When planning this year’s family vacation, I wanted a laid-back Florida beach escape requiring just a few hours behind the wheel. It was the perfect excuse to return to one of my favorite destinations: The Florida Keys. Our family is no stranger to the Keys; we’ve explored the beaches of Key Largo and the chaotic charm of Key West. But we had mainly just driven through Islamorada, the heart of the Middle Keys. This time, we decided to book a stay at Three Waters Resort & Marina in Islamorada, an oceanfront resort that served as our anchor for a three-day family escape.
Day 1: High Tides and Tiki Bars
Our trip began with an early afternoon arrival at Three Waters Resort. The property spans 15 acres and features a classic Florida Keys design with open-air corridors. Though I had my kids in tow, if you’re looking for a grown-up vacation, the resort also includes an adults-only waterfront retreat, The Cove, which features an adults-only pool, fitness center, and restaurant.
After checking into our spacious oceanfront suite (which immediately won points for its beachy, modern decor), we decided to drop our bags and explore the grounds. We kicked off our vacation at the resort’s massive oceanfront pool deck. While I staked out a spot on a beach lounger under an umbrella, my teens wasted no time jumping into the pool, which was a major magnet for families on-site.
For dinner, we headed to the legendary Tiki Bar, located by the resort’s marina. The Tiki Bar is actually a piece of Florida Keys history; it opened in 1969 and is recognized as the first official tiki bar in the Florida Keys. It’s also the birthplace of the rum runner cocktail, invented by bartender “Tiki John,” who mixed light and dark rums with banana liqueur, berry, and citrus.
Sitting under the restaurant’s thatched roof with the Atlantic breeze kicking up, we dug into plates of fish and chips and coconut shrimp. Before returning to our room, we made a quick detour to Lucky Twist, the resort’s nostalgic ice creamery, for soft-serve waffle cones.
Day 2: Feeding Tarpon and Ocean Cruising
Wanting to fuel up for a day of adventures, we headed down to the resort’s breakfast restaurant, Kindler Wood-Fired Fare. Breakfast at the upscale restaurant included comfort dishes like Bananas Foster French Toast and Cinnamon Roll Pancakes, which provided the perfect morning jumpstart.
By 10:00 AM, we were on our way to Robbie’s Marina, an iconic attraction located just a few miles down the road. Robbie’s is most famous for the massive Atlantic tarpon that gather under its wooden docks. After buying bait from the tackle shop, we walked out onto the piers, and my kids experienced the thrill of hand-feeding the hundred-pound fish.
By midday, we returned to Three Waters to take advantage of one of the resort’s coolest perks: the Rum Runner Water Taxi. This complimentary resort boat shuttle takes guests to Three Waters’ nearby sister properties, Amara Cay Resort and La Siesta Resort & Villas. Even though we stayed on board the water taxi, we enjoyed the scenic cruise along the coastline.
After lunch from the poolside Kokomo (pineapple skewers and cold-water lobster rolls), we decided to take advantage of the resort’s complimentary water sports. The resort offers daily kayak and stand-up paddleboard rentals, and for a fee, guests can rent jet skis, two-person catamaran boats, and floating docks with seating for two. My son and I grabbed a kayak and spent two hours paddling around the resort, wading through a few feet of typical Florida summer seaweed before hitting open water.
After a demanding afternoon on the water, dinner needed to be effortless. We found our answer at the Islamorada Pizza Co., a retro indoor-outdoor pizzeria that serves hand-tossed artisan pies. We split a Key-Waiian pie (topped with pineapple, bacon, and feta), and then played a round of corn hole under the stars.
Day 3: Sunken Treasures and a Sandbar Party
For our final day, we wanted to explore one of the area’s local museums. After grabbing a quick breakfast, we drove less than five minutes up the Overseas Highway to the History of Diving Museum. The interactive exhibits walk you through thousands of years of man’s attempt to breathe underwater, showcasing a collection of historic brass diving helmets, ancient scuba gear, and genuine sunken treasure recovered from local shipwrecks.
After our museum visit, we booked a three-hour Snorkel and Sandbar Combo Adventure excursion with Spray Watersports, which started with a sailing to Islamorada’s famous Alligator Reef Lighthouse. My kids and I strapped on our snorkel gear and spent about an hour exploring in the warm, tropical waters. Our second stop was the Islamorada Sandbar, where dozens of boats were docked. We waded through waist-deep water and stretched out on the floating loungers, taking in the views.
Our final evening called for a celebratory dinner, and we found it at Mercado Morada. The Central American-inspired restaurant serves comfort food like tropical shrimp tostados, tamales, and chicken mole tacos, and the bonus was watching the gorgeous sunset behind us as the day came to a close.
After checking out the next morning, we stretched out the vacation with a few final stops on the drive home. Our first stop was Rain Barrel Village, a quirky open-air artisan market famous for “Betsy,” the iconic 30-foot-tall roadside Florida spiny lobster sculpture that greets guests at the entrance. We spent an hour wandering through local art galleries and browsing the handmade souvenirs.
We also made time to stop by for one of the Keys’ most famous desserts: Key Lime Pie. Located about 15 minutes north of Islamorada, the Blonde Giraffe Key Lime Pie Factory serves Key Lime Pie by the slice, topped with meringue or whipped cream, or dipped in chocolate. We enjoyed a refreshing slice in their garden setting, the sweet ending to our family vacation.
Back on the road, I realized that our three days in Islamorada had given us exactly what we needed. Thanks to the activity-packed itinerary, we experienced the adventurous spirit of the Florida Keys, while the luxury of Three Waters Resort allowed us to enjoy the laid-back vibe the Keys are known for.
