St. Augustine, Florida is about a 2 and a half hour drive from Walt Disney World, but here you can find real-life haunted mansions, pirate ships, and much old world charm. I am lucky enough to only live a half an hour away, but yet, I feel transported to a time filled with treasure maps and swashbucklers. I recently took a trolley tour of the “Ancient City,” and wanted to share with all of our readers what a gem of a city St. Augustine is!
Trolley Tours
St. Augustine is a pretty compact city and could be explored on foot, but I would suggest a trolley tour in order to see the sights and hear the rich history of the city that dates back to the 1600s. There are a few different companies that offer tours of the city. All will highlight the historic landmarks of the city, while giving visitors facts and stories about the sights. Most of the tours have stops located around the city where guests can get on and off to wander around and visit the attractions in the different areas of the city. I like hopping on and off at my leisure, and using the trolley to cut down on the amount of walking.

Trolley Ride in St. Augustine, Florida
During the Christmas holiday is a particularly special time to visit. Old Town Trolley Tours offers the “Holly Jolly Trolley Ride,” and visitors are taken on a tour of St. Augustine’s businesses lit up with lights. My family and I had a joyful time seeing the Christmas lights while singing carols throughout the ride. After riding, guests are given sugar cookies and warm apple cider, and Santa Claus is on hand for little ones to relay their Christmas wishes.

Riding the Holly Jolly Trolley

Downtown St. Augustine at Christmastime
DIStracted Tip: Many of the trolley companies will offer discounted tickets to customers who purchase their tickets online.
Attractions
Dubbed the “Oldest City in the United States,” St. Augustine has many different historical attractions for visitors to see. Perhaps the most famous is Castillo de San Marcos, the oldest masonry fort in the continental United States. Visitors can explore the old fort unguided, and discover what life was like for the soldiers who were stationed there. The sprawling lawn located behind the fort is a great place to have a picnic lunch, or just to sit and rest on a beautiful Florida day. Castillo de San Marcos is also said to be inhabited by many spirits of those who once lived there. The fort has been featured on ghost hunting television shows, and therefore is a popular spot for for guests to test out their amateur ghost hunting skills.
- Top of Castillo de San Marcos
- Cannons at Castillo de San Marcos
- Castillo de San Marcos
- St. Augustine Lighthouse
- Fountain of Youth
- Fountain of Youth
- historic cemetery
- The Black Raven Pirate Ship
- Oldest Wooden Schoolhouse
- Oldest House
- Lightner Museum lit up for Christmas
If you have an aspiring pirate in your midst, then I suggest boarding The Black Raven Pirate Ship, and batten down the hatches for a battle of epic proportions! The Black Raven crew takes landlubbers out to sea in battle to get back their stolen treasure. Once the treasure is returned, mateys are brought safely back to shore.
Museums
The Oldest Wooden School House, Oldest Store and Jail, and the Oldest House are also located in St. Augustine. These locations are now museums. At many of these locations actors are dressed as characters from the time period and share stories of life in the 1600s. Guests can sip from the Fountain of Youth, and hope to stay young forever. The Lightner Museum and Flagler College located in the downtown area are also beautiful buildings open to tourists.
A short drive from downtown is the St. Augustine Lighthouse Museum. One of my “Bucket List” goals is to visit all of the lighthouses on the coast of the Eastern United States. The Lighthouse in St. Augustine is beautiful! Visitors are allowed to climb the spiral staircase all the way to the top. My husband took me on a special nighttime, Friday the 13th tour. We toured the lighthouse and the keeper’s house located next door. We were able to hear all of the ghost stories and paranormal experiences of the employees.
Dining
St. Augustine boasts many different restaurants in its downtown area ranging from casual to elegant. My favorite is Mojo Old City BBQ! The food is delicious, and there is outdoor seating on the patio. Other recommendations for the area include: A1A Aleworks; a microbrewery, Ice Plant, Columbia Restaurant, and Harry’s Seafood Bar and Grill. St. George Street is the location of many restaurants in the city; if you’re not sure what you are in the mood for, take a stroll there, because I have not found a restaurant in St. Augustine that I did not like.

A1A Aleworks Restaurant
If you are hankering for something sweet, then there are many places to satisfy a sugary craving! Ben and Jerry’s just opened up a shop on St. George Street. I also suggest Kilwin’s for fudge, and Savannah Sweets to pick up a praline. Disney fans will appreciate indulging in the ever popular Dole Whip, even while visiting St. Augustine!

DOLE WHIP!!!
If chocolate is your passion, like me, then I highly suggest a visit to the Whetstone Chocolate Factory for a tour. The factory opens its doors to visitors wishing to see (and taste) their chocolate making process! I took this tour last summer with my daughters, and had a fun day tasting the different chocolates created at the factory.

Whetstone Chocolate factory tour

Enjoying chocolate samples
Shopping
Along with restaurants, St. George Street is also home to many different shops. There are many “tourist-y” shops that feature St. Augustine merchandise for those that love t-shirts, magnets, or other knick-knacks that note they’ve visited a particular place. There are also specialty stores, such as a magic shop where one can take in a free magic show during the day. Many of the shops along St. George Street are open-air. One of my favorite shops is one that sells Spanish-style clay pots and tiles. On my last visit, I noticed that more upscale stores are coming in, which is great!

Shopping for Spanish-style Clay Pots
St. Augustine is a lovely place to visit; full of historic landmarks, and the interesting stories that go along with them. No matter your interests, there is something everyone will enjoy there. I suggest making “The Ancient City” a stop during your travels to or from Walt Disney World Resort. It’s worth a day’s visit!
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