A Three-Day Escape to Islamorada
Sometimes you don't need a long vacation to feel refreshed. Rebecca and I recently slipped away for a simple three-day getaway to Islamorada in the Florida Keys, and it turned out to be exactly what we needed.
We made the drive down from Cocoa Beach, enjoying the anticipation that builds with every mile as the Overseas Highway begins to reveal the turquoise water and laid-back pace that make the Keys so special.
The trip was filled with memorable culinary pursuits at local restaurants . Our favorite was an unforgettable sunset dinner at the Square Grouper, a place that felt authentic, relaxed, and full of local character. It was the kind of restaurant where you could easily imagine becoming a regular if you lived nearby. We also enjoyed dinner at Flagler Station, which was excellent but a little more upscale than what we were looking for. We wrapped up our culinary tour on night 3 with a meal at Marker 88, another beautiful waterfront spot that perfectly captured the Keys atmosphere. That “Keys” atmosphere included some swarming flies that were only moderately kept at bay by the whirlygig that the locals use on the tables for that purpose.
As enjoyable as the food was, the real highlights happened on the water.
Our first day’s adventure was a snorkeling trip with Captain Kevin of Wild Dolphin Tours. We explored healthy coral formations teeming with marine life. Bonnethead sharks cruised below us while large groupers hid among the reef. Although a few others on the boat were lucky enough to spot sea turtles, they managed to elude us this time. Even without the turtles, the colorful coral and abundance of sea life made for an unforgettable morning beneath the surface.
The following day brought another memorable experience—a leisurely three-mile stand-up paddleboard circuit through the calm waters surrounding Islamorada. The water was so clear that we could watch fish swimming beneath our boards. Then came one of those moments that instantly gets your attention. A four-foot reef shark quietly glided underneath us before disappearing into the deeper water. It was completely peaceful, but it certainly reminded us that we were visitors in a vibrant marine ecosystem.
More than anything, this little trip gave Rebecca and I something that is often hard to find in the middle of busy schedules: uninterrupted time together. Between the paddling, snorkeling, sunsets, and long dinners, we were able to reconnect, slow down, and simply enjoy each other's company.
It wasn't an elaborate vacation or a bucket-list expedition. It was just three days in the Keys—proof that sometimes the shortest getaways create the memories that last the longest.
