☆☆☆☆☆
★★★★★
1262 reviews
Old Town Trolley Tours of Boston
4.3
Boston is a beautiful city filled with historic sites that helped shape colonial America.
Maximize your time for sightseeing by taking Boston shore excursions for cruise ship guests with Old Town Trolley.
For over 40 years, Old Town Trolley has brought guests closer to attractions like the Cheers Bar, Beacon Hill, USS Constitution, and the North End just to name a few.
Purchase tickets online or through our ticket depots.
Join us as we turn back the pages of history and relive the bustling seaport days of colonial Boston. Feel the drama of revolution in America! We operate the only “stadium” trolleys in the city and Boston’s largest fleet of sightseeing vehicles with the most frequent departures, so you can tour at your own pace. Plus, we offer unlimited re-boarding privileges at 18 convenient stops. Our expert tour conductors will show you all the major sights such as Beacon Hill, the CHEERS bar, Old North Church, Bunker Hill Monument and Boston Public Garden.
Guests are met on the pier and escorted to private vehicles at the cruise terminal. From there the trolleys will proceed to our main tour route (stops #1-14). Hop off and back on at conveniently located stops designed to maximize your time here in Boston. Your “Must Do” Old Town Trolley Tour of Boston will give you an inspiring overview. Our expert conductors will show you all the major sights such as Beacon Hill, the CHEERS Bar, Old North Church, Bunker Hill Monument, Quincy Market, Faneuil Hall, and the Boston Public Garden. Every trolley on our main tour route (stops #1-14) will proceed to drop you off at the cruise ship after leaving stop #14.
We recommend purchasing Tour Option 2 from your Shore Excursion Desk.
The distance to your trolley depends on where your cruise ship is docked. There are three different berths where cruise ships dock and the walking distance from them varies.
The closest trolley stop is #16. Click here for walking directions.
Please check with your cruise line to determine where your ship will be docked during your visit. It’s also important to know that any trolleys parked directly in front of the cruise terminal are there for guests who have purchased Tour Option 2 from their Shore Excursion Desk and are not available to the general public.
To return to any of the piers, adults must have both their ship’s card (which usually doubles as the room key) and a valid photo identification (passport, driver’s license, etc.)
Discover the rich history of Boston with Old Town Trolley Tours and see the best first! Whether you’re in town for a short visit or a few hours during your cruise vacation, here are the top 5 reasons to join us for your next adventure:
Join us aboard the Old Town Trolley to explore the best of Boston with comfort and style, even if your time in the city is short!
Our tour guide, Phoenix, was very knowledgeable, had a good wit, and shared many, many nuggets of information that made the trip interesting and full of energy. Even when we asked about other points of interest we thought he might know about he was able provide name and an interesting nugget about it. He met children’s interests as well as adults. Will definitely tell others about your service and have them look for Phoenix. Thank you all.
Today, we did the last tour of the day with Scribe as our tour guide and he was phenomenal! He was knowledgeable, extremely affable and made us feel like family. My husband said it was money well spent and made our trip! Such an asset to your company! Thanks for your service today, Scribe.
Your driver, Maureen, was by far the most memorable part of our trip. Her enthusiasm and energy lit up the entire trolley. She’s is passionate about her home town, packed full of tons and tons of information, and lovely to make the entire experience a GREAT one. My friends and I cannot wait to visit Boston again soon, and are hoping to have Maureen as our trolley driver. Thank you for a great traveling experience…
My husband and I were in Boston after 25 years. We decided last minute to take one of your trolley tours. We had such a wonderful time! I learned more about Boston on that tour than in the seven years I lived there. Our guide Hugo was the BEST! He kept us laughing the whole time…
I’m grateful for the hop on/off tours; without them my aging parents would have struggled to see Boston; and they loved hearing the history. Perfect segue: We had several different guides… Book was far/away our favorite. Good storyteller, quick wit, quite helpful. Interesting guy… But seriously, really enjoyed his tour.
My girlfriend and I wanted to say how great Billy Ketch was. Not only was he extremely knowledgeable about your great city, his sense of humor and personality made this an unforgettable experience.
I am an International Tour Director from Britain. I have just gotten my schedule and will be giving the heads up for the Old Town Trolley Tours which I hope all my pax will be taking while on their stay in Boston. I was given passes to go onto the other trolleys and NO COMPARISON to yours. Everyone is great and I have gotten to know most of the drivers from years past. They are the best and have the best tour…
My friends, husband and I were on the Trolley with Billy last week and had the BEST tour! Having been an American History teacher for 30 years, I was truly fascinated with Billy’s knowledge and experience with the tour! Even my friends who are not especially interested in History, thought that Billy was the greatest tour guide they had ever had.
This was a great way to see the city. The two tour guides were both friendly and EXTREMELY knowledgeable. I would recommend this tour to anybody visiting Boston. I even dazzled my friends later in the week with all that I knew of the city. Thanks for an awesome visit!!!
Just did a Tour with JD last weekend. He was awesome…… the tour was the best part of our trip to Boston. Not sure if you have a survey….. just wanted you to know he got an A+++ Thank you!
…We took your tour and had a fabulous time learning… What made the tour memorable was our conductor, ‘Townie’. He made the tour one of the highlights… and having been on other operators in various cities, I must applaud him, as they’re the exact type of conductor you want on an introduction to the city…
We rode with two drivers today, Miss Jackson and Crafty. They are both PHENOMENAL. They made our trips around town outstanding and informative. Thank you so much for hiring the best! Make sure to compensate them above and beyond so that they continue to rep your company and the city of Boston so spectacularly!
I wanted to reach out about the absolutely fantastic tour we had of Boston. We were picked up from the Cheers stop by your driver, Twin, who got us through downtown rush hour safely and with the most humorous commentary that was one of the highlights of the trip. Not only did he keep up on discussing the points of interest, but also gave us good information on what not to miss when we got out on foot…
My family and I visited Boston this past week… While all of your drivers were knowledgeable and polite there was one that truly made the experience. Ms. Beantown was not only super entertaining, she went out of her way to help my family with wheelchair assistance with her trolley AND onto another trolley…
As always, we had a great time doing your tour!… We had Miss Jackson! She was fantastic – that doesn’t even give her justice. She gave a great history of the city and sites, made some jokes and made the time we were on her trolley so enjoyable! She had a great personality and was just a bright star on our trip! Thank you for the opportunity to get to meet her and to take the tour!
My wife and I had North as our Tour Guide. We stayed on the bus from Stop 1 to the end… He was fantastic – driving a large bus on Boston’s streets would be an incredible skill alone, but to also have the ability to provide relevant and interesting historic information while driving is another major skill unto itself. North also did this while speaking loudly, clearly, and by keeping the passengers engaged – it was obvious he was also a lover of history and shared the information with excited passion.
I just wanted to let you know that, while we enjoyed our tour yesterday, we were especially impressed with two of your guides: Marilyn on the shuttle loop, and Regan. Both were pleasant, personable and went above and beyond.
We are two French tourists and got to do your trolley in Boston with La La. She was exceptional and made this tour so lively and interesting and fun. Such a great storyteller! Thank you.
The tour guide King Knight in Boston was fantastic! He provided a fascinating and funny tour and went the extra mile to make sure everyone got to where they needed to be in the end. He said he had only been on the job for 48 days, but he seemed like a seasoned vet! We truly appreciated him!
…The guides were so informative and entertaining, plus we saw so much of the city and that really helped us get oriented on our first day. The guides’ recommendations were spot-on and they had answers to every question thrown at them! After spending all day sightseeing on the trolley, we ended up on Crafty’s last tour of the day, and instead of rushing through the highlights so he could get home, he took the time to add anecdotes and initiate discussions with us. I will definitely look for Old Town Trolley Tours when I visit their other cities!
Our guide, Maureen, was really brilliant. She combined extensive knowledge with humor and had unbelievable get up and go. Nothing was too much trouble. You have a unique advantage over the competition.
We just returned from a visit to Boston where we took a wonderful ride on the Old Town Trolley. We need to let you know about the remarkable and entertaining guide we had – KING KNIGHT. First and most important, he was a safe driver and very knowledgeable about the history of Boston. But what made him special was his sense of humor. We all laughed throughout the trip… No one wanted to “hop off”… BEST EXCURSION of our eleven day cruise and we owe it all to KING KNIGHT!