Private Seaplanes and ‘Rum Runner’ Rides: This Islamorada Resort Opens Doors to the Florida Keys

I arrived at the Venetian Marina and Yacht Club in Miami, Florida, five minutes late for a chartered flight and noticed I was the only one there, other than a pilot waving back at me. Upon shaking his hand, I asked, “Am I the first one to arrive or the last?” He shook my hand back while smirking. “Both! It’s only you today.”

We took a small boat out to the middle of Biscayne Bay, the body of water between what I call “the mainland” and Miami Beach.

“It’ll be here any minute,” the pilot said. I looked around and glimpsed a small plane in the distance, gradually approaching — not quite an airliner, not quite a helicopter, this was a seaplane courtesy of Miami Seaplane Tours.

Photos: Keven Gungor

The seaplane made a smooth landing nearby, and the pilot ushered me aboard. I cosplayed as Tom Cruise for the next 45 minutes — Top Gun headset and all — as the aircraft made its way down to the Florida Keys so I could check out Three Waters Resort & Marina, which opened its doors in October 2024.

Before I knew it, we’d touched back down, directly on the sands of the resort’s beach, and my visit to Three Waters (plus its two sister properties) was officially underway.

Three Waters Resort and La Siesta Resort. Photos: Keven Gungor

Three Waters Resort is located on Islamorada, one of the 800 keys famous to the southern tip of Florida. Keys are made of coral and are typically much smaller than islands, making them known more for pristine waters and less for sandy beaches. While the spring break crowd is likelier to hit up the beaches of Miami or Fort Lauderdale, the Florida Keys like Islamorada attract a quieter crowd interested in boating, fishing, and stunning oceanside views.

The resort is named after the three surrounding bodies of water: the Atlantic Ocean, the Gulf of Mexico, and the Florida Bay, which all envelop the string of Florida Keys. Hotel guests not only have access to the property’s amenities but also those of the two sister resorts farther down on Islamorada: La Siesta Resort and Amara Cay Resort, accessible both by car and by boat.

The properties share a water taxi cheekily named the “Rum Runner” after the Prohibition-era smuggling of Caribbean liquor. Weather permitting, the Rum Runner operates daily, providing complimentary rides to guests who want to hop on and hang out at the sister properties. Many returning guests ride the water taxi to bar-hop between the three resorts, avoiding concerns about getting behind the wheel of a car or needing to Uber from one spot to the next.

Amara Cay Resort. Photo: Islamorada Resort Collection

Curiosity got the best of me, and I decided to take the Rum Runner to check out the other two resorts. While Three Waters has some of the only human-made sandy beaches in the Keys, La Siesta sports a quieter, more intimate feel featuring cozy cottages and homey amenities like kitchenettes for visitors seeking a staycation away from home. Amara Cay Resort has the largest pool of the three resorts, perfect for guests who want to sunbathe with a beverage in hand. Hopping from one to the next via water taxi took about 20-30 minutes each time.

Photo: Islamorada Resort Collection

Three Waters Resort has four distinct room styles: The Cove, The Ocean, The Resort, and The Cottages. The Cove rooms are part of an adults-only section of the resort that’s separated by a thin body of water that promises seclusion. The Ocean rooms provide beach views while The Resort rooms face lush tropical trees. Finally, The Cottages offer outdoor patios and more spacious accommodations. All rooms cost about $400-600 per night.

I stayed in an Ocean room. Being able to gaze out over the turquoise paradise before me was easily the best part of my room — there’s nothing like waking up to a latte and a fresh breakfast, perched on a balcony and taking in the ocean view.

One of my favorite things about the property was a much subtler detail: the room keys. At this resort, there’s no need to worry about misplacing your key or accidentally leaving it back in your room; this one is wrapped around your arm wristband-style. But unlike typical resort wristbands — which are sticky, constrictive, and uncomfortable — this one is stretchable and removable, so you can take it off before hopping in the water. It’s small details like this that remind you you’re at a top-notch resort.

Photos: Islamorada Resort Collection

What’s fantastic about Three Waters Resort is that it’s one of those properties where you don’t have to leave the resort at all during your stay if you don’t want to. Culinary options end up playing a big role in this. At every corner, there’s a spot to eat.

In addition to a classic tiki bar (aptly named Tiki Bar), the property has two restaurants: Mercado Morada and Little Limón. Mercado Morada celebrates Central American food (think tacos, quesadillas, and tostones) while Little Limón, located right above the former, is all about raw seafood (the spot for oyster, shrimp, and ceviche lovers). A food truck sits at the edge of these eateries for those seeking a quick bite on the go.

On the other side of the property is Islamorada Pizza Co. where you can grab casual slices, as well as Starbucks if you’re craving a caffeine boost after a day in the sun. Lucky Twist has sweet tooths covered, with vegan-free and dairy-free soft serve including the classic local flavor of key lime. Kindler (slated to open later this year) is the final dining option, offering wood-fired fare.

Photo: Islamorada Resort Collection

The great luxury of an oceanside resort is, of course, access to aquatic activities. Other than the obvious — the beach bars and pool lounging — Three Waters facilitates tons of options for those exploring the aqua blue waves.

To start, the resort has more than 100 slips if you have your own boat. Otherwise, you can book a Tiki Bar Boat ($1,600-2,000) for private group excursions to the Islamorada Sandbar, a shallow spot in the ocean less than a mile from the shore. Guests wanting more thrill can book a jet ski tour for 90 minutes ($199) or pedal away on a two-person CatBoat tour for two hours ($299).

For those who prefer to appreciate the water from a distance, on-land activities at the resort include grabbing bait at the marina and feeding tarpon from above on the dock or renting a poolside cabana, which comes with a $250 food and drink credit. Golfers can practice their swings facing the ocean — for $125, you can get 50 Albus Golf EcoBioBalls, which are 100 percent safe, biodegradable, non-toxic, and filled with fish food. Elsewhere, the now-open Angler’s Arcade also provides an air-conditioned venue where kids and adults alike can play nostalgic video games and try their luck at carnival-esque claw machines.

You get the idea — the list of activities and amenities at Three Waters is long. But if my arrival is anything to go by, some of the most memorable experiences the hotel can arrange for guests are the Miami Seaplane Tours. From private charters to island escapes, this is an excellent way to see even more of the Florida Keys.

Islamorada is a 1.5- to two-hour road trip from Miami. Though Key West has its own airport, it’s about two hours from Islamorada by car, so either way, guests visiting Three Waters Resort must take a scenic route to get to the property.

Of course, there’s always the option to get there via seaplane from Miami, which cuts the time in half at about a 45-minute flight.

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