Cities That Surprise: St. Augustine, Florida

As the oldest continually occupied city in the United States (settled in 1565!), St. Augustine, Florida is full of stories to tell. It has all the benefits of a close-knit small town with the added benefits of surreal scenery, rich history and creative inspiration. St. Augustine boasts residents whose families have lived in the area since the city’s very beginning, but its cultural offerings also attract artists, transplant and surfers from all over the world looking for a slower pace of life; which makes for a stimulating mix of world views and conversations everywhere you turn in town. Nestled on the northeastern coast of the state, the city isn’t quite your typical beach town. For starters, while you’ll find Florida sun and 90-degree heat in the summer, you may find yourself in need of a sweater or cute fall jacket come January. St. Augustine certainly attracts spring breakers, but has too many family-friendly tourist get-ups to give off an all-out MTV beach party vibe – it’s the perfect mix of a little bit of everything.

St. Augustine Beach

If you pay a visit, your home away from home at one of the charming B&Bs in one of the historic district’s gorgeous houses, or if you’re in the mood for a splurge, check into the beautiful Casa Monica Hotel. Start your day on Anastasia Island, just across the bay over the historic Bridge of Lions. Get yourself brunch at Cafe Eleven, a cozy coffee shop by day/music venue by night directly across the street from the Atlantic Ocean. Head to the beach and bask in the sun for as long as you please, and if you’re there on a Saturday, visit the farmers market at the St. Augustine Amphitheater and make friends with the some of the city’s talented residents. One of the more popular attractions on the island is the local lighthouse, which rewards you for your tumultuous trek up its winding staircase with a beautiful view of town. Bonus points if you visit the nearby Alligator Farm!

St. Augustine Lighthouse

St. Augustine Lighthouse

The first thing you’ll notice on the island is the wall of greenery that greets you alongside the main road and coats the side streets.

St. Augustine

It’s like peeking into rows of tiny tucked-away jungles. Walking underneath the Spanish moss in the dappled sunlight is a tiny slice of heaven on earth, and may compel you to spend the next five moments seriously considering selling all your shit, buying a beach house and never leaving again, despite the growing panic in your travel buddy’s eyes as you describe this idea.

St. Augustine

A great place to see more greenery on the mainland is Magnolia Avenue. The Fountain of Youth Archaeological Park is on Magnolia (and the fountain itself leaves much to be desired, trust), but the real star of the show is the surreal Spanish moss canopy that envelops you as you make your way down the block. Other places to find some sacred, nature-filled peace are the grounds near Mission Nombre de Dios Rustic Altar and Tolomato Cemetery (which is periodically open to the public and has not been in use since the 1800s).

Back on the mainland, give yourself a few hours to meander around the city on foot without much of a plan. St. George Street near the center of town is the area’s main tourist drag, so keep your eye out for the gems vs. your run-of-the-mill overpriced t-shirt shops. Pay a visit to the tiny tucked-away Yo Ho Ho Beads and peek into St. Augustine Art Glass and duck into their charming backyard space for a slice of heaven. Stop inside the Spice & Tea Exchange and pick up a signature blend to make a taste of Florida at home. Stop by clothing and thrift shops like The Closet and The Way We Were, and peruse the local art galleries.

St. Augustine

Be sure to make your way down Charlotte Street, Avilles Street, and Hypolita Street; and comb your way around the city’s quieter side streets to imagine what life must be like in one of the beautiful historic homes. Wind your way around the fountain across at the Lightner Museum before stopping at the Flagler College campus across the street for a gorgeous architecture fix. If you’re into the city’s (loooong) history, hang out on the grounds of the historic Castillo de San Marcos fort while you take in the view of the bay. There’s a restaurant just about every ten feet in this town, so it’s hard to pick favorites for when all that exploring makes your stomach growl – but consider Columbia, La CocinaThe Raintree CafeThe Prince of Wales, Athena, and The Conch House. If you’re looking for something quick, try the Crave Food TruckBurrito Works, or Schmagel’s Bagels. Unwind at Rhett’s Piano Bar, where you’ll catch live music and delicious cocktails. (There’s a restaurant Scarlett O’Hara’s, because of course! Oh, the charm!). Don’t forget to top it all off by watching the sunset on the water!

Sunset Beach

[Lighthouse image via Flickr]

Email the author of this post at [email protected]