Explore the History of the Nation's Oldest City

Welcome to where it all started. In the nation’s oldest city, history is everywhere you look.

October 25, 2021
walkway up to st augustine oldest schoolhouse

Day One

For a truly immersive experience, why not start by waking up in the historic district? The St. George Inn couldn’t bring you any closer to the time when the Spanish ruled Florida. Situated right across the street from The Castillo de San Marcos National Monument, this charming inn offers a bird’s eye view of the majestic fort from your balcony as you enjoy your breakfast.

Walk along the bayfront and you’ll come upon The Colonial Quarter. It’s hard to believe that there are 2 acres inside that immerse you in three centuries of Spanish colonial life and brief British occupation. Reenactors conduct musket firings and demonstrate various daily activities such as blacksmithing in authentic historic surroundings. Be sure to stop by the Taberna del Caballo for some sangria and an afternoon rest under a vine covered pergola.

the luxurious patio of the Columbia St. Augustine
Columbia Restaurant

Back on St. George Street, the Oldest Wooden School House welcomes you with its beautiful secret garden. Inside this historic museum you’ll be transported to school life in the 1700s with original antique furnishings and rare artifacts. In the evening, follow your nose to Columbia Restaurant, one of Florida’s oldest family-run restaurants serving authentic Spanish and Cuban cuisine. Be sure to try their famous “1905 Salad” and black bean soup. They’re classics.

Day Two

Wake up to a hearty breakfast as this local fav, the Blue Hen. Fluffy Southern biscuits with peach butter or honey and a cup o’ joe might be all you need. But if you’re needing a bit more, the pumpkin pancakes are sure to fill you up.

Foot Soldiers Monument, part of Black History in America's Oldest City.
St. Augustine Foot Soldiers Monument

Now you’re ready to explore the area known as Lincolnville. This neighborhood was founded by newly-freed slaves after the Civil War. A visit to the Lincolnville Museum & Cultural Center takes the visitor back 450 years to the beginnings of Black history in the Ancient City. The ACCORD Freedom Trail takes visitors on a journey to 31 markers at historic sites that played an integral part in Black history during the Civil Rights movement in the 1960’s.

Of course, the history of St. Augustine changed course with the arrival of Henry Flagler, who launched tourism in Florida when he built his Hotel Ponce de Leon and ushered in the Gilded Age in the state. You can still get a feel for the extravagance and opulence of the time through Historic Tours of Flagler College, where you’ll be blown away by the Spanish Renaissance architecture, the intricate mosaic tile floors, the majestic painted ceilings in the dining hall surrounded by the largest collection of Tiffany stained glass windows anywhere. Whew! You might need a break.

Interior of the historic Ice Plant Bar, located in Historic St. Augustine.
The Ice Plant

That takes us to the St. Augustine Distillery, housed in a historic ice-manufacturing plant from the 1920’s. Watch their spirits made from scratch from locally-sourced ingredients, then have a free tasting of their award-winning spirits. Right next door is the iconic Ice Plant Bar & Restaurant, the perfect place to immerse yourself in early 20th century history with hand-crafted cocktails and farm-to-table cuisine. You might want to walk it off with a short stroll down to Aviles Street, the oldest street in the country. Along its brick-lined street of quaint shops and galleries you’ll come upon Peace Pie, home of the ultimate ice cream sandwich made with a layer of pie filling. Stick a fork in it, you’re done!