You may think Florida is all beaches and beach towns; but if you’re looking for a weekend away that combines warm ocean breeze with old world charm, look no further than the Sunshine State, where you’ll find the historic St. Augustine.
From its founding in 1565, St. Augustine has evolved over four centuries from a Spanish military stronghold into one of the best reasons to visit North Florida and brush up on your colonial history while soaking up the sun and inhaling the salty ocean air. Canopied pedestrian streets, locally owned boutique shops, historic hotels and inns, and a year-long warm beach breeze make America’s oldest city the perfect place to spend a winter weekend flip-flopping up and down the cobblestone streets.
The Castillo de San Marcos is the obligatory first stop on any St. Augustine tour. Dating back to 1672, the coquina fort, made of tiny crushed seashells from the Atlantic Ocean which it stands guard over, is the oldest masonry fort in the US. Take a tour along the tops of the walls of the centuries-old Spanish fortification, and stay to the end for a live demonstration of the seventeenth century cannon as period reenactors wage a brief imaginary war on the Atlantic Ocean.
From the fort, cross the elaborate Bridge of Lions, named after the marble sculptures guarding the bridge’s entrance, to Anastasia Island. There you can spend the rest of your morning at the St. Augustine Amphitheatre perusing the Old City Farmers Market. Open every Saturday until 12:30, you’ll find everything from fresh caught seafood to organic locally-grown produce, homemade fudge, ceramic handicrafts, and live music.
If you don’t fill up while grazing at the market, grab a light lunch at one of the city’s food trucks, and then treat yourself to the literal and figurative high point of your trip: the St. Augustine Lighthouse. In addition to serving as an active lighthouse guiding ships and fishing boats through the waterways, the building is home to the St. Augustine Maritime Museum, which host exhibits and educational programs about maritime archeology and marine sciences. But the real treats at the lighthouse are the views and the ghosts.
There are several different options for touring the St. Augustine Lighthouse, but whichever one you choose, you’ll have the opportunity to climb the 219 steps of spiraling staircase to the top. From just under the massive lens, you’ll have an unrivaled panoramic view of not just St. Augustine and the ocean, but on a clear day you can see all the way to the Jacksonville skyline some 40 miles away.
Touring the lighthouse at night might not offer the same spectacular views, but for lovers of haunted houses and the paranormal, the Dark of Moon tour will take you through a different side of the lighthouse — the side that’s earned it a reputation as an epicenter of paranormal activity on the Atlantic coast. Popular TV shows like Ghost Hunters have investigated decades’ worth of ghost stories about disembodied voices and shadowy apparitions, but nothing comes close to the creepiness of the real experience.
Sometime during your stay, wash down the lighthouse heebie jeebies with a bottle from the San Sebastian winery. Sourced from vineyards just a few hours away in the Florida Panhandle, you can try San Sebastian’s award winning local wines in any of their daily complementary tours and tastings. Check their calendar of events and be sure to set aside time for a live jazz performance in The Cellar Upstairs, the winery’s very own jazz and blues bar, where you can sip chardonnay to soothing live jazz beats.
Finally, if you’ve got an extra day to escape the town and commune with nature, spend a day in peaceful relaxation at Anastasia State Park, just outside town on Anastasia Island. Rent a kayak or canoe and spend a night camping with the chirping sounds of the estuary ecosystem, or just spend a day strolling the beach and exploring the nature trail where you’ll encounter everything from songbirds to sea turtles.
Head to St. Augustine this winter for the Nights of Lights, when three million bright white Christmas lights radiate out from the town Christmas tree to cover each and every colonial roof and transform St. Augustine into a temperate winter wonderland. For the latest travel deals and local events, as well as tips on lodging and restaurant reviews, check the city tourism website and start planning a historic winter getaway.