If you’re planning a visit to America’s oldest city, chances are, you’re already putting together an itinerary. Chances are that Castillo de San Marcos, the Colonial Quarter and the Lightner Museum are all on your must-see list — as well they should be! But if your tatses trend more toward off-the-beaten-path activities; i.e., attractions that are a little more on the unusual side? Then you’ll want to check out these St. Augustine, FL hidden gems.

Medieval Torture Museum

Although it’s not exactly family-friendly, those who aren’t faint of heart may want to pay a visit to the Medieval Torture Museum — St. Augustine’s most notoriously ghoulish gallery. Inside, the morbidly curious will discover a variety of exhibits detailing some of the most chilling examples of cruel treatment humankind has ever devised. It’s certainly not for the squeamish, but history buffs will no doubt find it a fascinating excursion.   

100 St George St, St. Augustine, FL 32084

Oldest Wooden Schoolhouse

Also known locally as the Juan Genopoly House, the Oldest Wooden Schoolhouse dates back to at least 1740. It has served many roles over the years — including family home and small-plot farm — but its most famous use was as a one-room schoolhouse in the 1800s. Today, the structure exists as one of the oldest buildings in the United States, even surviving a devastating 1702 fire that claimed countless other buildings in town.   

14 St. George Street, St. Augustine, FL, 32084

Fort Matanzas National Monument

While the famous Castillo de San Marcos is on everyone’s St. Augustine “must visit” list, we’d encourage visitors not to overlook the equally impressive Fort Matanzas, just a bit further south along the Atlantic coast. Fort Matanzas was completed in 1742, and was constructed of the same coquina (fossilized seashell) stone as the Castillo. This resulted in both buildings being so sturdy, they have survived multiple sieges and still stand today.  

8635 A1A S, St. Augustine, FL 32080

The Tin Pickle

If the St. Augustine Lighthouse & Maritime Museum is on your itinerary — and it should be! — then you’ll want to build in some extra time to stop at the Tin Pickle. The museum’s on-site snack bar is easy to miss if you don’t know it’s there. But once you sample their fudge, fresh-baked muffins and specialty hot dogs (featuring an ever-rotating selection of styles like Greek, Polynesian and the infamous Destroyer), you’ll be glad you stopped.   

100 Red Cox Dr, St. Augustine, FL 32080

Villa Zorayda Museum

This below-the-radar 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. 

83 King St, St. Augustine Florida 32084

Discover a Love Tree

“Love Trees” may not be unique to St. Augustine, but they’ve certainly carved out a space within the local imagination. Formed when two trees (usually of different species) grow together so closely that they become intertwined and impossible to separate, Love Trees are seen as symbols of everlasting togetherness. Legend has it that a kiss shared beneath a Love Tree will seal a heartfelt bond forever. If you’d like to find out for yourself, there are countless examples around town, with the most famous (a hybrid oak/palm) found at 6 Cordova Street.