A New Old Florida

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America’s oldest city, St. Augustine, sees a new shine

It may be the oldest city in America and steeped in history, but St. Augustine, Florida, continues to reinvent itself with a host of new, modern activities and restaurants. Everything from the city’s architecture and cultural attractions to the food reflects the original Spanish influence—so it’s a place to soak up history in all forms. These days, St. Augustine is also enjoying a new-world revival with an eclectic and vibrant dining scene plus plenty of shopping and culture.

Check in to Check out the Town

Motels are making a comeback for travelers partly due to their nostalgic appeal, and also as a choice for those who prefer to stay in boutique accommodations with personality. St. Augustine’s kitschy motel, the Local, voted Best Roadside Motel in 2022, is everything you want in casual and convenient accommodations in the heart of a historic city.

Dine Where Old Meets New

Several acclaimed chefs are shaking up the restaurant scene by pairing new flavors and cuisines with unique dining experiences. Chef Barry Honan, an apprentice to some of the world’s most celebrated chefs including Eric Ripert and Thomas Keller, recently opened the city’s first modern Japanese restaurant, Lotus Noodle Bar. He’s also created a number of sake craft cocktails that merge local flavors with Asian inspiration.

Asado Life is the culinary brain child of Nick Carrera and Matt Brown featuring a gaucho-style asado (an Argentinean grill handcrafted by Carrera). Guests are treated to dinner with a show as Brown and his team work the asado, grilling meats and seafood over open flames.

Vilano Beach is a sleepy, old-school beach town that is reemerging with a new, more modern personality. Chef Michael Lugo, whose namesake restaurant has been a local favorite in the historic district for years, recently opened Pesca Vilano, the region’s first rooftop restaurant and bar in the newly opened Hyatt Place. Pesca pairs the best of local seafood with Lugo’s trademark bold Latin flavors.

St. Augustine Beach doesn’t get the acclaim of other Florida beaches, but the sand and surf rival any other oceanfront in the state. Today, there’s a new reason to visit in Cousteau’s Waffle & Milkshake Bar, where sweet creations range from hand-spun milkshakes to marshmallow fluff on a s’mores-themed Hennessey waffle to savory waffle combos like prosciutto, fig preserves, and brie.

Play with Your Food

The Tasting Tours are always coming up with new ways to eat-and-experience the city—you can eat and drink your way around town on a walking Corks & Forks Culinary Tour of the historic district as well as a chauffeured Sunday Boozy Brunch Tour. And if you want a hands-on course in St. Augustine’s food scene, take a class at the Ancient City Cooking Experience, which dishes out classes on everything from creating artful charcuterie platters to preparing romantic date-night dinners.

Explore the Walkways and Waterways

While St. Augustine is one of the South’s most walkable towns, e-bikes and scooters have increased in popularity. You’ll want to stroll outside the historic district along the city’s main thoroughfare, San Marco Street, and peruse the eclectic and unusual boutiques. If you’re headed over to Vilano Beach to check out the emerging scene, the water taxi is the best way to avoid traffic. Speaking of which, this city is best appreciated from the water, so book a sunset cruise with St. Augustine Sailing.

Be sure to catch a concert at the St. Augustine Amphitheatre (“the Amp” to locals), one of the top-selling amphitheaters in the world, and also one of the coolest outdoor venues—it’s yet another way to discover the pairing of Old World with the New.