Driving to Key West? Make a stop in Florida’s Upper Keys

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The Overseas Highway in the Florida Keys

When Hurricane Irma roared towards the Florida Keys in 2017, the residents of Key West braced for impact of one of the most powerful storms in Florida’s history, this Category 5 hurricane. But at the last minute, the storm took a slight turn, and Key West miraculously escaped without much damage. It seemed like a miracle, at first.

The other islands in the Keys, the smaller communities along US-1, like Big Pine Key, Marathon, and Islamorada, were obliterated.

Drivers going south on US-1 south from Miami  pass through those small islands, before reaching the famous Seven Mile Bridge and Key West. Perhaps because of the thrill of the drive, or the excitement of reaching Key West, those smaller islands often don’t get noticed. But they have charms of their own, with hotels and restaurants and kitschy spots to get Key Lime Pie.

Related: Is Key West the ultimate spot to spend your winter vacation? You decide.

When Hurricane Irma tore apart those islands, north of Key West, the storm destroyed over 4,000 homes, along with 1,800 boats, and of course many shops, hotels, and restaurants. Every hotel in Islamorada was flooded, and had to close for months, sometimes years, for repairs. And although Key West remained as popular as ever, with big events like Fantasy Fest and Key West Pride bringing in hundreds of thousands of visitors, those visitors just drove by the construction sites withouth stopping, and the islands withered.

After a big facelift, these islands—known as the Upper and Middle Keys—are alive once again: restaurants have re-opened, hotels are filled with guests, and charter boats are zooming around on the water with snorkeling, scuba diving, and fishing trips.

In Islamorada, Cheeca Lodge spent $25 million on its post-Irma renovation, and it is of course very nice, serving guests on the level of major resorts in Key West or Miami. 

There is a lot to see and do in those islands between Miami and Key West. And that includes Kathie Lee Gifford’s favorite restaurant, which we’ll get to later. Here are our Top 5 favorite reasons to stop in the Upper and Middle Keys:


Go snorkeling off the coast of Key Largo

Key Largo’s biggest attraction is John Pennekamp Coral Reef State Park, which includes a large swath of offshore area in the Atlantic Ocean, and protects one of only two living coral reefs in the continental U.S.  Key Largo is the best spot in all of South Floria, definitely, for scuba diving and snorkeling. The coral is not the bright technicolor reef from Finding Nemo, but the big schools of fish are extraordinary. Rays float along the ocean floor, and occasionally a lucky diver will spot a sea turtle. If/when you see a puffer fish, don’t poke it to make it blow up! Leave it alone. 

For the best experience, take a dive charter. They know how to find the best spots with the most fish. Go with Rainbow Reef, which is not an LGBTQ-oriented company despite the “rainbow” name, but they are a delightful bunch.

A note from the environmentalists at Greta’s Gays: Key West passed legislation that bans the sale of sunblocks that contain chemicals that damage coral reefs. All visitors at any beaches anywhere should abide by these rules, as reefs around the world continue to deteriorate due to pollution, and sunblock chemicals are a significant problem. Well at Walgreens Moisturizing Lotion SPF 50 and Hawaiian Tropic Island Sport Ultra Light Spray SPF 30 are two inexpensive reef-safe sunscreens, so bring some on your boat charter with you, and perhaps leave a bottle on the boat for others to use in the future. Even better, wear a shirt while snorkeling, which will block the sun pretty well, and it will also improve the feel of your life jacket, which you should wear while snorkeling because when you see your first puffer fish, you’re going to scream with glee, and choking on ocean water is inevitable.


Feed the tarpon (and the pelicans) at Robbie’s

Sometimes tourist attractions really are fun. Robbie’s is a marina in Islamorada, which has a no-nonsense outdoor restaurant, The Hungry Tarpon, where lunch includes fresh-caught fish—and it’s really caught in Florida, as opposed to some Floida Keys restaurants that import fish from overseas, which is ridiculous. After eating at The Hungry Tarpon, buy a bucket of slimy bait fish for $4, walk down to the end of the pier, and hold a fish in the air over the water. Tarpon jump out of the water and deftly grab the bait fish, although they occasionally try to swallow your hand (photo above, it looks scarier than it really is). The pelicans on the dock are more aggressive than the tarpon, and they will run at you and demand a fish, so be aware of that.


Visit the turtles 

The Turtle Hospital in Marathon cares for injured and rescued sea turtles, and is home to some turtles that are too roughed-up to be returned to the ocean. The facility features an educational visitors center, which has several chances to meet some of the turtles, and it is an interesting, occasionally somber, and entirely heart-warming lesson in ocean conservation. Lots of turtles at the Turtle Hospital are fixed up and returned to the wild, and the cost of admission directly benefits their efforts, so it’s worth a visit.


Get a (locally sourced) beer

The tiny islands of the Florida Keys may seem like an odd place to build a big brewery, but Islamorada has two that are quite good. Islamorada Brewery & Distillery and Florida Keys Brewing Co. provide beer on tap to bars and restaurants around South Florida, as well as bottles and cans to local markets. They both have their own “tasting rooms,” which aren’t fancy, and it’s probably best to sit outside anyway, but they are great places to sample the 40 or 50 varieties of beer that they have on tap. Both breweries are known for their delicious, smooth ales, which are brewed best at warmer temperatures, perfect for Florida. (Lagers, associated with New England, are brewed at colder temperatures.) 

Making beer is particularly advantageous in the Keys: the islands have a clean and clear source of tap water, the Biscayne Aquifer near the Florida Everglades, which is similar to the superb water quality of the many bottled water sources that come from Florida. (That’s right, folks: brands like Zephyrhills and Deer Park are basically Florida tap water.) The rum distilleries in Key West have taken advantage of Florida’s delicious water for many years. And this high-quality water is also necessary for the health of the turtles in the Turtle Hospital.


Go to Kathie Lee Gifford’s favorite restaurant

Kathie Lee Gifford loves Alabama Jack’s, a dive bar and restaurant in North Key Largo, and she has told many stories on her various talk shows about her (slightly tipsy) escapades here. The restaurant is basically a roadside shack, tucked into some magroves on a murky canal, and people in boats come in after a day of fishing and pull up to the little dock for an afternoon of fresh fish and strong drinks. The same band has been playing here for almost 30 years or so, and when the Alabama Jacks clog dancers aren’t doing their thing, Kathie Lee has been known to grab the mic and sing a song or two. And this is all absolutely true! Take a look and listen:


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