Life is an island highway.

Island hop till you drop.

When you strip away the omnipresent Disney and admittedly-pretty-funny Florida Man stereotypes that plague the Sunshine State, you just might see America’s southeasternmost extremity for what it really is: a subtropical-to-tropical paradise. Here you’ll find 1,350 miles of convivial coastline, an effervescent ecosystem teeming with nature not found anywhere else in the States, and a melting pot of (not all gray-headed) thalassophiles blissed out on the salt life.

If you think of the state as an eastern-oriented leg, Fort Myers is the Achilles tendon of Florida. And its tempting attractions have found our soft spot. Almost directly between Tampa and Everglades National Park, the city is surrounded by islands. From Pine Island to Sanibel Island, Cabbage Key, and Cayo Costa, this southern part of the Gulf Coast shines with teal waters, laid back restaurants, and sleepy beaches.

It’s not super well known, but if it were, that would be because of its world-class sea shelling, its Caribbean-esque beaches, or perhaps even its blossoming beer scene. Here’s how to get the most out of a trip to this underrated sliver of the Southeast.

You could just kayak to every island. | Photo courtesy of Visit Fort Myers

Kayak through mangroves on Pine Island Sound

Florida’s Southwest coast is home to one of the largest mangrove swamps in the world. These leggy, aquatic trees make up entire islands speckling the body of water known as the Pine Island Sound. Along the aquatic preserve separating Pine Island from the outer islands of Sanibel, Captiva, and Cayo Costa, pockets of life are explorable only by canoe and kayak.

The tour operator Gulf Coast Kayak launches from the colorful town of Matlacha and leads visitors along a portion of the famous 190-mile Great Calusa Blueway paddling trail. Under their guide, the boats head into isolated labyrinths of twisty tree roots. Inside the mangrove tunnels lives an oasis of fauna: oysters, barnacles, wading birds, federally threatened American crocodiles (not to be confused with more common American alligators), and, sure, a few thousand saltwater mosquitoes that literally nobody asked for.

The wildlife is most active at dawn and dusk, when temperatures are cool and the water is quiet. But beware—these are peak mosquito and no-see-um times. Consider bathing in (hopefully natural) bug repellent before taking to the Sound.

This is just one stop on the ale trail. | Photo courtesy of Visit Fort Myers

This is just one stop on the ale trail. | Photo courtesy of Visit Fort Myers

Sip craft beer in Fort Myers

Not many make the pilgrimage to Florida just to try its beer. For starters, the hot, muggy climate is suboptimal for growing hops—but that isn’t to say Southwest Florida brewers haven’t taken on the challenge. Crazy Dingo sits on a small farm and sources the Cascade hops for its pale ales from its own backyard, claiming to be the southernmost hops grower in the country (take that, PNW).

Lee County, surrounding Fort Myers, is the centerpiece of the Southwest Florida Ale Trail, claiming 13 of the route’s 21 brewery locations. Other ale trail establishments besides Crazy Dingo include Fort Myers Brewing Company, the first microbrewery in the county; Point Ybel Brewing Company, applauded for introducing the region’s first sour ales; and Millennial Brewing Company, beloved as much for the fun atmosphere as for the beer.

And if breweries aren’t your vibe, opt instead for a hibiscus-topped hurricane cocktail at one of the region’s dozen-plus tiki bars.

Dare you to count the seashells. | angela auclair/Moment/Getty Images

Dare you to count the seashells. | angela auclair/Moment/Getty Images

Admire the seashells on Sanibel Island

There’s possibly nowhere in the world better for a beachcomber than on Sanibel Island after a storm. Something about the island’s unusual east-west orientation combined with the slope of the seafloor and the gentle current make it a bonafide treasure trove of seashells. More than 400 varieties have been found here, according to Sanibel’s Bailey-Matthews National Shell Museum, the only museum in the US “devoted solely to shells and the living mollusks that create them.”

The museum itself contains some 500,000 shells and aquarium displays to accompany them, but one must admit: Spotting sundry exoskeletons in the wild is slightly more exciting than seeing them hung on a wall.

Here’s how the locals say to do it: Go to either end of the island—specifically Lighthouse Beach Park, Blind Pass Beach, or Bowman’s Beach—an hour before or after low tide. Then look at the surf line and debris line for intact angulate wentletraps, calico scallops, rose petal tellins, dwarf arrow tritons, and more. The shelling is best in November through April, especially after a storm.

While it is legal (and in some places even encouraged) to take shells from Florida beaches so long as there’s nothing living inside them, principle No. 4 of Leave No Trace says to “leave what you find.”

This is the money shot. | Photo courtesy of Visit Fort Myers

This is the money shot. | Photo courtesy of Visit Fort Myers

Eat paradise-level burgers on Cabbage Key

One of the most peculiar restaurants you’ll probably ever dine in sits on its own island spanning 100 acres of practically undeveloped land. Located just off Pine Island, it’s accessible only by boat, and it shares a name with the island itself. Cabbage Key the restaurant contains thousands of dollar bills taped to the walls and ceiling. The permanent markers hanging out of servers’ aprons encourage diners to leave their mark. (If your dollar falls, it gets donated.)

In the “money room,” you can tuck into what’s widely considered to be the original Cheeseburger in Paradise, while wild tortoises cruise walking paths below. The restaurant doubles as an inn and is joined on the island by seven cottages that, yes, you can rent if you’re worried about getting stuck on the island.

Bear in mind that staying on Cabbage Key could mean spotty cell service and special attention to water consumption. Rest assured, claiming a slice of this remote paradise for a night is well worth it.

Some pretty peaceful island hopping on Cayo Costa. | Photo courtesy of Visit Fort Myers

Some pretty peaceful island hopping on Cayo Costa. | Photo courtesy of Visit Fort Myers

Escape the crowds on Cayo Costa

Folks flock to Florida’s Gulf Coast like birds to marshland. Despite its Achilles tendon being somewhat of a “hidden gem,” Lee County beaches attract some 5 million tourists a year.

But on the remote island of Cayo Costa, 2,426 acres of unspoiled State Park land, you won’t find beach umbrellas or ice cream stands or much of anything besides driftwood and a few other families who arrived by watercraft. This island is accessible only by boat (or private plane, if you happen to have one). All it contains is a primitive campground and a couple dozen tucked-away mansions.

The vibe is deserted island. The wildlife: sea turtles, manatees, dolphins, shorebirds, raptors. The water: sparkling turquoise.

You could rent your own boat at Jensen’s Marina on Captiva Island or take a water taxi to Cayo Costa, but then you wouldn’t get the experience of traveling with a local. Brian Haloway, also known as Captain Brian on the Water, has been toting tourists across the Sound since the ’90s and can identify a bird’s sex as it’s flying—he’s that good.

Ask him to swing by Hemp Key while you’re at it. The seven-acre Critical Wildlife Area is a rookery for double-crested cormorants, blue heron, frigatebirds, and egrets.

(Oh, you like birds? Catch the roseate spoonbill and other avian action at J.N. “Ding” Darling National Wildlife Refuge on Sanibel Island. Also, use its award-winning bathrooms. As Supervisory Refuge Ranger Toni Westland says, “you haven’t peed until you’ve peed at ‘Ding’ Darling.”)

This post by Olivia Young featuring Cabbage Key originally appeared on