For day-trippers and travelers who relish stories, architecture and culture, sometimes the biggest rewards are in the smallest cities. Places where modern development hasn’t fully edged out the charm of the past. In Florida, you’ll find those towns from coast to coast. Here are our top picks from Apalachicola in the Panhandle all the way south to Key West.
A trance medium from New York established this spiritualist community in 1894 as a sanctuary away from the northeast winters. Today, it’s still a place where psychics and mediums converge, mainly at the Cassadaga Hotel—which is also more or less the only game in town for having a meal, at its Lost in Time Café, or staying overnight. Wandering the main street, and shopping for crystals and spiritual books is amusing, but to get the most of a Cassadaga day trip, book a session with a psychic, ideally at least a week in advance; a list of mediums can be found on the Cassadaga Spiritual Camp website. On Fridays and Saturdays, free guided historical tours of the town are offered in the afternoon.
Just outside Tampa, Ybor City owes its roots to cigars—and to the Vicente Martinez-Ybor who manufactured them starting in 1885. Today, the district is home to a handful of breweries: Rock Brothers Brewing, Zydeco Brew Werks, BarrieHaus Beer Co. and even a local vodka maker, the Florida Cane Distillery. Of course, the tradition of cigar making is still alive and well. Head to J.C. Newman Cigar Company for a tour of the rolling room and three-level cigar museum, and the chance to take home a few stogies.
Once prominent for orange farming, this hamlet south of Gainesville slowed down following a chilling winter in 1894—so much so that today, Micanopy is referred to as “the town that time forgot.” Visitors today target the town for its antiques, picturesque cemetery and walkable historic downtown clustered around NE 1st Street. Stop by the Old Florida Café on Cholokka Boulevard for a Cuban or Reuben sandwich, then peruse the goods at Ripple Effect Studio and Gallery, the Shady Oak Gallery and Gallery Under the Oaks. Coincidentally, the town starred in the Michael J. Fox movie “Doc Hollywood” but in the movie, it was billed as Grady, South Carolina.
Unlike many of the other Florida towns that made our list, Apalachicola in the Panhandle still derives much of its income now the same way it has since 1850: oysters. This little berg is responsible for 90 percent of the state’s oysters. Today, it still largely lacks pretense, with most of the seafood restaurants favoring simple and basic over high-end and showy. Though not the cheapest of the bunch, Up the Creek Raw Bar has our vote for its on-the-water location and for its fun cocktail menu that includes the City Water, with Cathead pecan vodka and honeysuckle vodka, along with peach liqueur, sweet tea and lemonade.
The French landed on Amelia Island’s Fernandina Beach in 1565, but it was the Spanish in the 1780s that first took full advantage of the island’s harbor—albeit for nefarious means, trafficking slaves along with rum. The U.S. didn’t lay claim to the island until1821, taking it from the Spanish and erecting the still-standing Ft. Clinch. For your own base while exploring the island, consider the 17-room Amelia Schoolhouse Inn, built in 1886 and designed by architect Robert Sands Schuyler. Today, the incredibly well-maintained property merges style, charm and whimsy, honoring its schoolhouse legacy. When exploring the island, don’t miss The Amelia Island Museum of History. The price of admission includes a walking tour, offered daily, that shares the colorful background of this storied place. Ghost tours and pub crawls are also offered through the museum for a fee.
St. Augustine’s Old Town
Hailed as the oldest city in the nation, St. Augustine was once the capital of Spanish Florida—and much of the still-standing architecture reflects that influence. Not to miss is a tour of Flagler College, formerly The Hotel Ponce de Leon. Highlights include the Spanish Renaissance architecture as well as the crystal chandeliers and Tiffany stained glass windows. The 1887-built Lightner Museum—once the Alcazar Hotel—houses a trove of Tiffany stained glass, antiques, sculptures and curiosities. Its lush courtyard, with a bridge and koi pond, is one of the most Instagrammed spots in the city. Stay at Casa Monica Resort and Spa, an updated Autograph Collection property that is itself a historic gem dating to 1888.
Port St. Joe
The Cape San Blas lighthouse, one of the oldest in the state, is one of the more compelling sites—along with the quiet white-sand beaches—of this 1835-established town in the Florida Panhandle. Today, history shows up most in the antique stores, as well as the mom-and-pop businesses, like the handful of Southern diners, that still rule this largely undeveloped beach town.
Birders, bikers, anglers and paddlers are most likely to appreciate Cedar Key, 2 square miles that include a picturesque stretch of weathered bars and restaurants standing on stilts over the Gulf of Mexico. Smack in the middle of town is the most famous watering hole, the Neptune Bar at the Island Hotel. Go in to check out the murals and sip a rum drink. For daytime entertainment, book a birding tour with Captain Doug of Tidewater Tours, or allow him to ferry you along the coast to meet local fauna, from manatees to eagle rays. Or head 5 miles east to Cedar Key State Scrub Preserve, offering 5,000 acres and 13 miles of trails to take on via mountain bike or foot.
Most Sunshine State residents haven’t heard of Waldo, a town that relied on citrus until the late 1800s. Today, it’s the Waldo Farmers and Flea Market that puts Waldo, 20 minutes north of Gainesville, on the map. Open only on Saturday and Sunday, the 50-acre complex showcases the antiques, jewelry, books and other vintage finds of more than 900 vendors. In the town itself, there’s not much by way of official tours, but you can wander by car to see the remnants of the town’s past, including the bright red caboose in the city park.
If it’s your first time to the Conch Republic, surely you put Ft. Zachary Taylor and the home of Old Papa Ernest Hemingway and on your list. For those who’ve been to Key West before, know that there’s more to this 7.2-square-mile than Papa, rum and festivals. Hidden Key West Walking Tours dives deeper into the lore of this eccentric haven, from the boom days when Pan American Airlines based its offices here to the Old Bahama Village neighborhood—plus architecture highlights, famous ghosts, culture and more quirk. As for where to stay, there’s no shortage of storied inns, including The Weatherstation Inn, The Southernmost House, Old Town Manor and the Marquesa Hotel, a refurbished conch house.