Many cities have a historic district. Even so, we’re of the opinion that Old Town St Augustine is on another level entirely. After all, St. Augustine is the nation’s oldest city, dating back to the mid-1500s. We just have so much more history to draw from. 

With that in mind, let’s take a look at some of the best things to do and see in St. Augustine’s Old Town.

Take a Trolley Tour

There’s so much to experience in Old Town, it might be a good idea to start with a guided tour. That way, you can take note of which stops you’d like to make when exploring on your own. Old Town Trolley Tours offers upbeat sightseeing tours of some of Old Town’s most popular stops. Single day and multi-day passes allow for hopping on and off the trolley as often as you like. So you always have the option to stick around for the whole spin, or stop at whatever strikes your fancy and pick up where you left off later.

Check Out a Vintage Lockup

Built in 1891, the Old Jail served as St. Augustine’s primary correctional facility until 1953. Since being taken out of active duty, the jail now offers visitors a fun and unique attraction. Guests can learn fascinating facts about the historic importance of the jail, as well as the various purposes for which its been used over the last century and a half. Tour the jail cells, check out period clothing and tools, and hear intriguing stories about some of the ne’er-do-wells who passed through its confines. Tours are offered every 20 minutes, 364 days per year (excluding Christmas Day).

Experience the Fountain of Youth

Does the Fountain of Youth really exist? Spanish explorer Ponce de León was convinced of it. He was also fairly certain it was here in Florida. And while actual magical waters that wash away the years may be a myth, St. Augustine visitors can nonetheless visit the Fountain of Youth Archaeological Park, where they’ll find an abundance of fascinating history on the early Spanish settlers who first landed in the area in 1565. Of course, you’re also welcome to sample the waters from the famous spring that de León was so certain could turn back the clock. 

Go Back in Time at the Colonial Quarter 

In many ways, St. Augustine’s Colonial Quarter is the heart of Old Town. Colonial Quarter is an interactive outdoor complex that offers a living history of the Spanish and English settlers that helped establish St. Augustine more than 450 years ago. Historical reenactors provide up-close demonstrations of early American skills like blacksmithing and ship construction. The scalable watchtower offers intrepid adventurers a panoramic view of the quarter and its surrounding area, as well as the nearby Castillo de San Marcos. A restaurant, pub, and gift shop are also on hand for refreshments and entertainment.

Stroll St. George Street 

The charming St. George Street is Old Town’s liveliest thoroughfare. A pedestrian-only walkway, St. George Street encourages leisurely exploration. Many incredible points of interest dot its length, including the stately Old City Gate, the city’s Oldest Wooden Schoolhouse, and the historic Pena Peck House, which served as a transitional residence for many of the area’s early international dignitaries. This is also where you’ll find the Medieval Torture Museum, the starting point for many of the city’s famous ghost tours, and scores of unique shops and boutiques.

Visit the Villa Zorayda Museum

This hidden-gem exhibit hall has fascinated visitors for generations. Inside you’ll find a quirky and diverse mix of gilded-age Victorian antiquities, curiosities, and other objets d’art. Ceramics, artisanal furniture, sculptures, and other surprises await around every delightful corner. The building itself is even a creative masterpiece, featuring intricate wooden scrollwork, hand-carved inlays, and gorgeous imported floor tiles. Villa Zorayda is such an impressive and unique attraction that it’s listed on the U.S. National Register of Historic Places.