Old Town Trolley Tours Key West
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Our take
By Matt Spaulding, Founder and writer
The trolley does two jobs at once, and it helps to know which one you are buying. The first is orientation: a 90-minute loop of roughly 13 miles, narrated by a conductor, past more than 100 sites as you roll through Old Town and Bahama Village. The second job is transport. Key West parking is the genuine headache, and Old Town Trolley's own advice is to leave the car at the city garage on Grinnell Street (300 spaces, first come first served, $6 an hour plus tax and a $48 daily rate plus tax as of August 2026) or the paid lots by Mallory Square, then ride. Here is the catch: it is a narrated loop on public streets shared with scooters, pedicabs and cruise-ship crowds, so it is slow, and 90 minutes is a good-day number. Hopping off costs you real time, because trolleys reach each stop every 20 to 30 minutes, and the operator states plainly that at peak times it cannot guarantee a seat on every trolley. Three hop-offs can eat an afternoon in waiting. The trolleys are open-air with no air conditioning, which is lovely in February and punishing in August, though isinglass curtains roll down when it rains. The last trolley leaves Mallory Square at 4:30pm, so a late start wastes the ticket.
Quick facts
- How long
- About 90 minutes for the full loop, roughly 13 miles, if you stay on board the whole way. Hop off two or three times and it fills a half day or more.
- Hours
- First tour at 9am, last one out of Mallory Square at 4:30pm. Runs 364 days a year, closed the last Saturday in October for Fantasy Fest.
- Getting there
- Board at any of the 13 stops. Ticket booths sit at Mallory Square (401 Wall Street), Simonton and Greene, Truman Avenue at Duval, and Angela at Duval.
- Parking
- The operator points drivers to the city garage at 301 Grinnell Street, corner of Caroline and Grinnell, or the paid lots near Mallory Square. The garage has 300 spaces, first come first served, open 24 hours.
- Included
- Conductor narration covering more than 100 points of interest, two guided walking tours, a coupon book, and a real-time trolley tracker map. Tickets come as one day of unlimited reboarding or two consecutive days.
- Best for
- A first orientation day on the island, cruise passengers with a few hours, and anyone who would rather not walk Old Town in August heat. Open-air trolleys, so no air conditioning.
Where it is
Stop 1 at Mallory Square, 401 Wall Street, Old Town, Key West
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How long does the Key West trolley tour take?
The full loop is about 13 miles and takes roughly 90 minutes if you ride it all the way around without getting off. Once you start hopping off, plan on a half day or more, since trolleys reach each stop every 20 to 30 minutes. Two or three stops plus the ride around is a comfortable day.
Where can you board the trolley?
Any of the 13 stops works, and you can start wherever suits your morning. Ticket booths are at Mallory Square (401 Wall Street), the corner of Simonton and Greene, Truman Avenue at Duval, and Angela at Duval.
Where do you park in Old Town Key West?
Old Town Trolley points people to the city parking garage at 301 Grinnell Street, at the corner of Caroline and Grinnell, or the paid lots near Mallory Square. The garage holds 300 cars on a first come, first served basis and stays open 24 hours; the city lists a $6 hourly rate plus tax and a $48 daily rate plus tax as of August 2026. Paying there also covers free rides on the city's own bus routes for everyone in your vehicle, which is a separate service from the trolley.
Is the ticket good for one day or two?
Both versions exist. The standard ticket gives you one day of unlimited reboarding, and there is a two-day ticket valid across two consecutive days. Two days is worth considering if you want to combine museum stops with the ride, since the last trolley leaves Mallory Square at 4:30pm each day.
Do you need a reservation?
No, the standard daytime hop-on hop-off tour is first come, first served and does not take reservations. Themed tours are the exception and do require them. At busy times the operator says it cannot guarantee a seat on every trolley, and that field dispatchers send another vehicle to stops where guests could not board.
What do you get besides the ride?
Narration from a conductor covering more than 100 points of interest, two guided walking tours, and a coupon book of discounts around the island. There is also a tracker map showing where trolleys are in real time, which is useful before you commit to standing at a stop. Museum and attraction admissions are not included unless you buy one of the combination packages.