10 Things to Know About Old Town Trolley Tours

Each time I step foot into a new city, I realize how much my high school history lessons have faded into the dark recesses of my memory. I noticed this recently while in St. Augustine, Florida, reading the informational signs at the historic Castillo de San Marcos National Monument. The fort was one of several stops we made on the Old Town Trolley hop-on-hop-off tour run by Historic Tours of America.

As we celebrate America’s 250th anniversary in 2026, it’s a great time to visit the cities where it all began. Consider a narrated trolley tours with the flexibility to hop off to see a site and then hop back on to continue.

This list of 10 things to know about Old Town Trolley Tours came together after our experiences with the tours in San Diego, St. Augustine, and Key West. Use the information to decide if a ride on the bright green and orange trolleys is right for you and see some of our favorite stops. You can also read 8 things to know about taking a guided tour for more tips and information.

This post contains affiliate links. If you purchase something, familyTravelsUSA may receive a small commission. As always, opinions are my own.

First, you should know that Historic Tours of America currently offers the Old Town Trolley Tour in 9 US cities to include San Diego, Washington, DC, St. Augustine, Boston, and Key West. They have even created a special term for their tours ”Transportainment®, a delightful combination of transportation and entertainment.”

The trolleys vary slightly in size and design, but you can generally expect a covered vehicle or larger bus-type trolley with big or open windows. After taking a few tours, we learned a few things we wanted to share. Hopefully these 10 things to know about Old Town Trolley Tours will answer all your questions and enhance your experience.

Should I Take a Tour on my First Day in a New City?

Absolutely! If there is one thing I have learned is that taking a tour early on is the best way to get to know a new destination. In St. Augustine, we discovered places to return to, including Flagler Memorial Presbyterian Church and St. George Street for shopping. The drivers provide a historical overview in an engaging manner, all while navigating the busy streets and introducing the neighborhoods. With some stops clustered together, you can decide to walk as little or as much as you want.

How Much Time Should I Allow?

Maximize your ticket with a full day on a tour. Having said that, we spent about 4 hours each in both St. Augustine and San Diego and were able to see quite a bit. Going inside museums and other attractions will definitely cut into time spent on the trolley. Plus, each stop takes time to allow passengers to board, drivers to switch, etc. So, when they say the tour is 90 minutes long, that is just the time spent on the trolley for the entire route.

What is the Cost of the Tour?

The tour costs vary from city to city and change throughout the year. During March in St. Augustine, there was a spring break price surge with tickets at roughly $41 but then dropping back to $36. In San Diego, prices average between $48 and $56 dollars.

Is it Worth the Money?

We have visited the majority of the 9 cities that offer the tour and agree there is much to see! The Old Town Trolley Tour offers a hassle-free alternative to sightseeing that takes the stress out of city driving and parking. Yes, you could use your own car, a ride-share, or public transportation to get around, but the history lessons along with the efficiency of getting around is worth the price.

What Are the Ticket Options?

Browse any of the Old Town Trolley city sites and you will see a handful of ticket options. This includes combination tickets with other attractions like in St. Augustine, as well as tickets to the popular Ghosts & Gravestones Tour in several locations. A 2-day ticket option provides a discount and gives you more time to visit attractions or just use the trolley to get around. Ticket booths are scattered around each city.

Is It Easy to Hop Back On?

In most cases, there was no issue grabbing a seat on the next trolley. The one exception was in San Diego when we visited Coronado. Folks were waiting in line to board, and we had to wait for a second trolley to arrive about 10 minutes later. I imagine this may be true at popular attractions in other cities as well. Keep in mind that your ticket is good all day, so even if you are done sightseeing you can use the trolley to get across town.

Should I Get Off at Every Stop?

Each city tour has a helpful website with maps, details of the stops, and information about additional costs. To get the most bang for your buck, use the map and decide ahead of time which stops interest you the most. Many of these cities have museums that you may want to spend more time in so plan accordingly. In San Diego, stops like the Maritime Museum and Balboa Park are home to several museums where you will want to spend more time.

Can I Join at Any Stop on the Route?

Use the on-line Trolley Tracker to see real-time trolley movement. You can usually start the tour at the most convenient stop as long as you have pre-purchased a ticket; however, note that if it is early in the morning and the trolleys are just starting, it may be a while if you are waiting at one of the later stops. If you purchase a ticket online or through a hotel, and not at a ticket booth, expect to exchange your paper ticket for a wearable sticker at some point on the ride.

Do I Have to Pay Extra to Enter Attractions?

Yes, in many cases there are attractions that require admission. The website for each city outlines this information. Under each stop, use the “more info” tab to get details for specific attractions. So if drinking from the Fountain of Youth in St. Augustine is on your list, be prepared to spend almost $23 for an adult ticket (we decided it was a little too touristy and that we would decline and age gracefully).

Is it Cheaper to Book Through My Hotel?

Many hotels are incentivized to promote trolley tours (in the same way that I receive a small commission if you book a tour from this page). While it is often slightly cheaper to book directly on the website, sometimes the cancellation policy is more flexible when booked in advance through a 3rd party such as Viator. The flip side is that hotels can quickly process an order and print tickets. Keep the tickets handy along the way.

Our Favorite Stops on the Old Town Trolley

Based on our experience so far, San Diego ranks as our favorite tour. Driving between the 11 stops included an expansive view driving over the Coronado Bridge. For the best experience with the Old Town Trolley in San Diego, plan to spend all day exploring. Balboa Park by itself could be an all day activity with over a dozen museums, gardens, and the San Diego Zoo!

We hopped on at Stop 11, Little Italy, worth a stop for lunch and a stroll. From there, the trolley returns to Stop 1—the Old Town Market—with cute but touristy shops and some photo opportunities. Stop 2 on the waterfront, is home to the Maritime Museum and Star of India. My favorite stop was Coronado (Stop 9), where we enjoyed lunch and a walk on the beach at the Hotel del Coronado. On the way we passed the Gaslamp Quarter (Stop 6), with a mix of restaurants for every taste.

The 90-minute St. Augustine Old Town Trolley offers riders 22 stops to explore. I found many of them clustered close together, while some like Stop 22 and the Fountain of Youth, were a bit touristy for our taste. Stop 8 leads to a beautiful church which is free to enter. We spent an hour touring Castillo de San Marcos National Monument (Stop 17), which requires a National Park pass or payment of the entrance fee.

The Lightner Museum (home to the former Alcazar hotel) is also popular, but easily accessible from the historic downtown area. You can also take the trolley for an afternoon of tasting at St. Augustine Distillery and San Sebastian Winery.

The 13 stops on the popular Old Town Trolley Tour in Key West, Florida span from Mallory Square to the West Lighthouse. Of course, we had to jump off at Stop 11 to take the iconic photo at the Southernmost point. (Note: there is renovation work happening through 2026 at the original site so for now, visit the replica at 1499 Duval Street.)

The first stop at Mallory Square includes the Key West Aquarium, on our list of top things to do in the Florida Keys with teens. The East Martello Fort at Stop 9 is home to Robert the Doll, visit if you dare! Smathers Beach is also located at Stop 9. Stop 12 is also popular with the Ernest Hemingway House and the Key West Lighthouse.

If you read this far, you now have enough information to make an informed decision about whether the Old Town Trolley Tour is right for you!