The entrance to Casa Monica Resort & Spa in St. Augustine is a quick right turn off King Street into a narrow cobblestone passageway where uniformed valets look as if they might be ready to stable your horse after it clippity-clops to a stop. But this is 2019, 131 years after this Moorish Revival-styled hotel opened, so the boys at the valet station whisked our car away and we walked into a grand lobby of hand-painted gold leaf ceiling beams, an Italian-tiled fountain and heavy Spanish furniture. At check-in, we were promptly greeted with a complimentary glass of champagne. My twin sister and I glanced at each other. This was going to be a wonderful birthday weekend.

Our room was a huge corner suite overlooking busy King Street, lovely Flagler College and the manicured plaza outside the Lightner Museum. The suite, fittingly, had dark leather chairs and a couch, heavy floor-length drapes and was decorated in golds, reds and browns. If you want a luxury beach getaway with crisp whites and a minimalist feel, this is the wrong hotel. 

We loved the Old World charm and plopped down on the couch to plot our adventures in history. We were in St. Augustine, after all, the nation’s oldest continuously populated city, and staying in one of Florida’s—and America’s—oldest hotels.

At five stories, 138 rooms and 14 suites, Casa Monica is beautiful. Designed by architect Franklin W. Smith, who purchased the land from railroad pioneer Henry Flagler in 1887, it features the signature ornate balconies, towers, parapets, arches and red tile roofs of the Moorish style. It opened on New Year’s Day 1888, but only four months later, Smith encountered financial problems and sold it back to Flagler for $325,000. Flagler renamed it the Cordova, made some ambitious changes, and then abandoned the property during the Great Depression. There it stood until the 1960s when it became the St. Johns County Courthouse. In the mid-’90s, hotel developer Richard Kessler purchased the courthouse for $1.2 million and returned it to its original splendor and name.

Like all Kessler Collection properties, wine, music and fine art are fixtures, and Casa Monica’s lobby is adorned with paintings. The hotel also has the serene Poseidon Spa and a pretty outdoor pool area. We considered trying a massage or facial, but the city was beckoning. No time to relax on this trip.

A knock on the door brought a charcuterie tray piled with delicious olives, pickles, cheeses and a bottle of red wine. Fueled for our day on the town, we headed outside, making note of the hotel’s comfy Cobalt Lounge where a jazz band was attracting a crowd, and, just beyond, the hotel’s well-regarded Costa Brava restaurant.

St. Augustine is a walkable city, and Casa Monica is in the perfect location to explore the entire downtown. We tried one of the ubiquitous trolley tours but soon hopped off to sightsee on our own. The historic downtown and its residential streets are worth strolling. Mega mansions are nonexistent. Homes retain their original charm and big front porches, and most have lovingly tended gardens, so we walked for hours.

The next morning, we grabbed cappuccinos from the lifesaving Starbucks off the lobby and headed to Castillo de San Marcos, the 1672 Spanish-built fort on Mantanzas Bay. Unfortunately, we were there during the federal government shutdown, so we could only explore the exterior. We avoided the wax museums, Ripley’s Believe-It-or-Not! and pirate treasure attractions. Instead, we discovered the tiny Father Miguel O’Reilly House Museum on Aviles Street, which was built in the late 17th century and housed French nuns, who later played a role in educating liberated slaves after the Civil War.

Hotel employees planned our day of eating and drinking: lunch at the funky Floridian, for “innovative Southern fare for omnivores, herbivores and locavores.” (Try the fried green tomato salad and the rosemary cucumber lemonade.) For our birthday dinner, we ended the evening at The Preserve. It’s a charming old home with a wraparound porch and twinkling white lights that serves Southern cuisine with local, seasonal ingredients prepared by a chef once called “one of the best chefs in the South” by the James Beard Foundation.

The next morning, we woke up early to enjoy the famous brunch at Casa Monica’s Costa Brava. The buffet tables groaned—and so did we—under the weight of unlimited Alaskan snow crab, fresh-made omelets, Mediterranean fare, crepes, pastries and fresh fruit. We managed to heave ourselves into the car for the four-hour drive back to Sarasota. We also managed to make one more stop. My thrift store-obsessed sister spied Ayla’s Acres Thriftique just as we were leaving town. “I’m pulling over,” she declared. I found an adorable white dress with black pinstripes for $8 and a pair of funky hot pink Bakelite earrings for $3. It was indeed a wonderful birthday weekend.   

Casa Monica | 95 Cordova St., St. Augustine, (904) 827-1888, casamonica.com |Room rates begin at $199 weekday; $319 weekend. | Distance from downtown Sarasota: 4 hours.

Things to Do

Visit the Lightner Museum

Built by Henry Flagler, the Lightner Museum was once the Alcazar Hotel and connected to the Casa Monica. Magazine publisher Otto Lightner purchased the property in 1946 and turned it into a museum, and today it’s filled with costumes, furnishings and items of America’s Gilded Age. lightnermuseum.org.

Play tourist on St. George Street

Yes, this pedestrian mall is touristy, but it has fun shopping—whether it’s hippie clothes, cool ceramics or handmade jewelry and gifts—the Colonial Quarter, and some terrific places to grab a bite.

Chill out at the Ice Plant

Built in 1927 and remodeled in 2014, the Ice Plant is a bar and restaurant with a great factory-décor vibe, packed shoulder-to-shoulder with beautiful people drinking craft cocktails. iceplantbar.com.