48 Hours of History and Adventure in St. Augustine and Florida’s Historic Coast

St. Augustine is the oldest continuously occupied European city in United States. America’s oldest city is filled with fascinating history and some surprises, especially in the culinary and art scenes. Here’s how to spend 48 hours along Florida’s Historic Coast combining a beach stay with plenty of history, food, and adventure.

On Aviles Street, the Oldest Street in America

Where Ponce de León First Saw La Florida

It’s fitting for the first stop along Florida’s Historic Coast to be the place where Juan Ponce de León first spotted La Florida and claim it for Spain. The Guana Tolomato Matanzas National Estuarine Resarch Reserve, or more commonly called GTM Reserve, is that place. The reserve covering over 76,000 acres of conservation land from Ponte Vedra Beach to Palm Coast, is also where the the 30°8’ N latitude is located that’s believed to be the location where Ponce de León calculated his fleet position in 1513. You’ll find the historical marker and a statue of Ponce de León just south of Ponte Vedra in the GTM Reserve North Beach Access Parking Lot on the west side of A1A. Take the crosswalk to the boardwalk running through 30-40 foot sand dunes, some of the tallest dunes in Florida. My friend Adeina and I took in the view from the beach, but not for long as the weather was taking a turn. We were supposed to go shark tooth hunting (yes, that’s a thing on Florida’s Historic Coast) and look for shells, but the weather altered our plans. I thought the wind picking up the sand and waves increasingly getting more turmultous added a little ambiance as I imagine what it must have been like for Ponce de León to see this stretch of coastline. Before heading back to the car, I climbed the steps up to an overlook perched on top of the dunes. The 360° view is incredible from that vantage point.

Lunch at Aunt Kate‘s

As we walked up to Aunt Kate’s in a grove of live oaks on the bank of the Tolomato River, I knew this southern gal was in for a real treat for lunch. Aunt Kate’s has been serving up local seafood for over 120 years and it’s reminiscent of the kind of places I went as a child when my family went on beach vacations. In 1900, Frank and Catherine Usina prepared roasted local oysters for Standard Oil and Railroad magnet Henry Flagler and his friends. That started the tradition of serving seafood continuously from this spot. The restaurant is called “Aunt Kate’s” because that’s what extended family called Catherine Usina. You not only get fresh local seafood here, you also get a taste of St. Augustine’s Menorcan culture as Frank Usina’s family were indentured servants from the island of Menorca who fled to St. Augustine from the failed English Colony at New Smyrna in 1768. This is a spot you want to go hungry to and say YES to the bread basket filled with moist pumpkin bread, slightly spicy cornbread made with a Menorcan spice, and Johnny cakes made with applesauce and cornmeal. Order the fried green tomatoes served with a key lime sauce as your starter. They’re scrumptious. I went for the St. Augustine Style Shrimp. It’s a dozen shrimp fried, grilled, boiled, or blackened and served with your choice of two sides. I opted for pickled beets and cheese grits. The collard greens are made with Menorcan spice vinegar. They looked phenomenal, but I don’t eat bacon. Somehow we saved a little room for dessert. It was a toss up between the key lime pie and peach cobbler. Since it was cool and windy, we went for the warm peach cobbler topped with vanilla ice cream dusted with cinnamon.

From the restaurant and pier, you have an excellent view of Fort Mose. Established in 1738, Fort Mose was the first legally sanctioned free black town in the United States. It is a National Historic Landmark, a historic state park, and part of the UNESCO Slave Route Project.

Stay in Vilano Beach

Before heading into Old Town, we checked into Holiday Inn Express Vilano Beach. The quaint beach town is the closest beach town to downtown St. Augustine and just a couple of minutes from Old Town. It’s a great way to combine a beach stay while you explore the history and food of America’s oldest city. I found my spacious and colorful room to be quite comfortable. It has a coffee area, mini fridge, microwave, and desk area. I particularly liked the built in bench to put suitcases and the large bathroom. My room also had a balcony, which I would have enjoyed if the weather would have been a little better. Breakfast also comes with your room at the Holiday Inn Express. There’s also a local coffee shop connected to it. Plus, the staff is ultra friendly and helpful. The hotel is a couple of blocks from the beach. It’s a less than 5 minute leisurely stroll to the sand.

Castillo de San Marcos National Monument

Founded in 1565, Saint Augustine is the nations oldest city. A great way to explore it is by jumping on an Old Town Trolley. One of the stops and one of the main attractions in St. Augustine is Castillo de San Marcos National Monument.

Strolling Through Old Town

We took a late afternoon stroll through Old Town checking out the many shops, restuarants, and watering holes. We even found a spot where you can become a pirate and I gave it my best “Aaarrgggghhhh.” The Cathedral Basilica of Saint Augustine was closed for the day but we still took a few moment to admire the oldest Catholic parish within the present day United States. It was founded on September 8, 1565. While we were there one of the green Old Town Trolley Tours rolled by. The hop on and off open-air trolley is a great way to see 22 stops in the city.

Dinner at Catch 27

Catch 27 is a fabulous dining experience in the heart of Old Town. Adeina and I met a friend there for a scrumptious dinner in their delightful back garden. I tried one of their speciality cocktails. The Due East is made with St. Augustine Distillery vodka, preserved lemon, Aperol, orgeat (syrup made from almonds, sugar, and rose or orange flower water), and orange blossom. The refreshing cocktail was perfect for relaxed elegance of Catch 27, which is a nod to Florida being the 27th state on March 3, 1845. Catch 27 specializes in seafood with a distinct Southern twist. We decided to eat light and order several appetizers followed by soup or salad. The deviled eggs with southern fried oysters are a must. We opted to get the house made tomato-bacon jam on the side. The deviled eggs topped with crispy corn-fried oysters are so good we ordered a second helping. The also had the warm pimento cheese crab dip served with crostini. I consider myself a deviled egg and pimento cheese aficionado and this dip was out of sight. Even if you’re not a pimento cheese fan, order the dip. We also had the smoked salmon spread served with house made potato chips and dill pickle tarter sauce. It’s also delicious. Instead of soup I decided to nosh on the shaved pear and blue cheese salad with field greens, dried cherries, and spiced pecans with lemon honey vinaigrette on the side. Since we dined on the lighter side, we splurged for dessert and tried the coconut key lime panna cotta with graham cracker crumble and strawberry jam. The light and creamy dessert as a twist on the classic key lime pie was a perfect way to end a great day in St. Augustine.

Live TV and Tour of Hyatt Place

The next day we woke up to rain and I have several live television segments so we didn’t venture out much. In every vacation or trip, it’s always a good idea to add in at least one opportunity for some down town to sleep in, do a little work, or simply relax and enjoy coffee before going 100% into explorer mode as we would do for the afternoon and evening. It was also a chance for us to tour a couple of room in the new Hyatt Place St. Augustine/Vilano Beach. This is not your typical Hyatt Place. It’s an elevated experience. We toured one of 4 corner suites and a spacious regular room. The 120-room Hyatt Place is across the street from the Holiday Inn Express. Both are affordable options close to the beach and to Old Town. For high-end luxury, Ponte Vedra has multiple 4-star+ options. If a quaint, beachy town is more your vibe, Vilano Beach is perfect.

Lunch at Pesca Rooftop

With the rain moving out, we headed up to Pesca, the rooftop bar at Hyatt Place. They serve refined small-plate fare blending southern coastal cuisine with a Mediterranean flair, which was perfect for our desire to have a light lunch. We ordered the colorful Mediterranean mezze with hummus, pan roasted olives and goat cheese, yuca croquettes (yuca and cheese fritters), and bacalaitos (flat crispy salt cod fritters). All were delicious.

More Exploring of Old Town

There are so many interesting historic buildings, homes, and sites in Old Town it’s impossible to see it all in just one walk around town so we headed back over to wander around town. We found a parking spot near the cathedral and lucky for us it was open and we were able to take in a moment of prayer and peace in its beautiful sanctuary. Next we stopped in Relámpago Coffee Lab for an afternoon coffee and enjoyed the pick-me-up on their porch. We just made it in time to tour Memorial Presbyterian Church. Self-guided tours are available Friday 11 AM to 3:30 PM and Sundays 12:15 PM to 3:30 PM. It is gorgeous inside, but the 1890 church is arguably the most magnificant building in St. Augustine with its striking architecture. The lure of a sweet treat and bubbles drew us into Choco-Lattes where we sipped Prosecco while splitting a matcha crinkle cookie before heading off to the distillery tour.

Sipping Whiskey at St. Augustine Distillery

Housed in Florida’s oldest ice plant, St. Augustine Distillery uses local ingredients to produce Florida’s most awarded spirits. They make vodka, gin, and rum, but their specialty is bourbon. Their tour is different from other distilleries. The free self guided experience has tour guides stationed along the journey teaching you how to make their four signature cocktails. The first stop is to sample a Florida mule, their twist on a Moscow mule. Their vodka is made from sugarcane, differing from traditional vodka made from potatoes or corn. It is a little bit sweeter than traditional vodka. We went on to check out the barrels, stills, and fermenting “sweet mash” tanks before sampling their award-winning bourbon. I was given a great tip to tasting bourbon. Take the first nose-flaring sip then judge the bourbon in your second sip. There’s so much of a difference between the sips and gave me a new appreciate for the spirit. The distillery is a popular spot getting over 165,000 visitors a year for over 2 million visitors in a decade. Saturdays are busiest with over 1300 people passing through. Spend some time perusing the shop for mixers, bar ware, apparel, and more including the cocktail boxes with everything you need to make their signature cocktails.

Lively Tunes and It’s in the Cards

As we walked from the distillery to dinner we past a couple of fun spots. The first was a gathering of folks listening to live music. The second was The Seventh Root where I got my tarot cards read and got to hang with Captain Petey the cute rescue pooch.

Dinner at Bourbon and Boards

We went to Ancient City Bourbon and Boards for dinner. It’s the hottest new restaurant in St. Augustine. For a cocktail I debated between the Mercy Mercy Me or Butterfly Sugar. As part of a tasting experience for their new spring menu, I sampled both and preferred the Mercy, Mercy Me made with Santo mezquila, orange liqueur, lime, orange, and prickly pear. We also tasted the scallops served over lemon risotto with mushrooms and tarragon along with crispy artichoke parts tossed in serrano aioli and topped with a sun-dried tomato and sweet onion confiture and crispy kale. I politely scarfed down the delicious dish. For dessert we split the decadent and gluten-free chocolate tort with white chocolate cashew ganache and orange crisp. With their elaborate boards and creative cocktails, this is also a wonderful spot for weekend brunch.

Art Walk on Aviles

After dinner we strolled down Aviles, the oldest street in the Continental United States. Originally it was known as the “street of the Royal Hospital.“ It was renamed in 1923 in honor of the birthplace of Pedro Menendez de Aviles, the founder of Saint Augustine, Florida. It’s a lively street lined with shops, eateries with outdoor seating, and a thriving art scene. We stopped in The Bart gallery to admire the works of 18 different artist while sipping a glass of wine. As soon as we walked in we were oven a pair of ChromaDesign glasses that give a 3D effect with pops of color in some of the art. With comments like, “Anything I do in my life I go all in baby,” chatting with the energetic and eccentric co-owner Philip was a hoot!

Sunrise Stroll on Vilano Beach

The next morning I went for a sunrise walk on the beach. It was foggy and misty making for a beautifully not perfect start to a Saturday that was perfect for a few moments of reflection while walking.

Dolphin and Wildlife Tour with Florida Water Tours

A cloudy morning was perfect for a Dolphin and Wildlife Adventure with Florida Water Tours. A portion of every Florida water tours to get goes directly to Florida Water Warriors, which is an eco-education organization. With Captain Kevin at the helm and his brother Mike sharing his knowledge of the wildlife and history of the area, we headed out on the 40-foot pontoon boat Osprey. We quickly spotted some double crested cormorants, pelicans, and ospreys. We past Vilano Beach to an estuary, where the river meets the sea, teaming with wildlife. As we passed Anastasia State Park, we saw dolphins and spotted a few turtles. I really enjoyed seeing Castillo de San Marcos and Old Town from thewater before we cruised back to the marina. This 1.5-hour adventure is fabulous for families and anyone who enjoys a sightseeing by boat experience. They also Brunch & Bottlenose Cruises, Sunset Cruises, and Wine Tasting Cruises.

Brunch at Odd Birds Cafe

We didn’t go far fro brunch. The Odd Birds Cafe has the look of a locals’ favorite kind of place. They serve a variety of Venezuelan classics along with American breakfast classics. I went for the grits bowl with stone ground grits, chihuahua cheese, scrambled egg, and diced scallions. It was perfectly filling. You can also get it with bacon.

Fort Matanzas National Monument

Last stop in St. Augustine was Fort Matanzas National Monument about 15 minutes south of Old Town. In addition to the fortified coquina watertower completed in 1742 to protect the Spanish military settlement of St. Augustine, there are two trails to explore the nature side of Fort Matanzas. One trail is a quarter of a mile round-trip it takes you to a small beach area with a view of the fort. The other trail is the Coastal Hammock Trail. It’s a lollipop loop that goes along boardwalks through the dense coastal forest with views of live oaks and other vegetation, along with a spot looking out at dunes. I walked both trails while waiting to take the free ferry to the fort. Passes for ferries are given out on a first come, first served day of basis. You can’t reserve seats in advance. We were about to get on the 3:30p ferry with Ranger Caroline and Captain Ranger Patrick. In a couple of minutes we were at Fort Matanzas. We were greated by a ranger dressed in a British soldier costume because they were doing special candlelight tours that evening. On average six soldiers lived in the quarters on the first floor for 30 days and an officer stayed in the room on the second floor. I climbed the ladder to top of the fort to take in the view ending a fun adventure of history, food, and outdoors in the nation’s oldest city.