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Sunset cruises are among the most popular activities in the Florida Keys, allowing visitors to enjoy the fabulous colors and calmness of the sunset from the water. Viewing the evening from the waters surrounding the Florida Keys is a unique and charming experience, with an astounding array of pink, purple, and orange hues tinting the sky and reflecting off the tranquil waters of the Florida Bay and Gulf of Mexico.

“…a unique and charming experience…”

There are several things to consider before planning a sunset cruise, such as whether you would prefer to rent a boat or hire a licensed Captain. If you’re unfamiliar with the area, having a captain doubling as a guide with their local knowledge can be extremely helpful. In addition, you’ll be able to more thoroughly enjoy your time relaxing on a gentle cruise without worrying about where to go, what to bring, any prerequisites, etc.

There are many options when selecting a charter for a sunset cruise. Typically, these charters last about two hours and take place aboard a sailboat or catamaran, some offering additional amenities, such as drinks and dinner.

Calypso Sailing & Pirate Choice

(305) 896-8004
Mile Marker 100 Oceanside
99701 Overseas Hwy, Key Largo, FL 33037
Enjoy a unique charter experience aboard one of several luxury catamarans such as the “Lady Susan” equipped with a variety of water sports equipment to make the most of your aquatic excursion. Whether relaxing or hands-on sailing, the “Bloody Pirate” offers an authentic setting to visit local tropical reefs.


You might think that sunset cruises are solely intended for romantic outings, but many of these charters are also equipped to host families and friends! So, whether you’re a couple seeking romance, a family with young children, or friends searching for an exciting and new experience, you can look forward to a charter designed to cater to your group’s needs!

If you’re planning your itinerary to the fabulous Florida Keys, you’ll want to set aside time for a sunset cruise. They’re suitable for all those who want to experience the beauty of the Florida Keys from the water and are a surefire way to create lasting memories. Relax and unwind as you take in the majesty of the sunset during a cruise in the Florida Keys!

Activities Guide —

If you want more recommendations on what to do and where to eat, we highly suggest you visit our Activities Guide. There’s heaps of information neatly organized by type of activity and location, so you can quickly find what you’re looking for with only quality suggestions listed.

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