We kicked off our “Island Hopper” series a few months ago, and we’re back with our third article in the series. As a refresher, we’re introducing you to some of the many island destinations located right here in the Southern United States, a region that is lined with literally hundreds of islands, each with their own unique personalities.

Make sure to check out our first two articles, which covers Florida’s First Coast, and the Alabama Gulf Coast and the Florida Panhandle, and then follow along as we take a tour of island destinations from the white sands of Dauphin Island in Alabama to the historic beach at Kitty Hawk where the Wright Brothers took their famous first flights. Hopefully you might even find a new favorite vacation destination!

Florida Keys

The pace of life is slower in the Keys, where people treat the everyday event of a sunset as a reason for a party. Image: Bob Krist/Florida Keys News Bureau

If the chill of winter is getting you down, here’s a stat that might grab your attention: the temperature in Key West has never gotten below 40 degrees in recorded history. In case that implies that it must have a nasty, hot climate, the high temperature has actually exceeded 100 degrees only three times in a century. Heck, you can reach both those extremes in the same month in Nashville or Birmingham!

The lovely climate is just one reason why the Florida Keys are such a popular destination and why you should consider adding them to the itinerary for your next island adventure. First off, this 130-mile-long string of 40+ islands is indeed technically keys (or cayes,) which means a subset of islands that are low elevation piles of debris that form on top of coral reefs. That doesn’t make them any less inviting, although the complex ecosystem between the ocean and the reef makes them vulnerable to natural elements like wind and waves. It’s also why you’ll encounter mangrove forests and swamps on many of the keys, since the intertwined roots of the trees help hold everything together and act as a natural seawall.

Another important thing to note before planning a trip is that you shouldn’t be in a hurry to get anywhere in the Keys. While many tourists think that Miami is near the tip of Florida, if you rent a car at the Miami airport, you’ll drive at least an hour and a half in fairly heavy traffic across the southern end of the peninsula through Homestead before you even reach the first Key in Key Largo. And it’s not an exciting drive until you actually reach the first bridge off the mainland. Another option is to fly straight into Key West, but then you would miss the drama of the trip down US 1 along the highway where, in the early 20th century, railroad baron Henry Flagler completed an extension of his Florida East Coast Railroad from Miami all the way to Key West. The narrow highway often leads to a slow trip down the Keys, but what’s your hurry? Take in the scenery on the trip to Key West from the Miami airport and figure out where you want to stop a spell on the drive back. Keep an eye out for the mile markers along the side of the highway, because that’s how most locals give directions. Here are some of the highlights you might encounter along the way.

Key Largo

Key Largo is, as its Spanish name implies, the longest of the Keys and prides itself as being one of the scuba diving capitals of the world. It is home to the world’s largest artificial reef, the intentionally scuttled 510-foot USS Spiegel Grove and the nation’s first underwater park, John Pennekamp Coral Reef State Park. Whether you snorkel, scuba or just take a ride out on a glass-bottomed boat, the clear water and beautiful coral are stunning, and the underwater statue of Jesus is a popular photo site.

Visitors of a certain age might remember “The African Queen,” the classic Bogart and Hepburn movie. The actual steamboat from the 1951 movie has been fully restored and runs canal tours and dinner cruises. It’s like taking a ride into the glamorous past of Hollywood!

A meal at Mrs. Mac’s Kitchen is a staple of any visit to Key Largo. The oldest restaurant on the island, Mrs. Mac’s serves delicious seafood dishes, and their classic conch fritters are a mandatory order. SB TIP: There are two Mrs. Mac’s on Key Largo. The more charming original location is near Mile Marker 99.4.

If you decide to stay on Key Largo, check out Bungalows Key Largo, a 12-acre 135-unit luxury inclusive resort that is the island’s first all-inclusive resort, which features a Zen Garden Spa, two in-ground pools, a fitness Tiki hut, 1,000 feet of shoreline and multiple dining venues including Bogie & Bacall’s, Sea Señor, Fish Tales and two on-site bars.

Another option is the nation’s only undersea hotel, Jules’ Undersea Lodge, located 30 feet below the surface. Guests can earn their scuba certification at the resort or just enjoy watching the aquatic life swim by.

Under the sea and eminently Instagrammable! Image: Stephen Frink/Florida Keys News Bureau

You can still imagine Bogie at the helm. Image: Andy Newman/Florida Keys News Bureau/HO


The next major stop on the drive south is Islamorada, Spanish for “purple island” perhaps for the beautiful bougainvillea that grow on the four keys and two secluded small islets that make up the key. It is widely known as “The Sportfishing Capital of the World,” with multiple charter boats available to take you out fishing for sailfish, marlin, dolphin (the fish, not the mammal), kingfish, snapper, barracuda and grouper offshore in the ocean along with tarpon, bonefish, permit, redfish and other species in the shallow coastal waters.

If you prefer to get up close and personal with fish without leaving dry land, drop by Robbie’s, where you can hand-feed massive tarpon. These prehistoric-looking fish thrash around during feeding, but don’t worry. They are well-trained and harmless. Robbie’s also features a great bar and seafood restaurant along with shops filled with potential souvenirs and tour companies that will take you out fishing, jet skiing, snorkeling or parasailing.

Another fun stop is Florida Keys Brewing Company (FKBC), the first craft brewery in the Upper Keys. Starting out with a tiny brewing system that was barely bigger than a homebrew set-up, FKBC has added a much larger production brewery to supply their delicious beers up and down the Keys. Stop by their cozy taproom to see what they are pouring.

No trip to Islamorada is complete without at least a quick stop to see Betsy the giant lobster. And we do mean big because Betsy is almost 30 feet tall and 40 feet long. The fiberglass statue marks the entrance to the Rain Barrel Artisans’ Village, a collection of shops and galleries that would be worth visiting even if there wasn’t a giant crustacean to draw you in.

Get ready for the fight of your life if you hook into a big one off the shore of Islamorada. Image: Andy Newman/Florida Keys News Bureau

You’re gonna need a lot of butter for a lobster as big as Betsy. Image: Bob Care/Florida Keys News Bureau


Marathon marks about the halfway point in the four-hour drive from Miami to Key West. Marathon is actually a 10-mile stretch of several islands that represent the Middle Keys. Still clinging to the old-school fishing village heritage of their past, Marathon is a family-friendly destination. This is especially true at two attractions that are great for kids, Florida Keys Aquarium Encounters and the Turtle Hospital. At the former, visitors can snorkel in a coral reef tank or pet tame stingrays and sharks. The Turtle Hospital is a non-profit facility dedicated to the rehabilitation of sea turtles and the education of the public about these beautiful aquatic animals.

If you’re a gephyrophobic (someone with a fear of bridges,) you might want to brace yourself for the trip across the famous Seven Mile Bridge. Actually, there are two bridges that were once part of the original railroad line, and it was one of the longest spans in the world when it was constructed. Connecting the Middle Keys with the Lower Keys, Seven Mile Bridge offers sweeping views of the beautiful turquoise waters and offers the chance to make a quick pit stop at Pigeon Key. The tiny 5-acre island was once a camp for the workers who built the bridge and is still home to eight buildings on the National Register of Historic Places.

It’s tough to keep your eyes on the road while crossing this man-made miracle. Image: Andy Newman/Florida Keys News Bureau

The Lower Keys

As Highway 1 turns west after the bridge, you enter the Lower Keys, a series of islands that are home to two national wildlife refuges, a national marine sanctuary and a state park. With an emphasis on preserving the natural beauty of the area, the Lower Keys are more rustic than their neighbors up and down the highway. Lodging options tend toward family-owned resorts, RV parks and campgrounds with plenty of charming little restaurants as dining options.

Perhaps the most renowned resident of the Lower Keys is the endangered Key deer that is only found in this region. A subspecies of the more common white-tailed deer, Key deer are much smaller, about the size of a large dog. Hunted to near extinction by the middle of the past century, the herd has been managed by wildlife experts to where there are an estimated 700 left on the islands. Your best chance to spot one would be on Big Pine Key, home of the National Key Deer Refuge.

The Lower Keys are still reminders of the rugged history of the region before the highways came through. Image: Andy Newman/Florida Keys News Bureau

Key deer look like they would make great pets, but please keep your distance from these wild creatures. Image: Andy Newman/Florida Keys News Bureau

When most people think of the Florida Keys, it’s Key West that comes to mind, with good reason. The eclectic community is home to a population of quirky residents who call themselves “Conchs” and cling fiercely to the independence of “The Conch Republic,” their mythical micro-nation, which occasionally declare themselves to be separate from the rest of the United States. Known for the nightlife, especially along the main drag, which gives its name to the “Duval Crawl” itinerary of bar hopping, the bars and restaurants of Key West exude the sort of laid-back vibe and live music made famous by Jimmy Buffett and his legion of Parrotheads.

Take a ride on the Key West Conch Train for a tour of some of the historic sites of the 2-mile-by-4-mile island. The trolley makes stops at famous local attractions like Mallory Square, the Key West Shipwreck Treasure Museum and Flagler Station, the original terminus of the railroad line.

Plenty of visitors come to Key West by boat thanks to the ample anchorage in the harbor. Image: Andy Newman/Florida Keys News Bureau

For a natural bit of Key West’s “local color,” check out the Key West Butterfly and Nature Conservatory, where you’ll stroll through a giant space filled with brilliantly colorful examples of more than 50 species of butterflies flitting about under a climate-controlled, glass enclosed habitat. Additionally, the Conservatory also houses 20+ species of exotic birds sharing the tropical trees in the transparent enclosure. (Hopefully they don’t eat butterflies!) The family-friendly attraction also contains a Learning Center, a gift shop and a gallery called “Wings of Imagination” showcasing the butterfly-themed work of a local artist.

While some might argue for Jimmy Buffett, the most famous resident of Key West has historically been acknowledged to be Ernest Hemingway. You’ll see “Papa’s” image everywhere, and the annual lookalike contest draws bearded competitors from around the world.

You can visit Hemingway’s Home to see where the famous writer lived for decades during the early 20th century. One fun piece of his history that still lives on in Key West is of the feline variety. A ship captain once gave Hemingway a rare six-toed tomcat, and his progeny can still be seen roaming the grounds of the Hemingway House and Museum as well as occasionally walking Duvall Street downtown. Speaking of wildlife, hundreds of chickens also run free all over Key West. Perhaps they are the reason that all those cats stick around.

The Key West Butterfly and Nature Conservatory is fun way to spend an afternoon in Key West. Image: Ashley Haugen

It’s okay to be gray for this beauty contest. Image: Rob O’Neal/Florida Keys News Bureau/HO

Hemingway’s home is an excellent example of tradition colonial Spanish architecture. Image: Laurence Norah/Florida Keys News Bureau

Chickens are everywhere — even in the souvenir shops! Image: Ashley Haugen

Many bars in Key West claim to be Hemingway’s favorite haunt, but to be truthful, he spent time drinking in a lot of places. The most well-known are Sloppy Joe’s and Captain Tony’s, said to have been the inspiration for a bar Hemingway called “Freddy’s” in his book To Have and Have NotBlue Heaven can boast that Hemingway used to referee Friday night boxing matches in the restaurant’s courtyard. They don’t fight anymore, but the seafood is spectacular, particularly any dish with scallop sauce.

There are two Key West destinations that almost every tourist makes a point of visiting, and with good reason. The first is Fort Zachary Taylor Park. Not only is the presidential park home to a restored pre-Civil War-era fort that has been designated as a National Historical landmark for its significant role in the early history of Florida as a state, but the park also features a public beach with cabana and chair rentals, easy access to snorkeling and fishing opportunities and a quaint cafe to grab some shade and a sandwich during a day of beach time. It’s also close to the home of the literal end of the road, the southernmost point in the United States. Marked by a large colorful painted buoy, it’s a very popular photo op for Key West visitors wanting to prove that they’ve been within 90 nautical miles of Cuba.

Blue Heaven is nothing fancy, but the food is fabulous, and they have live music and games for guests of all ages. Image: Ashley Haugen 

For the best sunset view in Key West, head to the rooftop bar of the La Concha Hotel. Grab a cocktail and say goodbye to another beautiful day in the Keys. Image: Ashley Haugen

The second locale that seems to show up in every Instagram feed is Mallory Square, a popular gathering spot for locals and visitors to watch the sunset while being entertained by jugglers and tightrope walkers. But really, the colors as the sun dips below the ocean are entertainment enough.

When you’re ready to book your Florida Keys getaway, start your planning at fla-keys.com.


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