1. Gasparilla Island
Sanibel’s surely the best-known west coast barrier island, but Gasparilla offers Old Florida charms and quiet, secluded beaches. Speaking of Old Florida charm, the Gasparilla Inn dates to 1913 and practically drips with the stuff. (This is the west coast of Florida, so of course the inn also offers an excellent golf course.) If the rest of the place isn’t quiet enough for you, try Gasparilla Island State Park, which includes the historic and still functioning Port Boca Grande Lighthouse.
2. Peanut Island
A spot with an unusual 20th-century history in the city of West Palm, Peanut Island is smack in the middle of the Intracoastal, just west of Palm Beach Inlet and east of Riviera Beach. Today there’s some camping and little else; in the 1960s, there was a working bunker for President Kennedy. (JFK needed a place to go in case nuclear Armageddon broke out when he was at the Kennedy winter estate in Palm Beach.) Go for the snorkelling, stay for the Cold War intrigue.
3. Sandspur Island
It’s part of Oleta River State Park, but this undeveloped tropical island in the north end of Biscayne Bay is a world unto itself. Locals also know it as Beer Can Island, which may offer a clue as to the purposes it’s been put to over the years. But it’s also a great spot for kayaking, manatee-watching and just finding a natural Florida escape in the middle of Miami. From the Atlantic, it’s just in from Baker’s Haulover Inlet, west of Haulover Beach and south of the rest of the state park.
4. Nevis Island
The Garfunkel to St. Kitts’ Simon, Nevis is a great destination for an ambitious boat captain looking to do a proper tour of the Caribbean. It doesn’t often get a lot of attention – in the musical Hamilton, when Alexander Hamilton raps about in his early life being “dropped in a forgotten spot in the Caribbean,” he’s talking about Nevis. But for tourists there are worse things than forgotten spots in the Caribbean, and Nevis has plenty to do and see. Charlestown is a quaint and largely preserved colonial town, while Lovers Beach is private, secluded and … well, infer what you will from the name. And yes, you can see Alexander Hamilton’s birthplace; it’s now the Museum of Nevis History.
5. Hutchinson Island
The barrier island in Martin and St. Lucie counties offers all the great beaches, interesting marine life (check out the Florida Oceanographic Society Coastal Science Center) and excellent fishing you’d ever need. But there’s also learning and history on the island. The local-institution Elliot Museum has been around for more than half a century after being founded by the son of turn-of-the-century inventor Sterling Elliott. The quirky museum features everything from early cars to a model circus to what’s purported to be the biggest baseball exhibit outside of Cooperstown. Nearby sits the House of Refuge at Gilbert’s Bar, a 19th-century house of refuge that is the only fully restored one of its kind in Florida.