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St. Augustine is considered the oldest city in the USA, and its rich history makes it one of Florida’s most fascinating vacation destinations. There are many popular historic sites to explore, such as The Fountain of Youth, St. Augustine Lighthouse & Maritime Museum, and the Colonial Quarter, but for those who prefer to wander off the beaten path, there are also plenty of lesser-known attractions to discover.
If you want to beat the crowds and see some of this old city’s more eclectic sights, be sure to add some of these 14 hidden gems to your St. Augustine sightseeing itinerary.
1. Aviles Street
Tourists tend to flock to St. George Street, which is the heart of historic Downtown St. Augustine. But it’s not the only place to get a taste of the city’s history!
Aviles Street, just a few minutes away on foot, is considered the oldest public street in America because it appears on maps that date back as far as the 1570s. Wander down this cobblestone street to appreciate its heritage buildings, browse its independent boutiques and art galleries, and grab a bite to eat from one of the many fantastic restaurants that operate here.
2. Ice Plant Bar
- Website: iceplantbar.com
- Address: 110 Riberia St, St. Augustine, FL
The award-winning St. Augustine Distillery operates in a former ice plant, and its on-site bar is the perfect place to sample a few of its tasty spirits. Expert mixologists craft delicious cocktails carefully to deliver unique flavor profiles you won’t find anywhere else.
The fresh fruit juices used in the cocktails are made in-house, and there are low- and no-alcohol cocktails on offer for those who don’t drink. Brunch, lunch, and dinner menus are also available if you want to enjoy a bite to eat while surrounded by the unique historic architecture of the 1920s building.
3. The Love Tree
Address: 6 Cordova St, St. Augustine, FL
Love trees are two different species of tree that grow in, on, or around each other so tightly that they will both die if they are separated. It’s thought that they symbolize the everlasting strength of two lovers, and legend has it that kissing beneath a love tree will seal a couple’s love for eternity.
St. Augustine is already considered a romantic city thanks to its beauty and charming atmosphere, so if you’re visiting with that special someone, be sure to look out for one of the city’s numerous love trees. The most renowned is on Cordova Street, where a sabal palm grows from the heart of a grand old oak.
4. Villa Zorayda Museum
- Website: villazorayda.com
- Address: 83 King St, St. Augustine, FL
Wealthy hardware merchant and architect Franklin W. Smith built Villa Zorayda in 1883 to serve as his winter home. The beautiful Moorish Revival building is typical of Smith who traveled the world to study ancient civilizations’ design, architecture, and construction methods.
The Villa Zoradaya Museum is strongly influenced by Spain’s Alhambra Palace, and it’s made all the more spectacular by the eclectic collection of treasures inside, including the world’s oldest carpet made from the hair of ancient Egyptian cats.
5. The Dungeon Under the Stairs of the Oldest Wooden Schoolhouse
- Website: oldestwoodenschoolhouse.com
- Address: 20-30 St George St, Augustine, FL
The Oldest Wooden Schoolhouse is a fascinating attraction that offers a glimpse into school life in the 1700s. One of its lesser-known and most creepy features is the dungeon under the stairs where misbehaving students used to be locked up. The Schoolhouse lies in the Historic District near several other popular attractions, including Potter’s Wax Museum and the Colonial Quarter.
6. Crescent Beach
Crescent Beach lies on the narrow southern portion of Anastasia Island and is a quieter alternative to the likes of St. Augustine Beach and Vilano Beach. This stretch of coastline is incredibly beautiful and relatively undisturbed, with just a handful of residential properties, vacation rentals, restaurants, and taverns.
The beach itself is wide and spacious, and there’s a beachfront park with excellent facilities, including car parking, restrooms, and picnic gazebos. It takes about 20 minutes to reach Crescent Beach by car from the Historic District, and the drive is definitely worth it for a peaceful beach day.
7. The Black Raven Pirate Ship
- Website: blackravenadventures.com
- Address: 111 Avenida Menendez, St. Augustine, FL
The Black Raven is a floating theater that delivers thrilling live, interactive pirate shows suitable for children and adults. There are three main voyages to choose from — the daytime Treasure Hunt Show, the evening Tropical Sunset Show, and the adults-only Rum Runners Show.
Be prepared for a sing-along with the crew as you admire the sights dotted along the Matanzas River. A journey on the Black Pirate is a great way to finish off a swashbuckling few hours at the St. Augustine Pirate & Treasure Museum which is just a 10-minute walk away.
8. The Secret Chamber in the Castillo de San Marcos
- Website: nps.gov/casa
- Address: 11 S Castillo Dr, St. Augustine, FL
Castillo de San Marcos is a Spanish Colonial fort built in 1672, and it’s one of the most popular attractions in the old town area. Its secret chamber lies deep inside the fort and was only discovered in 1833. It’s said that human skeletons were found inside, believed to be the bodies of two forbidden lovers.
The story goes that Colonel Garcia Marti and his young, beautiful wife Dolores arrived at Castillo de San Marcos in the late 1700s, only for Dolores to fall in love with the Colonel’s assistant, Captain Abela. Dolores and Captain Abela went missing one night, and the Colonel came up with convenient explanations for their whereabouts.
Decades later, the chamber was discovered along with its two skeletons. Many believe the chamber to be haunted; there are many reports of orbs, apparitions, and the mysterious smell of a woman’s perfume.
9. Cafe Alcazar
- Website: thealcazarcafe.com/cafe-alcazar
- Address: 25 Granada St, St. Augustine, FL
The Lightner Museum, housed inside the spectacular former Hotel Alcazar, is a popular St. Augustine attraction, but not everyone knows about its unique eatery. Cafe Alcazar is set inside what was once the world’s largest indoor swimming pool.
Enjoy a delicious meal surrounded by the opulent decor and with the charming soundtrack of a live guitarist or pianist. Don’t miss out on wandering around the museum’s courtyard after your meal, where there’s a pretty koi pond with a footbridge surrounded by lush foliage.
10. Treasury Street
Treasury Street is the narrowest street in the United States, having been built just wide enough for two men to transport a chest of gold from a docked ship to the treasury. Making the street as narrow as possible ensured that a horse-drawn carriage couldn’t ride past and snatch the gold.
11. Dolphin-Watching at Fort Matanzas
Address: 8635 A1A S, St. Augustine, FL
Fort Matanzas National Monument is an important attraction on Florida’s historic coast, but it’s also a haven for native flora and fauna. Although the likes of St. Augustine Alligator Farm Zoological Park and Anastasia State Park attract animal enthusiasts, Fort Matanzas is one of the best places in St. Augustine to spot wildlife.
More than 200 species of bird have been identified here, and eagle-eyed visitors might catch a glimpse of many tiny rodents such as short-tailed shrews, marsh rice rats, Florida mice, and cotton mice. When you look towards the waterways, you might spot bottlenose dolphins, West Indian manatees, North American river otters, and North Atlantic right whales.
12. Tiffany Stained Glass Windows at Flagler College
- Website: flagler.edu/where-history-begins
- Address: 74 King St, St. Augustine, FL
Flagler College is set inside the lavish former Ponce de Leon Hotel, which was commissioned by railroad magnate Henry Flagler in 1888. It’s a perfect example of Spanish Renaissance architecture and there are many fabulous design features to make note of, one of which is the windows in the college’s dining hall.
Sparkling sunlight shines through 79 ornate stained glass windows, which were designed by Louis Comfort Tiffany, son of Charles Lewis Tiffany, who founded the renowned luxury jewelry design house Tiffany & Co.
13. Nighttime Walking Ghost Tours
- Website: www.ghosttoursofstaugustine.net
- Address: 27 San Marco Ave, St. Augustine, FL
Given the sheer age of St. Augustine, it’s no surprise that it’s considered one of the most haunted American cities. There are many notoriously haunted locations, such as the old City Gates, the Old Jail Museum, and Tolomoto Cemetary, but one of the coolest ways to explore St. Augustine’s paranormal side is to take a lantern-lit walking ghost tour at night.
Professional guides have been running these tours for more than 30 years to showcase the ghostly goings-on in the city’s historic back alleys and hidden laneways. You’ll learn about some of the city’s notorious ghosts and the factual stories that pertain to them, which have been gleaned from extensive research conducted by passionate locals.
If you don’t fancy a walking ghost tour, consider the popular Ghosts & Gravestones Trolley Tour instead.
14. Spanish Military Hospital Museum
- Website: smhmuseum.com
- Address: 3 Aviles St, St. Augustine, FL
The Spanish Military Hospital Museum offers fascinating insights into the medical techniques used in Spanish Colonial times. The daily guided tours include performances from actors who demonstrate how surgeries were performed more than 400 years ago. You’ll also visit a replica apothecary and learn how medicines made with Colonial herbs laid the groundwork for some of today’s most popular modern medicines.
Explore St. Augustine’s Hidden Gems
Now you’re clued up on the best hidden gems and secret sights in St. Augustine, you can start planning your adventure in this captivating historic city. Where will your St. Augustine getaway take you?
