Five Funky Florida Towns
No High-Rise Condos Here
While much of Florida is overdeveloped, it still has old-school, funky towns tucked between the theme parks and oceanside high-rises. In these pockets, you’ll find pastel cottages instead of luxury towers and mom-and-pop seafood eateries instead of chain restaurants. Mermaids and mediums, too. Here are five such places.
Matlacha
On Florida’s southwestern coast, quirky Matlacha completely covers a little island that sits between Pine Island, which is Florida’s largest island, and the mainland where Fort Myers is located. It is a cute, artsy fishing village with quirky cottages and bungalows packed tightly together along canals. There is no true downtown, but there are brightly painted boutiques, fun art galleries and ramshackle seafood shacks scattered about. Matlacha also has a lot of Hookers (women who wear hooks in their shirt pockets and are members of a civic group that sponsors fundraising events).
Gulfport
Along Boca Ciega Bay on the Gulf Coast, Gulfport is just west of St. Petersburg and is known for its Old Florida waterfront district and artsy, bohemian vibe. Homes are mostly modest concrete block style while canal-front homes are generally gorgeous and have a boat slip. Beach Boulevard is lined with one story buildings that house colorful restaurants, interesting shops and comforting bookstores. Art walks happen on the first Friday and third Saturday of each month. The pastel green Gulfport Casino Ballroom sits next to the water and offers anything from Argentine tango to Salsa five nights per week (although it is currently closed while working to repair recent hurricane damage).
Weeki Wachee Area
Weeki Wachee, North Weeki Wachee and Weeki Wachee Gardens are essentially one community with a retro vibe about an hour north of Tampa and south and east of the Chassahowitzka Wildlife Management Area, which is adjacent to the Gulf of Mexico. The area grew up around the famous, slightly cheesy Weeki Wachee Springs tourist attraction. This synchronized underwater mermaid show began in 1947 and reached its heyday in the 1950s and 1960s. These days, vacationers come still come, not just to see mermaids but also to kayak and canoe along the incredibly blue Weeki Wachee River. Somewhat haphazard neighborhoods with older ranch ramblers mingle with new, well-tended custom home subdivisions.
Key West
The southernmost city in the continental U.S. is famous Key West. Its funky Caribbean vibe draws “snowbirds” and tourists from around the world, and shorts and t-shirts almost count as formal wear. Free-roaming roosters, drag shows, Ernest Hemingway lore and sunset parties every night make this a lively place. Duval Street often takes on a carnival atmosphere in the evening and is home to colorful shops, famous pubs and storied eateries, including Sloppy Joe’s and Rick’s Bar. Key West is also famous for its colorful historic mansions, bungalows, shotgun homes, Conch houses and homes with eyebrow windows and deep porches, many on a small lot with untamed vegetation.