When you think of a Florida vacation, what comes to mind?
Distraught families at Disney World? Garish Miami clubs? Mar-a-Lago?
Beyond the “Florida Man” reputation, though, there are pockets of paradise to be found in the Sunshine State. The well-trod Florida Keys were consummate tastemaker Ernest Hemingway’s favored sub-tropical hideaway, after all. And our favorite Florida getaway inhabits an even lesser-known Gulf enclave: the beaches of Fort Myers and Sanibel, a collective of low-key cays and islands that make a right angle with Tampa (to the north) and West Palm beach (to the east).
Below, a detailed itinerary for adventurers and spectators alike, along with the ideal sunset spot for a rum punch that’ll put you to sleep on the beach if you’re not careful. (We recommend packing the SPF 45 for this one. Just in case.)
WHERE TO STAY …
… If your getaway motto is “get away”: Cayo Costa or North Captiva
Both are inaccessible by car, so you’ll have to make your way to these two islands by boat. Cayo Costa is for those looking to go off-the-grid. Shack up at the solar- and propane-powered Eagles Landing — they’ll loan you an ATV to scope out the area’s best fishing.
If you choose the closer North Captiva, hole up in “The W,” an upscale three-bedroom Airbnb with a beach, heated pool and tennis court access — as well as a golf cart to get around. The top of the island features what they call the Salty Approach, a 2,000-foot grass landing strip for anyone itching to take out the Cessna. It’s lined with houses and capped on both ends by the ocean, so it’s not for amateurs. A Captiva Cruises guide will tell you the story of a Christmas Eve crash where the pilot overshot the runway and lost all his family’s presents in the drink.
… If you have a car (and kids): Sundial Beach Resort & Spa
You can’t be faulted for renting a convertible if you’re coming in from greyer skies, but be forewarned: if you race around these parts, you may get a palm tree-sized middle finger from one of the blue-haired locals. Sundial Beach Resort & Spa has suites and activities to accommodate the young’ns while you and the lady do your own thing, whether that’s a bike ride, private boat cruise or 18 championship holes at The Dunes Golf & Tennis Club.
WHAT TO DO …
… If you want to be one with the ocean: Adventure Sea Kayak and SUP
The family-owned business has the makings of a humble rental station, with plenty of kayaks and stand-up paddleboards and (now standard) waterproof bags for phones. But make sure to ask for John Houston, son of the founder, to lead you on a sunset or nighttime tour of Buck Key, a massive mangrove island. His wealth of knowledge about this-or-that hurricane, the local wildlife (which he’ll grab out of the water for closer inspection) and history of the islands is just as thrilling as the dolphins and manatees you’ll likely see.
… If you want to be one with the Green Monster: MLB Spring Training
Fort Myers is the spring training home to the Boston Red Sox and Minnesota Twins. Both the Twins’ Hammond Stadium at CenturyLink Sports Complex and the Sox’s JetBlue Park at Fenway South are about 30 minutes from Sanibel. If you don’t care either way, Fenway South is the better sight to see as it’s a mini replica of its namesake — Green Monster, Pesky’s Pole, the lone red seat and even a manual scoreboard repurposed from Fenway included. Loathe one or both of these teams? Don’t pass up the chance to boo them from a much closer seat.
WHERE TO EAT …
A cold one and your own catch: Lazy Flamingo
Wherever you end up on the islands, the fishing is prime. If you go the hotel route and are at a loss after you’ve caught, cleaned and filleted your catch, bring it over to the Lazy Flamingo. For a few bones, they’ll cook it however you want and throw in some fries and trimmings.
Pirate-level rum punch: Mucky Duck
In theory, English-styled neighborhood “pub” the Mucky Duck is out of place in the island life. In practice, the “English Fish & Chips” is about as British as it gets, with everything from the fresh daily catch to the live Van Morrison covers on the patio. While there’s a wide variety of beer on tap, the trick is to get there 30 minutes before sunset, grab some of their fluorescent rum punch, then stroll out to the adjacent beach to take in the final rays with what seems like the whole island.
More Like This
For more travel news, tips and inspo, sign up for InsideHook's weekly travel newsletter, The Journey.