visit to the Florida Keys is never cookie-cutter, and, as such, every visitor comes away with their own unique favorites. For our family, Islamorada lives up to its etymology and is our “island home” away from home. It calls to something in the spirit of our family and is one of the favorite vacation destinations for our kids. When we asked our youngest where she wanted to have her fifth-birthday, expecting to hear Orlando, or perhaps the local trampoline park, she answered immediately, “Islamorada.” (True story). As parents that prefer beaches and scuba to theme parks and long lines, this was music to our ears. We’ve apparently raised her right.

Unfortunately, the particular resort that our daughter had fallen in love with, Postcard Inn Islamorada, had had a rough visit from a destructive guest: Hurricane Irma. As of this writing, Postcard Inn is expected to reopen by Fall 2018, but we needed somewhere to go for the spring. Fortunately, the company behind Postcard Inn is also responsible for the nearby sister property, Amara Cay Resort.

For those headed to Key West, Islamorada is the approximate mid-point in their progress through the keys, marking the transition from a tight archipelago to a series of far-flung individual islets. Islamorada is the last of the keys that sit on rock and stone, while those beyond are formed primarily of shifting, but compacted by sand and shell. It’s the kick-off point, the vacation Rubicon, and the last base camp before the wilds take over. Stop on Islamorada and you are standing, quite literally, on the last bit of solid land before the ocean reigns supreme. 

From the moment we set eyes on the hanging wicker chairs in the lobby it was clear that this property had a fun spirit. Gorgeous beach-themed decorations remind you why you came and you are never more than a dozen steps from having your toes in the sand.

Among the best features of the property are the sprawling outside areas, with pool, beach, sandy recreation spaces, fireplaces, wooden lounge chairs and multiple comfortable hammocks where our kids just swung and swung. Our room offered both a beautiful waterfront view, as well as a view of the sports area. Our seven-year-old son spent most of the vacation challenging other guests to games of ping-pong or basketball. If the sun got the best of mom and dad, we could watch from our room’s porch while our son became the reigning champion of the bean bag toss.

A further kudos goes to the staff at the Amara Cay Resort for their attentiveness to our family. As we made our reservation, they asked if we were celebrating a special occasion. As a result, we arrived to find our room festooned with “Happy Birthday” decorations, snacks, and small gifts for our bubbly birthday-girl. It actually convinced her that the entire resort was there to help her celebrate, so from that point forward every person we passed in the hall, rode the elevator with, or simply met in the lobby was greeted by a tiny voice chirping, “It’s my birthday!”

The Amara Cay offered a delightful opportunity for both of our children to run and play, while mom and dad recuperated. We made full use of the clustered seating arrangements that populated the sand.  Especially lovely for us were the circled Adirondack chairs positioned just close enough to the recreation lawn for us to watch the kids, but far enough away to give us space to relax and them room to feel unrestrained. The trip also benefitted from fortunate timing. I had recently made the acquaintance of Don Bruns, a Sarasota, Florida-based mystery author whose novel, Too Much Stuff, is set on Islamorada. Mr. Bruns insisted that I take a copy of the excellent historical novel, Last Train to Paradise by Les Standiford, with me to the keys. The tale of how Henry Flagler walked away from his partnership with Rockefeller to build “impossible” projects was enthralling.

Southern Florida, and the Keys, in particular, offered construction and location challenges that outstripped the technology of the times. Flagler turned his incredible wealth and unhesitating drive to building a railway to Key West. Much like JFK’s “moon-shot” commitment that would come 50 years later, Flagler began building a railroad in the 1890s with no answer as to how it could be done. No one knew yet how to cross the extended stretches of open waters, or how to build permanent structures on the soft seafloor.

As you may know, Flagler’s overseas railroad, once completed, was a “golden age” marvel. Tragically, it only persisted a few decades before Mother Nature washed it away in 1935. The last train ever to travel south on the tracks, steam locomotive #447, was sent on a rescue mission. They made it as far as Islamorada before the rising waters pushed all eleven coaches off the rails, leaving only the locomotive standing. The more recent damage from Hurricane Irma, which you can still see from US Highway 1, gives the history extra gravitas.

Of course, I also brought a copy of Don’s own fiction novel, Too Much Stuff. It was fun to parallel the adventures of his duo of quirky, bumbling detectives-in-spite-of-themselves, on their journey to Islamorada. A clever bit of speculative fiction puts the heroes on a hunt for a lost golden treasure that the Mr. Bruns imagines might have been on that final train. Geology, hurricanes, and great stories both fact and fiction came together to enhance and enrich what could be seen as a simple vacation stop. I heartily recommend both books, especially if you are planning a trip to the Florida Keys.

On-premises at the Amara Cay, we found ourselves mostly eating outside, typically under the thatched roof of one or another of the many tiki huts. The Smoked Fish Dip was a big hit with the whole family, and I may have eaten more Grilled Honey Habanero Wings than is advisable, but I regret nothing. The kids loved the Sliders burger plate.

The Amara Cay Resort has great access to other nearby destinations. The MoradaWay Arts & Cultural District is only a couple of blocks long which meant that the small street festival we stumbled upon was a cozy, friendly stop. The Florida Keys Brewing Co. blends island culture and brew culture perfectly.

Leave an evening free to eat at the outdoor Lorelei Restaurant and Cabana Bar. The restaurant has a deck, as well as plastic tables and chairs spread over a thin beach-covered isthmus. Arrive early and squat a table so that you can enjoy the sunset with sandy feet. A sunset dinner at Lorelei offers the sort of vacation experience where the memories outlive the details. The service, the seating, and even the food were all good, although not gourmet, but that didn’t matter, our family will make this an Islamorada tradition.

Also, leave time to visit the Theater Of The Sea marine mammal park. This fantastic facility brings you up-close to performing dolphins in a way that no large park could do. Interestingly, Flagler’s fingerprints live on here as well, as the animals’ pools are the remains of a railroad rock quarry.

Theater Of The Sea offers amazing individual experiences too. Our daughter celebrated a birthday like no other. A pair of dolphins sang a chirpy version of “Happy Birthday,” and later she held a canvas while a different dolphin painted colorfully on it with a brush.

Back at the resort, on the beach, the kids each ran about with a slider in one hand. They spotted an enormous wild iguana on the seawall. The lizard jumped in the ocean to swim away. Our kids were so excited that they may as well have been exploring the Serengeti. Meanwhile, my wife and I clinked our cocktails, before I returned to reading that mystery novel. I needed to find out how it ended! For us, we had already found our Islamorada treasure.