Florida has 4,510 islands over ten acres, second only to Alaska, and much of Florida’s attraction and recreation relates to the relationship that Floridians have with their islands.

I thought it would be interesting and perhaps useful to residents and travelers to give awards to my favorite islands of various categories – with a few honorable mentions when I had difficulty making a final selection.

Most Mysterious Island To Visit

 Half way down the Florida Keys on the Bay side is Indian Key State Historic Site.  If you don’t have a boat or canoe or kayak, you’ll have to arrive by tour.  At first it is hard to believe this was once the county seat of Monroe County.

Only The Ghosts Live Now On Indian Key

It was also the home of the ruthless wrecker Jacob Housman and his band.  In the early morn of August 7, 1840, a large party of Spanish-speaking Indians attacked the village, killing 13, including US consul to Mexico Dr. Henry Perrine.  The town never recovered from the absolute destruction and it became a ghost town.  Now all you see are the remains of roads, cisterns, and ruins.

Best Island On Which To Party

We have a tie here.  Once you decide what type of partying you want to do.  If you want a laid-back, casual kind of Caribbean party feel than you can’t beat Key West (Monroe County).  That island could turn into the Venice of America if global warming keeps raising the ocean, but I think the Conchs will continue to build up and party.

Main Street in Key West Is A Party

If you want an international, urban party feeling than Miami Beach has become a global destination during the winter months.  South Beach amazes me for as a college student in the 1960’s the Art Deco district meant great beach, Joe’s Stone Crabs, and a cheap hotel room.

Best Island Beach

 When Dr. Beach and Tripadvisor both name a beach the best in the nation, it must have great sand and clear water.  Siesta Key is a barrier island just south of Sarasota has sugar-white, quartz crystal sand that feels refreshing even if it is July and 95 degrees F.

Sugar White Sand and No Junk At Siesta Key

Also ranked as the fifth best beach in the world Siesta Key is an ideal laid-back family vacation spot with small motels and condos and good restaurants.  The Turtle Beach section is also one of the Gulf’s best snorkel locations.

 Best Island For Surfing

 After seeing dozens of Ron Jon Surf ads while driving to Florida, most visitors assume that Cocoa Beach is the place to surf in Florida.  Well, real surfers are heading further south to Hutchinson Island where 23 miles of Florida’s best surf is found.

Surfer at Dollman Beach

Sebastian Inlet State Park and Fort Pierce Inlet State Park allow camping surfers to have an inexpensive outdoor adventure.  Dollman Beach in Jensen Beach on North Hutchinson is viewed by some as just as challenging.

Most Exclusive Vacation Island

 Certainly Palm Beach is famous for its rich and Presidential palaces and Jupiter Island is loaded with Who’s Who, but I like the idea of leaving Miami Beach by boat and going to Fisher Island.

Fisher Island Is Exclusive

This was once a one-family island of the Vanderbilts until the 1970’s and there have been financial wars for the last few years over control.  Still, you can book a room at the famous Fisher Island resort.  I just looked: Only two rooms left at just $1,375 per night.  At that price, I think some of the island’s past owners like Oprah Winfrey should pay house calls.  The US Census lists no one living below the poverty level here.

My Favorite All-Round Vacation Island

 I love Amelia Island.  You can stay at the #5 in Florida Ritz Carlton on the beach or another beach hotel or one of the island’s incredible Victorian bed and breakfast houses.  There are dozens of blocks of vintage Florida homes and mansions dating from the Civil War to the 1920’s.  On the northern tip is historic Fort Clinch seized by the Yankees in the Civil War.

Floridians (and South Georgians) have discovered the island is a great weekend getaway with boating, fishing, surfing, swimming, and golf.  The number of quality restaurants and bars keep increasing every month although the Palace Saloon remains Florida’s oldest continuous bar.  The state’s oldest hotel the Florida House Inn (1857)

hosted Cuban Revolutionary Jose Marti while he was chased by both Spanish and American agents.

Happy island hopping in Florida!