What it is

A fanciful 1888 hotel reborn for today’s traveler with 124 luxe rooms, a serene spa and cabana-lined pool, two Mediterranean restaurants and even an on-site Starbucks.

What it isn't

Just lolling by the pool. The expertly stocked fitness center has all you need to feel ready for Florida’s persistent swimsuit weather.

What we think

They don’t build hotels like this anymore: a Moorish Revival castle that looks like a fairytale sprung to life and was once owned by railroad magnate Henry Flagler. Today, guest rooms are as charming as ever, with ornately tufted red velvet headboards and curved archways, but they’re cozy—starting at 150 square feet (hey, it’s as historic as they come). For a sprawling experience more suited to Mr. Flagler himself, we recommend the one-bedroom bi-level 612-square-foot Ponce de Leon suite, which has a canopied four post iron bed, a whirlpool jacuzzi tub big enough for two, private balcony, quirky furniture and accessories (yep, that’s a tasseled floor lamp) and comped sangria. Of course, you’ll want to make like a tycoon and take your tipples at the Cobalt Lounge, where they have a full menu of cocktails mixed with locally made liquors. (Order the Florida Mule, with St. Augustine Sugar Cane Vodka).

You're here because

The spa here is also a salon, and you love to add full, Real Housewives-level “glam” makeup treatments and blowouts to your body scrubs and massages.

The Moment

Ensconced in your silvery corner booth at Costa Brava, you’re feeling as boho as the chandelier gleaming overhead. Your order? A harissa grilled chicken with charred broccolini, cauliflower and corn sofrito. And, this being Florida, a Rum Tiki cocktail with toasted coconut. #Vacay vibes, indeed.

Restaurants & Bars

Costa Brava - Mediterranean cuisine

Cobalt Lounge - Continental

Location

Historic downtown St. Augustine, just four blocks from the banks of the Matanzas River. While you’re here, be sure to duck your head in the neighboring Lightner Museum, a Gilded Age hotel that’s now a showcase for 20,000 works of art and antiques (look for Louis Bonaparte’s 1806 escritoire desk, inlaid with ivory.