Founded in 1565, St. Augustine, located on the Northeastern coast of Florida, is the oldest city in the United States. Whether you come for the history, the architecture, the beaches, or the alligators, you’re sure to appreciate the unique charms of the Ancient City.
WHERE TO PLAY
An afternoon can easily be spent meandering along pedestrian-only St. George Street, where you’ll discover fountains, statues, courtyards, cafes, and art galleries housed in stunning Spanish architecture surrounded by vibrant trees and flowers. The cobblestone lanes of Aviles Street offer a quaint and quiet retreat from busy St. George, with plenty to discover as well. Hop a trolley for a tour of bustling downtown, or take a ghost tour to learn a little otherworldly history by foot. Step back in time with a visit to Castillo de San Marcos, a seventeenth-century Spanish stone fortress that’s now a national monument complete with educational recreations that include marching soldiers and firing canons.
Experience another side to St. Augustine culture with a complimentary guided tour of the St. Augustine Distillery and enjoy sample cocktails featuring small-batch whiskey, rum, gin, and vodka, and their much-loved bourbon in the fall. Stop into the attached The Ice Plant Bar and sip those artisanal spirits in crafty cocktails with house-made syrups, fresh squeezed juices, and hand-carved purified ice. Order some pretzel bread and blue crab beignets to pair with a Florida Mule (made of St. Augustine vodka, ginger, and lime).
Head over the bridge to St. Augustine Beach for white sand, warm ocean water, and shelling along the shoreline. St. Johns County Ocean and Fishing Pier is an expansive pier with souvenirs, snacks, and bait and tackle for sale. Every Wednesday morning locals and visitors flock to the Market at the Beach for fresh produce, baked goods, jewelry, and handmade arts and crafts. Commune with nature at Anastasia State Park wildlife sanctuary, take a tour of the St. Augustine Lighthouse & Maritime Museum, or stop by the St. Augustine Alligator Farm Zoological Park for a gator show.
WHERE TO DINE
Start a day of exploring Old Town with a hearty breakfast or brunch at the charming Maple Street Biscuit Company, where everything is made on-site, including the coffee. Go for one of the signature thick, flaky biscuit sandwiches; the Squawking Goat tops a crispy fried chicken breast with a fried goat cheese medallion and mildly spicy house-made pepper jelly, while the Five and Dime adds pecan wood smoked bacon, cheddar cheese, sausage gravy, and a fried egg to a towering chicken biscuit.
Make a reservation in advance for a romantic, elegant five-star meal at Collage Restaurant in Old Town. Choose a bottle from the excellent, regionally arranged wine list, and start with the luscious house-made burrata with apricot, raspberry, walnuts, and crostini, or the escargot served with tender mushrooms in a puff pastry with brandy cream sauce. The signature Lobster Ravioli is a must, with sautéed shrimp in a pesto cream sauce, topped with a lobster tail, as is the Duo Di Manzo with grilled beef tenderloin medallions and braised short rib stuffed agnolloti over a peppercorn porcini puree with crispy onions.
Make sure to head Uptown and visit the unique, Southern coastal melting-pot cuisine served up by Chef Vinny and Christina at Uptown Scratch Kitchen. Veiled in a portico of fresh herbs and flowering plants, you’ll find a portable kitchen (food truck) serving some of the best bites in St. Augustine. Think shrimp po’ boys, Southern fried chicken, shrimp and grits, arepas, tostones, and Cuban sandwiches. Just grab a seat at a picnic table and order anything on the menu du jour, and prepare to be stunned by food from a truck. Visit early in your trip as you’ll want to come back for another meal!
WHERE TO STAY
St. Augustine is a decidedly B&B kind of city due to its historical nature and Spanish Colonial architecture. An abundance of quaint B&Bs line the streets of Old Town, brimming with Southern hospitality, sumptuous breakfast spreads, and wraparound porches. In the heart of the bustling historic district, on a pedestrian-only street surrounded by attractions, shopping, dining, and pubs, you’ll find the St. George Inn. When not out on the town, take in some people-watching from a rocking chair on the balcony, and enjoy a European-style breakfast by the fountain in the courtyard.
On the quieter side of Old Town, Bayfront Marin House Historic Inn offers views of the Bridge of Lions and boats skimming across Matanzas Bay, with unique, spacious rooms featuring private balconies, canopy beds, and double soaking tubs. Start the day with eggs benedict or fluffy banana pancakes in the gazebo, and kick off your evenings with sangria on the porch swing at sunset during nightly happy hour.
If beach digs are more to your liking, check out the Inn’s sister property Beachcomber Cottages on Vilano; as the name implies, the location on shell-filled Vilano Beach is perfect for the collector of all things shoreline. Whether it’s a one-bedroom suite for two directly on the beach or a Caribbean-style home with a private pool and panoramic views of the Atlantic for the whole crew, this lovely property will fulfill your beach house dreams.