If you want to know what Key West must have been like back in the Hemingway days, come to secluded Cedar Key, which sits off the Florida coast below the panhandle. This quiet town of less than 1,000 people sits on Way Key, buffered from the mainland by a necklace of marshy, protected islands. The cedar trees in these parts were once used to make pencils, and John Muir spent time here in 1867 while recovering from malaria. Today, though, the locals make their living off a booming clamming industry the smattering of tourists who come to cast a line from the fishing pier or toast the sunset at a watering hole like the Big Deck Raw Bar.
MUST: Paddle along shores of Cedar Key and explore the surrounding islands with Kayak Cedar Keys.
STAY: In one of the cozy cottages at the quirky, quiet Faraway Inn on the edge of downtown, where you can use their kayaks and fish-cleaning station. Starts at $160 per night.
Florida's Best Islands: Siesta Key
You’ll never confuse eight-mile-long Siesta Key, floating off the Gulf Coast below Sarasota and above Fort Myers, with the famed keys south of Miami—and that’s a good thing. This barrier island has long, wide confectionary white sand beaches, the likes of which folks in Key West will only see in their dreams. Though Siesta Key has a definite resort feel, it’s not expensive or overdeveloped, and it's relatively untouched by the Sunshine State's signature blight: millionaire mansions, high-end hotels, and high-rise condos. The best beaches and places to shop and eat are found near the island’s northern tip, in small but bustling Siesta Village. Entertain yourself by fishing, paddleboarding, or kayaking (you can rent equipment from Siesta Sports Rentals).
MUST:The outdoor drum circle that performs on Sunday nights in Siesta Village. STAY:The Capri at Siesta offers low-priced luxury and kitchenettes in each room, just off the beach. Starts at $149 per day.
Florida's Best Islands: Anna Maria Island
Even though Anna Maria Island sits less than an hour south of Tampa Bay, this accessible, family-friendly sand patch feels completely removed from the urban bustle. There’s no McDonald’s on the seven-mile-long island due to strict zoning laws, local ordinances limit buiilding heights to no more than three stories, and free trolleys run up and down its length on Gulf Drive so you can hop a ride instead of driving your car. The result is a pretension-free hideout that’s surprisingly young and vibrant for a Florida coastal island.
MUST: Take the three-hour Dolphin and Manatee Tour led by Adventure Kayak Tours through mangrove tunnels and protected waterways around the island ($55 per person).