Miles from Naples: 300
The story of present-day Florida originates in St. Augustine. The Spanish arrived in 1565, forming what would become the oldest, continually occupied European settlement in the United States. Henry Flagler established a small collection of grand hotels here in the late 1800s, introducing this coastal town to his wealthy contemporaries and creating an infrastructure for work and play. Modern St. Augustine has one foot planted in the past, with a downtown historic district marked by centuries-old monuments, Colonial buildings, and ghostly inhabitants. But the Old City of tomorrow is fast becoming a hip haven for foodies, entertainment junkies, and history buffs.
Stay: A visit to the Casa Monica Resort & Spa (casamonica.com) starts in the original carriage entrance and continues into the opulent Moorish lobby with hand-painted frescos and chandeliers reminiscent of a Moroccan riad. This fairy tale of visual jewels is very real. A member of the National Trust Historic Hotels of America, Casa Monica was built in 1888 by Franklin W. Smith. Roughly a century later, in 1999, it received a complete renovation and became a Kessler Collection hotel. Restored to its former glory, the Casa Monica is the place to stay in St. Augustine, both for its glam appeal and central location. This boutique hotel boasts 138 rooms outfitted with Spanish-style furniture, as well as suites configured into multi-floor layouts. Prepare for a day of sightseeing at the nearby Poseidon Spa or relax in a personal cabana at the pool. Later, venture to the Cobalt Lounge for a cocktail and live music before savoring Mediterranean tapas at Costa Brava.
See + Do: Downtown St. Augustine is supremely walkable. However, some attractions are a mile or more away, and the best way to see them all is via Old Town Trolley Tours (trolleytours.com). A pass allows you to hop on or off any of these orange-and-green streetcars at more than 20 spots; some of the most popular include the Old Jail, designed to resemble a Victorian home; Castillo de San Marcos (nps.gov/casa), constructed in the 1600s and known colloquially as “The Fort;” Ripley’s Believe it or Not! (ripleys.com/staugustine), an infamous house of oddities; and Ponce de Leon’s Fountain of Youth Archaeological Park (fountainofyouthflorida.com), where timeless beauty exists in the form of native flora and a muster of peacocks.
When traveling by foot, begin next door to the Casa Monica at the Lightner Museum (lightnermuseum.org). Formerly Flagler’s Alcazar Hotel, the Lightner provides a snapshot of the Gilded Age. Hear the sounds of the early 1900s with a demonstration of antique musical instruments. Stroll down a turn-of-the-century shopping plaza outfitted with glass novelty hats, bohemian jewelry, and vintage kitchen utensils. Be sure to venture upstairs for a glimpse inside the Alcazar’s former Russian bathhouse.
Other St. Augustine mainstays are St. George Street, a pedestrians-only commercial thoroughfare, and the St. Augustine Amphitheatre (staugamphitheatre.com), which hosts performers year-round. For a panoramic view of it all, climb the 219 steps to the top of the St. Augustine Lighthouse (staugustinelighthouse.com).
Eat: Look beyond the tourist trap seafood joints in favor of St. Augustine’s homegrown culinary scene. The Floridian (thefloridianstaug.com) specializes in comfort food with a locavore twist, as seen in dishes like Pork & Waffles with pulled pork atop a gluten-free waffle bathed in a bourbon-brown sugar glaze, seasonal fruit, Florida honey, and homemade ricotta.
For a less folksy, more of-the-moment meal, head over to Ice Plant Bar (iceplantbar.com), which elevates the cocktail experience to an art form, featuring libations made using house-pressed juices, local ingredients, and three kinds of ice. The food is just as impressive. The pickled shrimp toast improves on a local favorite with the addition of a madras curry aioli and jalapeño.
Bookend any—or every—day with heavenly baked goods. Maple St. Biscuit Co. (maplestreetbiscuits.com) slings up creative biscuit sandwiches, with orders called out based on your favorite TV show instead of your name. Breakfast becomes a decadent dessert at Cousteau’s Waffle & Milkshake Bar (wafflemilk.com), which uses Belgian pearl sugar and house-made ice cream.
Hot Tip: St. Augustine is one of the country’s most haunted destinations. There are dozens of ghost walks to choose from, but the Ghost Augustine Haunted Pub Tour (ghostaugustine.com) adds liquid spirits to the equation. This adults-only outing—part bar crawl, part ghoul hunt—is a great way to make fast friends, both living and dead.