Begin your adventure on land with exclusive access to a limited access beach — a hidden gem that feels worlds away from crowded public shores. With your included day pass, you’ll have access to optional beach amenities such as shaded umbrellas, picnic tables, and BBQ grills — all available at very reasonable rates if you’d like to add them to your day. Whether you’re laying out with a book, dipping your toes in the water, or simply soaking in the laid-back island atmosphere, this is the perfect way to ease into your Keys experience before heading out on the water.

As the afternoon softens into golden hour, step aboard your own mini pontoon boat for a guided sunset cruise. After a full safety and operating briefing, you’ll drive your own boat, following our lead boat along a relaxed 6.5-mile route through the calm, protected waters of Blackwater Sound.

Cruise along the shoreline, passing stunning waterfront homes and elegant island estates — each one telling its own story of life in the Keys. The pace is slow, the water is smooth, and the breeze is just enough to remind you that you’ve officially left the stress of everyday life behind. This part of the journey is all about soaking it in: the colors of the sky, the sparkle of the water, and the peaceful rhythm of the sound.

Next, the route crosses Lake Surprise, a wide, peaceful stretch of water with a surprising past. Early surveyors mapping Henry Flagler’s Overseas Railroad in 1902 didn’t even know the lake existed until they suddenly came upon it. Constructing the railroad here took over a year of dredging through thick peat to create a solid foundation.

From there, glide into the iconic Jewfish Creek passage, a narrow and picturesque waterway that connects Blackwater Sound to Florida Bay. It’s a favorite stretch among locals and visitors alike, offering a unique perspective of the Keys from the water. Keep an eye out for seabirds, manatees, and the occasional dolphin — nature has a way of making surprise appearances when you least expect it.

As the cruise continues, pass the lively shoreline of Gilbert’s Resort, where music often drifts across the water and the energy of island life comes alive. It’s the perfect contrast to the serenity of the sound — a reminder that the Keys can be both peaceful and vibrant, sometimes in the very same moment. Just across the water from Gilbert’s sits Houseboat Row, a colorful line of floating homes that feel like their own tiny waterfront neighborhood. Each one has its own personality, offering a glimpse into one of the Keys’ most unique ways of living on the water.

And then comes the highlight of it all: the sunset. Timing is everything, and your return route is carefully planned so you arrive back near the dock just as the sun dips low on the horizon. The sky transforms into a canvas of fiery oranges, soft pinks, and deep purples, reflecting off the calm water in a way that simply can’t be captured in photos.