Exploring St. Augustine, Florida – America’s Oldest City
- Gail McElroy
- Sep 22, 2022
- 4 min read
On a recent road trip through America’s southeast states, we visited St. Augustine, Florida, the oldest city in the United States. Located on the northeast coast of Florida just below Jacksonville (the closest major airport), St. Augustine makes for a great launching point for exploring Florida’s Atlantic coast.
Founded in 1565 by Spanish explorers, St. Augustine is the oldest continuously inhabited European-established settlement in the contiguous United States. While rich in history with some beautiful architecture, the city is mostly full of touristy shops and restaurants, which was a little disappointing to us.
My research promised a quaint town full of Spanish history and architecture. In reality, there is a one-block section of “old town” that houses Flagler College (formerly the Ponce de Leon Hotel built in 1888) on one side of King Street and the Lightner Museum (formerly Hotel Alcatraz) on the other. These Gilded-Age buildings, both once luxury hotel resorts commissioned by railroad magnate Henry Flagler, are featured in the photos that dominate all the tourism websites and books for St. Augustine. Both properties are architectural marvels worth checking out.
Driving in from Savannah, Georgia, we arrived in St. Augustine mid-morning and began our day by exploring this historic block. Then, we walked along King Street to reach the Bridge of Lions, an historic drawbridge with lion statues that crosses over the Matanzas River and leads to Anastasia State Park and Crescent Beach. The bridge is particularly beautiful and photogenic at sunset when the pink hues cast a magical light on the bridge and boardwalk. (For the best shot, cross the bridge and look back at St. Augustine.)
We had lunch at Casa Reina located in an historic building across the street from the Bridge of Lions. The Mexican taqueria serves diverse and delicious dishes. Once fortified and rehydrated, we walked along Aviles Street (which is really more like an alley) to check out a couple of museums.
On the way back to our hotel, we happened on to a "love tree" - a palm growing out of an oak. According to local lore, if you kiss under a love tree you will have everlasting love.
We stayed at The Collector Luxury Inn & Gardens, a charming adults-only property with a collection of nine individual historic houses that have been refurbished into hotel suites. The inn’s website describes the property as: “Part contemporary hotel, part friendly B & B . . . wrapped up in a storied landmark that inspired some of history’s most admired thinkers, including Abraham Lincoln, Mark Twain and Sinclair Lewis.”
At check-in, guests are given reusable water bottles to fill at the beverage station located off the lobby, which features coffee, tea and flavored water. In this same area, guests have access to snacks in the afternoon and a European-style continental breakfast each morning.
The valet assists guests with luggage and provides a tour of the property on the way to your room. Amenities include a heated pool, fire pits, water fountains and features, and seating along garden pathways and courtyards. Guests may also borrow bicycles to ride around town and check out lawn games to play.
Adjacent to the pool is a quaint on-site bar, The Well, housed in a small stone building where guests may enjoy afternoon and late evening cocktails. The inn is a wonderful oasis to escape the bustle of touristy St. George’s Street, as well as take a break from exploring the historic gems located throughout America’s oldest city. (We were disappointed we didn’t book an additional night to truly take advantage of all the property had to offer.)
After resting, we headed back out to do some more exploring, this time taking our car. We stopped at the Castillo de San Marcos National Monument, the oldest masonry fortification in the continental United States built by the Spanish in 1695 to defend Florida and the Atlantic trade route. Visitors can walk along the walls for some of the best views in the city.
St. Augustine has a ton of restaurants to choose from – all of them are busy and most require reservations. We chose the funky Floridian for dinner, which offers a fresh spin on traditional southern cooking. The menu changes seasonally and depends on availability of locally sourced food. We chose two local specials that were as delicious as promised. Too full for dessert, we paid our bill and “waddled” back to our car. (Parking tip: The lot in front of the restaurant is always full and hard to find a spot. When we called to make a reservation, the hostess told us about parking behind the restaurant. The lot says “permits only” for businesses open during the day, but they don’t check at night. It was the hot ticket since the lot was virtually vacant.)
The next morning, we headed out for our next destination of Ft. Lauderdale. We squeezed in the things we wanted to see during our 24 hours in St. Augustine, but two nights and days would have been preferrable. The history of America’s oldest city makes it worth visiting if you are in the area.
If you have kids be sure to visit these interactive sites:
For the "kids" over 21, check out St. Augustine Distillery.
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