St. Augustine Photo: Fotolia
St. Augustine Photo: Fotolia

St. Augustine, Florida

America's oldest city offers much more than its many historic landmarks.

September marked the 450th anniversary of the founding of St. Augustine, Florida, the oldest continually occupied European settlement in America. The thriving, quirky city of 14,000 is a tourist magnet, and not just because of its historic landmarks and vintage buildings.

Fine restaurants permeate its walkable downtown, where historical interpreters and costumed pirates roam the alleys along with clip-clopping horses pulling carriages. Art walks, festivals and parades accompany many holidays and other special occasions. The European charm of narrow cobblestone streets, balconies adorned with cascading flower boxes and intricate Spanish architecture also help explain why Forbes named St. Augustine in 2012 as one of America’s 10 prettiest towns. That same year, National Geographic selected it as one of the “World’s Top 20 Places to See,” one of only four in the U.S.

Many visitors begin a tour at the Castillo de San Marcos, a U.S. National Park Monument. Construction using coquina (shell-stone) rock began in 1672, and the structure stands as the oldest masonry fort in North America. Pounded by cannon fire for 27 days in 1740 by Georgia’s British general, James Oglethorpe and his troops, the fort never fell. Now the daily canon firings are by costumed National Park Rangers and volunteers.

You’ll find 36 buildings of Spanish and British colonial origin still standing in the historic district, including the 1600s Gonzalez-Alvarez House, the oldest Spanish dwelling. The Spanish Military Hospital Museum should appeal to anyone interested in medicine. This building, on often-photographed Aviles Street, is an authentic reconstruction of a military hospital that stood there from 1784 to 1821. Also worth seeing is the Fountain of Youth Archeological Park, one of Florida’s earliest tourist attractions and a tribute to the place where Ponce de Leon is said to have landed in 1513.

After Florida became a state in 1845, Spanish influence faded and Gilded Agers discovered St. Augustine. In 1888, Standard Oil magnate Henry Flagler constructed the East Coast Railroad and the elegant Ponce de Leon Hotel for his friends, the luxury travelers of the era. Now, this turret-and-tower Spanish Renaissance jewel is a centerpiece for Flagler College. Tours of the former hotel begin in the fountain-centric courtyard and proceed into the grand lobby with its magnificent 80-foot domed ceiling supported by eight hand-carved oak caryatids. Another attraction is the dining room, with its 79 Tiffany stained-glass windows. Thomas Edison personally installed the hotel’s electrical lights and prized clock.

Flagler, who became known as the father of Florida tourism, built a second hotel directly across the street that now serves as City Hall.

Want a stunning, bird’s-eye view of St. Augustine? You can don an old-fashioned leather flying helmet like a barnstormer of the 1920s and 30s and take a sightseeing ride in an open-air biplane. The Waco was built in 2011 but was designed to look and fly like a 1935 model. Helicopters provide another aerial touring option, day or night. You can soar over the waterways in a Robinson R44 helicopter to North Beach and Porpoise Point and then fly above the city.

Speaking of the waterways, the Matanzas Inlet proved treacherous for early navigators, with its significant tidal changes and shifting sandbars. Many a vessel went down in the offshore waters. To aid navigation, Spanish settlers built wooden watchtowers, followed in 1824 by the first St. Augustine lighthouse. The current lighthouse and keeper’s house date back to 1874. Climb the lighthouse’s 219 steps for panoramic outlooks of surrounding waterways, and visit the adjacent maritime museum. An archeology tour provides a fascinating glimpse at ongoing research for those interested in shipwrecks.

While flying into St. Augustine is easy, you can also arrive on your boat like the Spaniards did from the Atlantic or from the modern Intracoastal Waterway. Experienced skippers can rent sailboats or hire a captain for a seafaring adventure. Others choose a relaxing sail on the Schooner Freedom or a paddle on ecological kayak tours of the estuary. You can also walk the gangplank on El Galeón, a replica of a ship that traveled the coasts of Florida between the 16th and 18th centuries.

Fishing is huge in Florida. Choose from saltwater and freshwater, inland and deep-sea. Redfish, black drum, sea trout, flounder, sheepshead and tarpon live here. Charter fishing boats offer reel therapy on half- or full-day outings.

St. Augustine’s seashore stretches from Vilano Beach north of the city to Crescent Beach in the south. Try St. Augustine Beach, on Anastasia Island just over the famous Bridge of Lions. Driving is permitted within designated areas on the white-sand beach.

Beautiful beachside scenery offers a backdrop for the area’s more than 1,200 holes of challenging golf. The ultimate destination for golfers is the Players Club and Clubhouse at nearby Ponte Vedra Beach. It’s home to the Players Championship, golf’s “fifth major.” The clubhouse (open to the public) is also a draw, with volunteer storytellers in the lobby and escorted golf-cart rides to the final three holes, including the famous 17th island hole, considered the most photographed hole in golf.

At the World Golf Hall of Fame within the World Golf Village in St. Augustine’s suburbs, check out the locker-room area where mementos chosen by the inductees represent their individual stories. The spectacular trophy room displays many championship cups. You’ll also find a family-friendly, 18-hole outdoor natural-grass putting green.

Pirate raids, part of the history of this region, are the inspiration for more family fun. A deadly sack of the town in 1668 by pirate Robert Searle is colorfully re-enacted annually. The Pirate and Treasure Museum features one of only three Jolly Roger flags in existence, the only known authentic pirate treasure chest and Jack Sparrow’s sword from the Pirates of the Caribbean movies. Cruise aboard the Black Raven, St. Augustine’s resident pirate ship, for swashbuckling fun.

The Alligator Farm, a zoo founded in 1893, attracts bird watchers and photographers from February to May. The huge gators keep predators away so thousands of egrets, herons, roseate spoonbills and wood storks return to the rookery each year.

The Colonial Quarter, which feels like a mini-Williamsburg, brings the city’s Spanish and British heritage to life with a leatherworking shop, a blacksmith, a print shop and an 18th-century home. The ruins of Fort Mose—the first legally recognized free community of ex-slaves, established in 1738—offer an important piece of black history.

To maintain its ambiance, St. Augustine requires that all restaurants within the historic district be privately or chef owned; no chains are allowed. A culinary tasting tour is one of the best ways to sample the fare, which ranges from Spanish tapas to French patisseries to Mexican favorites and pizza by the slice on touristy St. George Street.

Free tours and tastings take you through the St. Augustine Distillery, which produces gin, vodka and whiskey from local ingredients and Florida-grown sugarcane. Bartenders incorporate the distilled spirits into outstanding artisanal cocktails. At the tastings that follow, try the Florida Mule, a house specialty at the Ice Plant, the upstairs restaurant. It’s a great way to end a day in this majestic and unforgettable city.

Traveler Fast Facts


America’s oldest city, with colonial Spanish charm and Gilded Age buildings, located midway between Daytona Beach and Jacksonville, Florida. Outstanding golf, cuisine and seaside activities help make it a desirable vacation destination.


Northeast Regional Airport, formerly St. Augustine Airport, lies four miles north of the historic district with three asphalt runways (the longest is 8,002 feet) and two seaplane lanes. Daytona Beach Airport, 50 miles south, sits next to Daytona International Speedway and offers three runways and a six-gate domestic terminal. Major airlines serve Jacksonville International Airport, 50 miles north. Private watercraft may book reservations at the Municipal Marina.


St. Augustine basks in a warm, humid climate with hot summers and no dry season or snow. On average, there are 223 sunny days per year. The July high is around 90 degrees, and the January low is 46.

Traveler Report Card


Casa Monica Hotel (A+), built in 1888, caters to luxury travelers. Located in the historic district, it features a Spanish-themed lobby that feels like the Alhambra and includes the seductive Moroccan-style Poseidon Spa. St. Francis (A) is the oldest of the city’s popular bed-and-breakfast inns, yet it features updated amenities, including a battery-charging station for Teslas. Casa de Suenos (A) offers a stylish modern feel while the Pearl of the Sea (A) presents 10 rooms, including eight with patio views, on Anastasia Island. The nearby Ponte Vedra Inn & Club (A+), a five-diamond oceanside facility, offers two guest-only, 18-hole golf courses, a 30,000-square-foot spa, a beach and pools. With access to six courses, the Sawgrass Marriott (A) at the The Players Championship course makes ideal lodging for golfers.


In the historic district, try Costa Brava (A) in the Casa Monica Hotel. For intimate dining on international cuisine, Collage (A) is a great bet. Columbia (A) features authentic Spanish tapas and decor. Lunch and cocktail notables are the Ice Plant (A) and the Tini Martini Bar (A). Breakfast favorites include La Herencia (B) for Cuban food and the French Patisserie (B) for croissants and macaroons. Don’t miss the memorabilia, food and drink at the Murray Brothers’ Caddyshack Restaurant (B) at World Golf Village.


St. Augustine should please romantic couples, luxury travelers, family groups and individuals interested in cultural and historical attractions, boating, fishing, beaching, golfing or just relaxing. Photographers and birders love the area, too. Major regional events include Amelia Island Concours d’Elegance in March, the Players Championship in May and the Daytona 500 in July. St. Augustine Nights of Lights, which runs from Thanksgiving through January, dazzles with over three million white lights outlining the buildings, bridges and trees of the historic district.

A Little History

When Juan Ponce de Leon landed in what he called “La Florida” in 1513, he claimed the region and all its gold and treasures for the king and queen of Spain. Myth says he was searching for the Fountain of Youth. He didn’t find that—or any gold—but he did discover lush green landscapes sparsely populated by friendly Native Americans, and bountiful fruit and fish.

In 1565, the crown sent Spaniard Pedro Menendez de Aviles to establish a colony, as well as run off the French, who had settled near Jacksonville. Menendez named the settlement “San Agustín,” having first sighted the coast on the feast day of Saint Augustine. The city served as the capital of Spanish Florida for more than 200 years and was designated the capital of the Florida Territory until Tallahassee took over in 1824. Disputes with pirates, skirmishes in the Revolutionary War and territorial wars with the Seminole tribe contributed toSt. Augustine’s storied past.

Debi Lander, a frequent BJT contributor, lives within the historic district of St. Augustine.