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.


In our Where To series, we tag along as eight fascinating travel influencers jaunt from coast to coast in search of the best meals, experiences, and more, all inspired by our Travelers’ Choice Awards. Browse all of the itineraries on our Where To hub.
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.
Save all the things you love
Tap the heart on any place mentioned below to save all your travel ideas in one place and build a custom itinerary. Learn more.
DAY ONE: Get settled



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


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.

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)



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.

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.

