Known as the Ancient City, St. Augustine features centuries-old architecture, iconic cultural sites, and unspoiled beaches.

By Kara Franker
May 02, 2019
Historic St. Augustine from the Matanzas River.
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The Fountain of Youth is calling your name—just like it called to the Spanish explorers more than 500 years ago. Maybe it’s those gorgeous beaches or maybe it really is something in the water. Either way, there is lots to explore in this charming city on Florida's Atlantic coast.

St. Augustine is Florida’s Historic Coast

Most people don’t realize that St. Augustine is the oldest continuously inhabited European settlement in the United States. (It was preceded by Puerto Rican colonies; Pensacola, which was destroyed in 1559; and Fort Caroline in Jacksonville, Florida, destroyed in 1565.) In fact, Ponce de Leon claimed “La Florida” for Spain in 1513, which is decades before the Jamestown colony in Virginia, and long before the Pilgrims arrived at Plymouth Rock in Massachusetts. Over the centuries, many cultures have called the city home, including Native American, Spanish, British, French, and African.

Interestingly, we tend to learn more about English history in school instead of Spanish history—so that’s why not as many Americans have a full appreciation for Florida’s Historic Coast, which includes both St. Augustine and Ponte Vedra Beach. Besides the gorgeous beaches and historic sites, there are great restaurants, plenty of opportunities to listen to live music, and lots of friendly folks in this charming seaside destination.

A sentry box turret overlooks Matanzas Bay at the Castillo de San Marcos
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Historical Icons in St. Augustine

One of the most architecturally significant structures in the city, and also the oldest masonry fort in the country, the waterfront Castillo de San Marcos is truly a sight to behold. Originally built in the 17th century, the national monument is made of native coquina stones—which absorbed or deflected enemy projectiles, giving the Spanish a special advantage. Climb to the top of the fort and check out the incredible views of the city and waterfront.

Just two miles north of Castillo de San Marcos, Fort Mose Historic State Park is the location of the first free African settlement in North America. Learn about this important 40-acre historical site and stick around to spot some of the natural wonder and current residents like bald eagles and blue herons.

Take a sip from the legendary fountain at Ponce de Leon’s Fountain of Youth Archaeological Park, which tells the story of the birth of St. Augustine, as well as the Timucuan people who preceded the Spanish by thousands of years. Walk through the lushly landscaped park (dogs are also allowed) to sample water from the bubbling fountains.

St. George Street
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Experience history come alive in the Colonial Quarter, located in St. Augustine’s historic district along St. George Street. The two-acre attraction takes you on a journey through the 16th, 17th, and 18th centuries. Learn about blacksmithing, watch a live musket demo, and climb to the top of the 35-foot watchtower for panoramic views of St. Augustine’s bayfront and the historic Castillo de San Marcos.

Fast forward to the early 20th century, when oil tycoon Henry Flagler got his own taste of the bounty this shoreline has to offer. He developed St. Augustine into one of the country’s first winter resort destinations. Paying homage to the city’s great past, the millionaire developer built the stunning Ponce de Leon Hotel (now Flagler College), with its opulent 80-foot domed ceiling and Spanish Renaissance architecture.

Saint Augustine Lighthouse at Anastasia Island
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More Fun Things To Do in St. Augustine

There are so many great opportunities to explore St. Augustine, whether it be via a horse-drawn carriage ride, historic walking tour, or a hop-on-and-off trolley ride. A variety of tour operators can craft an experience to fit any taste, whether it be culinary, historic, or even paranormal (yes, we’re talking ghosts). Legend has it that St. Augustine is one of the most haunted cities in America. Whether you’re a believer or a skeptic, be prepared to be entertained (and maybe a little frightened) on Ripley’s Ghost Train Adventure, Old Town Trolley’s Ghost & Graveyards Tour, or Ghost Tours of St. Augustine.

St. Augustine Lighthouse is rumored to be haunted too, but during the day it’s a perfectly ghost-free (they only come out at night, right?) and gorgeous site to see. Located halfway between downtown St. Augustine and the beaches of Anastasia Island, it’s the oldest navigational site in North America and home to a maritime museum. Climb up the 219 steps to the top of the lighthouse and check out incredible views of the water and city.

Speaking of the water, there are plenty of opportunities to enjoy the sea and year-round balmy weather. Help hoist the sails of the Schooner Freedom, a massive topsail schooner captained by John and Sarah Zaruba. Or cruise aboard a mahogany paneled Matthews yacht courtesy of Ancient City Charters, perfect for a romantic sunset sail. If you’d like to try your luck with a rod and reel, get offshore or on the flats on a fishing excursion with professional guides like Sea Love Charters or Drum Man Fishing Charters.

There are plenty of places to listen to live music in the oldest city. Just walk along the streets of downtown where a variety of restaurants host live bands. The St. Augustine Seafood Company hosts free concerts at their on-site Colonial Oak Music Park. Known as The Amp, the 4,000-seat St. Augustine Amphitheatre hosts a number of ticketed live music performances throughout the year. Located a little farther north, the Ponte Vedra Concert Hall is another popular performing arts venue.

Crescent Beach, south of St. Augustine
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The Best Beaches in St. Augustine

While Florida’s Historic Coast is most famous for its storied past, make sure you leave plenty of time to kick back on the area’s unspoiled beaches. Home to the popular St. Johns County Ocean and Fishing Pier, St. Augustine Beach offers a large oceanfront pavilion, splash and play park, sand volleyball courts, and plenty of seaside restaurants like Salt Life Food Shack and South Beach Grill.

Just north of St. Augustine Beach, Anastasia State Park is a pristine stretch of sand with abundant wildlife and natural tidal marshes. There’s a coquina quarry where laborers mined stones to build the majestic Castillo de San Marcos and other historic structures in downtown.

In the northern part of St. Johns County, Ponte Vedra Beach is famous for its historic and luxurious resort town feel. It’s also the site where, according to navigational records, Ponce de Leon first set foot on Florida sand. View the exact spot at the Guana Tolomato Matanzas National Estuarine Research Reserve, 73,000 acres of protected coastal dunes, tidal lagoons, and forests. It’s a gorgeous location to hike, bike, fish, kayak, picnic, and ride horseback. There are over nine miles of nature trails, as well as a prehistoric earthen burial mound, and 17 additional archaeological sites.

Caps on the Water in Vilano Beach, across the Tolomato River from St. Augustine
courtesy of Florida’s Historic Coast

The Best Restaurants in St. Augustine

There are plenty of options to taste the local flavors along Florida’s Historic Coast. There are several culinary tours that give you the opportunity to sample cuisine from the many destinations that have influenced the city’s history including Spain, France, Italy, Asia, Mexico, and the Caribbean. Check out The Tasting Tours and City Walks Savory Faire Food Tours. And you’ll definitely want to tour the St. Augustine Distillery, where you can sample small batch spirits in a restored ice plant dating back to 1907.

Two crowd favorites equally famous for their water views and oyster bars, dine at Meehan's Irish Pub & Seafood House in the heart of the historic district, and Cap’s On The Water in Vilano Beach, which has killer sunset views because it faces the Intracoastal Waterway to the west. Nearby to Cap’s, also check out Aunt Kate’s, a family-owned waterfront eatery that has a tradition of serving Menorcan dishes, fresh seafood, and a famous clam chowder for more than 100 years. The family’s history dates back to several indentured servants from the island of Menorca, who fled the failed English Colony at New Smyrna to safety in St. Augustine in 1768. And while the original restaurant succumbed to fire, the new building is serving up the same great recipes on the water.

And, of course, that delectable Southern style cooking is what many foodies have grown to know and love about St. Augustine. Supporting local growers and producers, The Floridian features a fresh regional take on traditional down-home fare like fried green tomatoes, peppered shrimp, barbecue pulled pork and waffles, and the “Dixie” burger. Another local favorite, Catch 27 is a made-from-scratch kitchen that serves up hefty helpings of fried buttermilk chicken, grits, and deviled eggs.

For an artisan-style after dinner treat, head to Hyppo Gourmet Ice-Pops or Peace Pie in the historic district, or nearby Whetstone Chocolates of St. Augustine, which offers a chocolate tasting tour.

The Best Hotels and Resorts in St. Augustine

Blending romance and history together seamlessly, The Collector Luxury Inn & Gardens is a high-end bed and breakfast with the ambiance of a luxury boutique hotel. Located on a one-acre property in the heart of downtown St. Augustine, the inn features elegant guest rooms and suites that have been completely restored inside a collection of nine vintage structures—the oldest dating back to 1790. History abounds as you wander through lushly landscaped gardens and bubbling fountains. And you’ll be in good company. A Colonial Revival residence that was built in 1909 once welcomed visitors like Mark Twain and Sinclair Lewis.

A waterfront gem located within walking distance to all the historic sites in downtown, the Hilton St. Augustine Historic Bayfront hotel offers great views of the Bridge of Lions and Mantanzas River. 

Related: 10 Best Little Beach Towns in Florida

Or if you’re looking for a lavish beachside escape, the Ponte Vedra Inn & Club is a AAA Five-Diamond stunner with a storied past. It originally opened in 1928 and has been attracting the who’s who of well-heeled guests for nearly a century. A major perk is the resort’s 36 holes of serene seaside golf. And there’s tennis, kid’s activities, a beautiful spa, and lots to do on the beach.

The destination’s newest hotel is Embassy Suites by Hilton St. Augustine Beach Oceanfront Resort. Nestled between the St. Augustine Beach Pier Park and the 1,600-acre Anastasia State Park, the resort provides lots of opportunities for water sports, nature hikes, and access to miles of pristine undeveloped beaches.

Flagler College
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When to Go to St. Augustine

It’s a toast of historic proportions. Dating back to when Pedro Menéndez and the first European settlers arrived on the shores of St. Augustine more than 450 years ago carrying loads of wine from Spain, the historic city has become known as America’s Spanish wine capital. Celebrating this unique heritage, the St. Augustine Spanish Wine Festival takes place in February and features a series of special events that feature Spanish wine, cuisine, and culture. And all proceeds from the festival benefit local charities.

Let the rhythm move you at the annual Sing Out Loud Festival in September. Including everyone from big name headliners to local talent and songwriters, the event takes place for almost the entire month of September and features live music performances at venues around the city. The best part? It’s the largest free music festival in Florida.

The entire city of St. Augustine transforms during the holidays for the annual Nights of Lights celebration. Wander through the historic district and witness magical displays of millions of Christmas lights. And there are lots of special holiday-themed events like the Holly Jolly Shopping Spree, the beer infused Nights of Pints, Villa Zorayda’s annual Candlelight Tour, holiday concerts, craft festivals, boat parades, and more. The festival kicks off the Saturday before Thanksgiving and continues nightly through January.

Whether you stroll through the brick streets of Old Town or kick back on the beach, Florida’s Historic Coast is a great place for a family vacation.

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