All Articles A sunny three-day weekend in St. Augustine, FL

A sunny three-day weekend in St. Augustine, FL

Jessica Serna shares her must-visits on a quick trip to one of the oldest cities in the U.S.

By Tommie Ethington4 Nov 2022 5 minutes read
Saint Augustine Lighthouse at Anastasia State Park in Florida
Saint Augustine Lighthouse, Anastasia State Park, FL
Image: Rod Clement Photography/Getty Images

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Jessica Serna (@mycurlyadventures_) knows how to make the most of a weekend getaway, proving to her followers that even with limited vacation days, you can see the sights and make it home in time for your Monday morning meeting. Here, she shares a jam-packed itinerary for St. Augustine, FL, one of the oldest cities in the United States.

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DAY ONE: Get settled

Exterior of Villa Zorayda Museum
Rooftop pool at Voco St. Augustine
Peruvian tacos at Llama Restaurant
From left to right: Villa Zorayda Museum, Rooftop pool at Voco St. Augustine, Peruvian tacos at Llama Restaurant
Image: From left to right: Kelly B/Tripadvisor, Management/Tripadvisor, jano-staugustine/Tripadvisor

If you arrive in time for lunch, farm-to-table gastropub Prohibition Kitchen does a mean burger with smoked bacon red onion jam, a fried egg, and Red Dragon cheese. Don’t sleep on the Travelers' Choice Award winner's handspun milkshakes either. True to the speakeasy atmosphere, you can add a shot to make them boozy.

Next up is the Villa Zorayda Museum. Built in 1883 in the Moorish revival architectural style, Villa Zorayda has served many purposes: the second home of a wealthy hardware salesman, restaurant, nightclub, and casino. Today, the Travelers' Choice Award winner is on the National Register of Historic Places and operates as a museum that tells the story of the house, as well as St. Augustine. The guided audio tour also details the extensive collection of artifacts, from the exquisite to the unusual, like a 2,400-year-old “sacred cat rug” made from the hair of felines that once roamed the Nile River.

Leave the decorative arts behind and say hello to Art Deco. The exterior of Voco St. Augustine, an upscale IHG hotel and a Travelers' Choice Award winner, is retro in the best way and accompanied by modern amenities like in-room Nespresso machines and a rooftop pool. The hotel’s location also puts you in close proximity to another Travelers' Choice Award winner and one of the best culinary experiences in town: Llama Restaurant. Dine on Peruvian-inspired delicacies and have your phone ready to capture the smoking reveal of the anticuchos, chargrilled beef hearts skewered atop Andean corn and golden potatoes.

DAY TWO: Spend time at the seashore

Crispy crawfish at Preserved
Scenic view of St Augustine beach at sunset
Crispy crawfish at Preserved (L), St. Augustine beach (R)
Image: Management/Tripadvisor (L), Chad Hutchinson/Getty Images (R)

The scenery that comes with the Sensational Sunrise Kayak Tour is enough to make you forget about the 5 a.m. wake up call. Paddle roughly three miles through a lagoon as the first rays of light peek through mangroves and over the sand dunes of nearby Anastasia State Park. The route ends near the St. Augustine Lighthouse, where, after a quick climb to the top, you’ll be rewarded with yet another spectacular view.

Another perk of being up early? You likely won’t have to wait for a table at Ice Plant. Must-try items on the weekend brunch menu include the pineapple upside-down pancake with macadamia nuts and coconut whipped cream and the baked eggs shakshuka with local mushrooms and potato hash. All of the craft cocktails at the Travelers' Choice Award winner come with custom ice cubes, a nod to the building’s previous life as an ice factory.

Quote of Jessica saying, “Any trip to St. Augustine should include a walk around Lincolnville, one of the first freedmen’s towns in North America.”

For more history, head to Lincolnville. The Lincolnville Museum and Cultural Center details 450 years of the African American experience, as well as St. Augustine’s role in the Underground Railroad and Civil Rights Movement. Combine your visit with a walk through the neighborhood and stops along the Freedom Trail, including the home where Dr. Martin Luther King Jr. stayed during his trips to promote desegregation.

When you’re hungry again, grab a slice at Pizza Time and then hit up St. Augustine Beach for a relaxing afternoon in the sun, both Travelers’ Choice Best of the Best winners. Word of advice: Although you can drive on the beach, it’s best to do so in a 4x4 to avoid getting stuck in the sand. For those not looking to offroad, you can park at one of the nearby lots and walk onto the beach.

Return to Lincolnville for a beautifully plated meal inside a historic home at Preserved, a Travelers' Choice Award winner. Here, James Beard Award-nominated chef Brian Whittington pairs elevated Southern comfort foods with a selection of more than 300 wines.

DAY THREE: Take a tour (or three)

Bell tower on the San Carlos Bastion corner of Castillo de San Marcos,
Kayak tour with GeoTrippin Adventure Co.
Shrimp and Grits at Catch 27
From left to right: Bell tower at Castillo de San Marcos, Kayak tour with GeoTrippin Adventure Co., Shrimp and Grits at Catch 27
Image: From left to right: Kenneth_Keifer/Getty Images, Management/Tripadvisor, Management/Tripadvisor

First up is breakfast at Travelers' Choice Award–winning La Cocina International Restaurant inside the Castillo Real hotel, followed by the “Conquistatour of Saint Augustine" Historical Walking Sightseeing Tour. The 90-minute jaunt covers more than 300 years of local history and takes you to culturally significant sites like the Castillo de San Marcos National Monument, a Spanish fort, and the iconic drawbridge known as the Bridge of Lions.

Before your next activity, take a walk or carriage ride down Aviles Street, the city’s original arts district that’s said to be the oldest street in the country. Explore the array of galleries, shops, and sidewalk cafes and keep an eye out for the Red Pineapple Boutique, selling vintage-inspired home decor and colorful dresses.

At this point, you may be hungry for lunch, but hold out. The Travelers’ Choice Best of the Best–winning St. Augustine's Wine, Cocktail and Food Experience tour does not mess around with its full-size “samples.” If you’re lucky you’ll be led by the tour’s founder, Garry, who has plenty of stories and recommendations should you wish to further your culinary education.

Quote of Jessica saying, “Watching the water light up in electric blue was so mesmerizing and no matter how many times I saw it, the wonder and excitement never faded.”

Rally for the final—and arguably most illuminating—tour of the trip: GeoTrippin Adventure Co.’s Bioluminescence Tour. Just before sunset, you’ll paddle out onto Guana Lake and watch the water come to life, glowing in the wake of comb jellies. Nature guides talk you through the science and what’s being done to protect the fragile ecosystem.

Back on land, the Travelers' Choice Award–winning Catch 27 stays open until 10 p.m. on weekends, making it easy to grab one last late-night bite before you pack up and head home.

Jessica’s picks

Biggest surprise: I’m not a big pizza person, but the freshness of the tomatoes in the sauce and the flavors (and size) of the pies at Pizza Time were a pleasant surprise.

Best activity you stumbled upon: The Rum Runners Cruise put on by the Black Raven Pirate Ship! I always see pirate cruises geared toward kids, but when you think about it, pirates are really all about adult humor.

Favorite time of day in St. Augustine: Usually, I would say sunrise because of the way the sun rises over the sea, but we got the most incredible sunset before the bioluminescent tour. It turned the water into a beautiful pinkish purple and made it look like we were floating on clouds.

Decor you’d want to replicate at home: I studied abroad in Spain and can only imagine what it was like living in Villa Zorayda. It’s such a unique space, designed after the Alhambra.

Most photogenic place: The plaza in front of the Lightner Museum—with palm trees and a grand fountain set against the museum’s red stucco architecture—is such a picturesque spot that I want to freeze in time.

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Tommie Ethington
Tommie Ethington is a Dallas-based freelance writer. Formerly an editor for Southwest Airlines' in-flight magazine, she continues to write about travel, design and interesting people for a variety of publications including Condé Nast Traveler, Rolling Stone and Texas Monthly. Find more of her work at tommieethington.com.