For over 30 years, Old Town Trolley Tours has provided sightseeing tours highlighting some of the most fascinating cities in America. Hop on and off all day while experiencing Transportainment, a delightful combination of transportation and entertainment. Our comfortable enclosed trolleys allow you to experience elevated viewing come rain or shine! Old Town Trolley is the best way to experience all the must-see places in the city you’re visiting
Old Town Trolley Tours (trolleytours.com) has 8 customer reviews on Five Star Index, with an average rating of 3.5 out of 5.
Also known as
trolleytours.com
Website
trolleytours.com
Category
Activities & Tours
Location
Key West, Florida
Listed on Five Star Index
2026
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Most recent review: March 2026.
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Abe and Buckeye are THE BEST! Abe is spot on with every detail we need. Abe had it all nicely organized for my group of 8th grade students and staff. Buckeye is the driver and we have used Old Town Trolley for many many years with our 8th grade students and have never been disappointed. Thank you to the Trolley Tours Team!
PK
Pennie K.
Lots of waiting
We waited while trolleys went past full. Then when we finally got on our trolley broke down and we finally got a bus to come get us and then we had to get off and transfer to another trolley where we waited again for a trolley that could hold all of us. All we wanted to do was ride through Boston to see the sights, before deciding where to go see a sight.
JR
Jessica R.
Must Ride the Hot Mess Express
⭐️⭐️⭐️⭐️⭐️
All Aboard the Hot Mess Express — A Must-Do in St. Augustine!
As a frequent visitor (and aspiring future resident!) of this historic gem of a city, I’ve done my fair share of tours — but Alicia’s trolley, affectionately dubbed the Hot Mess Express, is an absolute standout! 🔥🚋
Don’t let the name fool you — this ride is anything but a mess. It’s a perfectly curated blend of authentic history, laugh-out-loud humor, and even a few sing-along moments that kept our entire trolley thoroughly entertained from start to finish. Alicia’s passion for the city shines through with every pun, every punchline, and every historical tidbit she weaves into the ride.
Even in the Florida heat, the trolley was cool, comfortable, and surprisingly refreshing — the breeze was a welcome gift, and the ride itself was smooth and accessible for all ages and abilities. It truly allows anyone to experience the romance and charm of St. Augustine in comfort and style.
We laughed, we learned, and we sang — and I left more in love with this city than ever. Thank you, Alicia, for making today such a memorable and magical part of our summer adventure!
#HotMessExpress #StAugustineTrolley #BestTourGuideEver #HistoryWithHumor #CoolRideHotDay #StAugustineLove #CulturalGem #RideLaughLearn #HistoricCityVibes
AG
Angela G.
Really good tour of San Diego
Really good tour of San Diego. Our guide Kimmy was very informative and entertaining and we had a lovely trip seeing all the sights in a beautiful old trolley bus. It was well worth the price . We got tickets from a booth by the pier and got straight on a bus. There was very clear commentary all the way and when we changed buses in the old town( because we got on half way through the tour) we had another lovey and very funny driver Benjamin. I would highly recommend this tour to give a very good overview of San Diego- thoroughly enjoyable.
JT
John T.
WARNING: Book at Your Own Risk
WARNING: Use at your own risk!
Terrible experience. NO Customer Service.
Expensive, Two tickets were $110.
We made two stops.
After the 3rd stop, the trolley never returned.
They were still in operation but they refused to stop at the designated stop.
Not One but TWO trolleys passed us right by as we stood at the designated stop, which happened to be RIGHT IN FRONT of their storefront by Boston Commons.
We called the number on the brochure FIVE (5) times to try to figure out what was going on.
Twice we were hung up on.
Twice we went to voicemail.
Once the call was answered and a guy told us to wait right where we were and a trolley would be along in 20 minutes.
Forty minutes later, no trolley had arrived.
We had to WALK all the way across Boston to get back to our hotel.
Then, I called the next day to complain.
I was emailed a refund form to fill out.
It was extensive and I had to attach a copy of my receipt.
It's been two weeks now and I haven't even received acknowledgement of them receiving the form.
I hope this review costs them Many, Many times more than the $110 they scammed us out of.
Expensive, no commitment to service, worst customer service I've ever experienced, cast a bad memory over our entire trip to Boston.
Screw this company - the only way they're still operating is they take your money and SCREW YOU!
AM
Alistair M.
Not happy
Took a tour in Washington DC last week and was overcharged (for 2 persons rather than one). No response to my requests for a refund - most unhappy with service to date
TG
Trinity G.
Give James a raise
Give James a raise. Don't get me wrong, all the tour guides were great and very nice. But James is one of a kind. He is funny, warm-hearted, and very personable. We, my boyfriend and I, absolutely loved James and we always looked for him when we saw one of these trolleys. He really made the tour one of our favorite experiences during our trip. As for the tour itself, it is great. Lots of cool history and beautiful sites. Definitely recommend.
LU
luis
Love this tour company !!
Love this tour company !!! the drivers are super pro