It’s become an annual tradition. Every fall, my family and I—plus a bonus kid to keep my only child company—make the trek down to the Florida Keys to embrace the slower pace and mark the unofficial end of summer. (Unofficial because, let’s be honest, us South Floridians know summer doesn’t actually leave until November.) Once we reach the Overseas Highway, and I spot the pristine blue waters of Key Largo on both sides of the road, my mood palpably changes. I relax. I breathe a little deeper. And, I instantly crave a coconut margarita…
We tend to stay at family resorts in Islamorada (the sandbar alone is worth the trip down, in my opinion), so this year’s visit brought us to the newly renovated Three Waters Resort & Marina, part of the Islamorada Resort Collection. It was named Three Waters because of “its location in the Florida Keys, where the Atlantic Ocean, Florida Bay, and the Gulf of Mexico converge.” Longtime Keys visitors may remember it as the former Postcard Inn. And it’s dog-friendly!
The Resort certainly takes advantage of its three waters views in each of its guest rooms. We had the pleasure of staying in a two queen ocean view balcony room just steps (and a short elevator ride) from Mermaid Beach and Kokomo Pool, or even more importantly: the Lucky Twist ice cream shop. After slipping into our swimsuits, the kids ordered their favorite frozen treats while I was quickly able to satisfy my coconut margarita craving at Kokomo, the only swim-up bar in the Florida Keys.
Three Waters Dining
In fact, you can probably satisfy any craving you have at one of Three Waters’ nine dining options on property. We managed to sample seven of them during our three-day/two-night stay, but if that’s not enough, you can easily hop aboard the Rum Runner, the resort’s complimentary water taxi.
It ferries guests between the three properties in the Islamorada Resort Collection—Three Waters, Amara Cay, and La Siesta Resort & Villas. Not only can you enjoy the restaurants at any of the sister resorts, but the ride itself is a relaxing (free) way to enjoy some time on the open water. These are the main dining options available at Three Waters Resort & Marina:
- Kindler Wood-Fired Fare
The resort’s signature, upscale restaurant featuring live-fire cooking on an open hearth. Expect steak, seafood, wood-fired dishes, and a fine coastal dining experience. It’s perhaps not the most kid-friendly option on property, but we still really enjoyed it. - Little Limón
A rooftop Latin/Asian-fusion concept with bold flavors, small plates, ceviche, oysters, crudo, and sweeping ocean views. It was the perfect place to watch the sunset! - Mercado Morada
A waterfront, street-market style eatery. We enjoyed breakfast here both mornings and the coffee is top notch. - Tiki Bar
Picture Florida Keys–style cocktails and casual bites by the marina, with nightly live music and a laid-back vibe. Fun Fact: the Rum Runner was invented here! - Islamorada Pizza Co.
Don’t sleep on the Caesar salad at this delicious eat-in or grab and go pizza joint. The pies are huge and sharing is highly recommended. - Hideaway (Cove / 21+ area)
Located in the adults-only “Cove” area of Three Waters Resort, it offers lighter fare, cocktails, and healthy options—perfect after a swim or workout.
Three Waters Activities
In addition to customary Keys resort activities such as swimming, biking and snorkeling and water sports like SUP and kayaking, we were eager to try something that the locals are known for: fishing! I booked the girls a private lesson on the dock just steps away from Kokomo Pool (and our gorgeous cabana for the day) and met the famous Patrick from Abel’s Tackle Box.
“If you chum, they will come,” Patrick chanted enthusiastically as he stirred up the waters below the dock. Indeed they did. True (reluctant) beginners, the girls quickly learned how to catch and release fish and had so much fun, despite the fact they had zero interest in throwing them back in the water with their bare hands.
My daughter caught a huge grouper on her first cast, then a few snapper and a needlefish. I honestly enjoyed just watching the whole fishing process play out…coconut margarita in hand, of course. I highly recommend this activity if you’re staying at Three Waters, but it fills up quickly, so make sure to plan ahead.
Note: Fish Like a Local participants must be at least 8 years old to fish and children ages 8-12 must be accompanied by an adult at all times.
Vacation like a Local
Three Waters Resort & Marina is less than a three hour drive from Boca Raton, which makes it a great travel option for a long weekend or a few bonus days off school. We never used our SUV once we arrived on property—it’s completely walkable and we felt extremely safe letting our 12 year-olds wander around on their own.
Proceed at your own risk, though. The girls quickly found the Angler’s Arcade and a Starbucks near the lobby and came back begging for spending money!
Until next fall…
84001 Overseas Highway, Islamorada | 855/868-5172 | marriott.com
Michelle Olson-Rogers is a mom of one and the founder of Modern Boca Mom, a lifestyle website for the stylish and modern South Florida Mommy. She can also be found on Instagram at @modernbocamom. She and her family were hosted by Three Waters Resort & Marina for two nights with a food and beverage credit for review consideration.
