, this service is no longer available, much to the dismay of tribute bands everywhere. But make sure to check out the “Make Way for the Ducklings” Sculpture!
Cheers: Where Everybody Knows Your Name (If Your Name is Norm)
No trip to Boston is complete without a stop at the bar that inspired the hit TV show “Cheers.” The trolley will drop you off at the Bull & Finch Pub, now officially called Cheers Beacon Hill. The building was undergoing renovations so there was scaffolding and some tools, but you could still enjoy a cold one at Cheers. Warning: Shouting “NORM!” as you enter may result in confused stares or, worse, someone actually named Norm answering you.
Prudential Center and the View Boston Observation Deck
The Prudential Center in Boston, Massachusetts, is not just a shopping mall but also houses one of the city’s iconic skyscrapers, the Prudential Tower, which stands as the second-tallest building in Boston. At the top of this tower lies the View Boston Observation Deck, spread across the 50th, 51st, and 52nd floors. This observation deck offers visitors a 360-degree view of Boston, providing breathtaking vistas that extend up to 33 miles on clear days. Beyond mere sightseeing, View Boston enhances the experience with interactive exhibits, dining options at The Beacon, and an open-air roof deck, making it a comprehensive urban experience above the city. This was a highlight of our time on the hop on hop off bus because it wasn’t busy and the weather was perfect. It was nice to have a drink, relax, and soak up the Boston cityscape.
The Tea Party Ships: Brewing Up Revolution
The Boston Tea Party Ships & Museum is an interactive museum located at the Congress Street Bridge in Boston, Massachusetts, where the famous Boston Tea Party took place in 1773. Visitors can step aboard authentic replica ships, the Eleanor, Beaver, and Dartmouth, and participate in a reenactment of the event where they can throw “tea” overboard. The museum offers immersive experiences through multi-media presentations, a holographic meeting with Samuel Adams, and the chance to explore below-deck areas to learn about the life of colonial sailors. Beyond the ships, the museum’s “Time Tunnel” exhibit provides a journey through the American Revolution, highlighting the significance of the Tea Party in the lead-up to the Revolutionary War. While we did not tour the museum, it was a great photo op!
Hop Off, Hop On: The Beauty of Flexibility
The real beauty of this tour is in its flexibility. Much like a Bostonian’s loyalty to their sports teams, you can hop on and off as much as you like throughout the day. Spend an hour exploring Quincy Market’s food stalls, or take a quick peek inside the Massachusetts State House. The trolley operates on a frequent schedule, ensuring that visitors don’t have to wait long to catch the next ride. This service was particularly beneficial for our first time visiting Boston. We were only in town 4 days so this was an efficient way to see all of the attractions in a short amount of time without the need for ordering a dozen Ubers!
The Wrap-Up: Boston Trolley Tour in a Nutshell (or a Baked Bean Can)
After a full day of hopping on and off, you’ll have seen more of Boston than most locals do in a year (except for the ones who drive for ride-sharing apps – they’ve seen things, man). You’ll have traveled through time, across revolutions, and probably eaten your weight in clam chowder. We enjoyed our tour so much, that we ended up booking Old Town Trolley’s Ghosts and Graveyards tour that evening!
The Old Town Trolley Hop On Hop Off Tour is more than just a convenient way to see the city. It’s a journey through the heart and soul of Boston, guided by locals who love their city more than Tom Brady loves avocado ice cream. So, the next time you find yourself in Boston, hop aboard the Old Town Trolley. It’s a wicked smart way to explore the city, learn some history, and give your feet a break. Just remember: it’s pronounced “pah-k the cah in Hah-vad Yahd,” and yes, they’re still a bit touchy about that whole tea thing.
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