Islamorada In the Florida Keys

The Lorelei on Islamorada

Islamorada is a lush, tropical paradise surrounded by azure waters.  However, this has not always been the case. A mere 10,000 years ago, the island was a reef. It was part of a reef line which runs from Miami out to the Dry Tortugas. As the global climate changed, Islamorada and the other Keys popped their heads out of the waves and the Keys were born.

The islands were inhabited much later by the Arawak Indians, a fierce and independent Caribbean tribe. They called the island Frank’s Island. Named after a wild-eyed old guy who ran around the island naked yelling at anyone who would listen about how the sharp coral rocks were ruining his clam digger. Rather than listen to Frank, they moved down the Keys to Indian Key, where they lived quietly for years until they took part in a particularly rowdy Bartenders Weekend party, burned down a house and were asked to leave.

Later, the Spanish were traveling along the Keys on their way to conquering the Indians of Central America and stealing all their gold. They stood on the deck of their ship, and as everyone has done since, looking through their glasses of Madeira wine at the sunset they noticed the islands had a particular color.

“Do those islands look purple to you?’

“Sort of.”

“Hold your glass higher.”

“Yeah, now they do.”

“Let’s call them the Purple Islands.”

“That won’t look good on a brochure years from now.”

“How do we say Purple Island in Spanish?”

“Islamorada.”

Had they looked at their charts, they would have seen the island already had a name. Cleveland. But they didn’t, so the name Islamorada stuck.

As your drive down the Keys, you will notice that many of the towns along the Keys have signs with sayings welcoming you to their towns. “Key Largo – If you are too tired to drive farther.” And Layton, “If you blinked, you missed us.” Big Pine Key – Where the Deer Hunter Meet Bambi.” Key West “The End of the Road. No U-Turns.” And of course Islamorada – “Toto, I don’t think we’re in Akron anymore.”

Day's End

Islamorada is now known as the fishing capital of the Keys. Dozens of stores and bars sell T-shirts proclaiming “Islamorada, a quiet little drinking village with a fishing problem.” You can fish the back country, the side of the islands that face the Gulf of Mexico, for tarpon, permit, bonefish and rod busting scallops. Or you can venture out front into the Atlantic to fish for bigger species like sailfish, marlin, yellow tail and the powerful amberjack. A forty-pound amberjack can feel as though it is tied to the bottom with a chain. The jack can pull a 12 year boy, who insisted that he could only catch fish if he uses your Penn International reel and Daiwa rod, and all the gear overboard when it digs for the bottom.

Islamorada is different from most of the Keys. It is not like Key Largo which is a welcome center to the Keys for people driving down from the North.  While the people in Islamorada can party with the best of them, it is not quite the crazy town Key West can be. There is a lot more to Key West than many people realize, but we will cover that in another article.

Islamorada covers seven islands, but that is not apparent when you are driving around. The Hurricane Memorial is here, remembering the people who died in the hurricane in 1935. They also have a library on the island. Not so rare, even for the Keys, but this library has a unique feature. It has its own beach. A real, fully sanded and protected beach. The current between the beach and the mangrove island across from it can be quite swift on tide changes so you need to watch the little ones. You can see the librarian about checking out a book, free wifi access and suntan lotion. Due to budget cuts, the library has reduced operating hours, but the beach is usually open from dawn to dusk and it is pretty quiet.

At the library beach, Islamorada

There are several good restaurants, as there are on almost every Key. Some of my favorites are the Lorelei, pictured at the top of the article and simply one of the best places to watch the sunset, Uncle’s and Bentley’s. There are less expensive choices, such as Islamorada Fish Company and Mama’s BBQ.

Be sure to check out the Diving Museum, even if you’re not a diver. If you just have to shop, try Blue Marlin Jewelers. Handcrafted pieces that will give your credit rating a run for the money, but I have bought a few pieces there for reasonable prices. Take a towel with you so you can wipe up your drool from the counters. Ask for Michelle.

The island is green and usually quiet. Take some time to drive around the back streets. You can’t really get lost. If you have a regular car you can go down all kinds of narrow streets and alleys. If you drive a camper, you’ll have a lot of backing up to do. Just respect other people’s property.

I like Islamorada and its people. After you have gone there a few times, people will get to know you. I like how they call out to me when they see me. “Hey Frank, how’s the clam digger?”

Where to stay:  There are all different levels of motels and hotels to choose from. Three that I am personally familiar with are, The Key Lantern, The Islander and The Cheeca Lodge. The Key lantern is nice. It’s quiet, safe and clean and inexpensive. $39 a night in the off season.  I’ve stayed here quite a bit over twenty years, and apparently have had the same mattress every time. However, for the price, it is hard to beat.

The Islander is a step up in price, but has nice facilities and views of the ocean and a great pool.

Rental bungalow at the Cheeca Lodge

The Cheeca Lodge is top end. Every six months or so they set their tiki hut bar on fire for the entertainment of the guests. OK, not really, but if you know the Cheeca, you know what I mean. Wonderful bar and award winning restaurant inside. The private beach and grounds cannot be beat. If you want to stay for a week or so, check out the bungalows for rent. You’ll never go home.