Parasailing is as close as you can get to Flying like an Eagle! Caribbean Watersports offers the most spectacular Sky-Soaring flights available in the Keys.

We are the most experienced and most trusted Certified USCG Licensed parasail operator, flying for over 33 years. Our Captains, Crew, and Vessel meets and exceeds all current USCG Safety Standards and FAA regulations for Tour and Parasailing Craft and meets the New 2014 STATE OF FLORIDA PARASAIL STATUTE. We hold a current USCG UVP Seal of Safety, one of the few in the Keys!

Solo Flyer $80; Tandem Flyers $145; Triple Flyers $220; Repeats (on same trip) $35; Riders (if space) $25;

Time listed includes entire experience, not just airtime. Times may vary depending on passengers, weather, and other conditions.

Check out some pages and listings you may be interested in:

21ft Proline 150HP

19ft Aquasport 115HP

PaddleBoard Rentals (SUP)s- 4hrs

18′ Wagner Poling Skiffs

Hand Gliding Tandem

23′ Pontoon Boat – Sunchaser

Kayak Rental (up to 3 person)

20′ Pontoon Boat – Sylvan

20′ Pontoon – Sylvan

Genevieve Roberts

Captain Lolly and first mate Ray were excellent host for our sunset sail. We had a hard time calling or using the website to make a reservation so we did it the old fashioned way and just went there in person. The trip was awesome because of the smaller catamaran, fun feel, relaxed atmosphere overand champagne toast at sunset. I recommend bringing additional drinks and appetizers.

Bill Clarke

We did the Sunset Sail aboard Carolina Moon, with Capt. Lolly during a recent family vacation. She's a great captain, very knowledgeable and made sure everyone had a great time. The sunset over Florida Bay and Key Largo with a champagne toast didn't disappoint either. I have some sailing experience so she even let me take the helm for a few minutes while her and the First Mate were taking some photos. Highly recommend this, we were guests at Playa Largo Resort but I'm not sure if that's a requirement or if they offer this to non-hotel guests as well.

Tim Genua

Capt Lolly and Ray took us on a great sailing and snorkeling adventure.nCapt. Lolly was very knowledgeable and explained many details about the area and the undersea life.nOur entire group had an awesome time! Highly recommend this trip.

Gavekshika Dissanayake

Had the best time yesterday on the sunset cruise. We took our baby for the first time and he had a great time too! Nice music. Champagne and sunset. Capt. Lolly and Ray made sure weu2019re having fun! Canu2019t wait to do this again next time weu2019re here!

Seamus McEntee

My kids and I parasailed today for our first time. Seth and Marissa were awesome! Marissa took great photos and videos, so my wife who watched onboard could truly enjoy the experience. Definitely the highlight of our trip to Key Largo!

Caribbean Watersports Parasailing Key Largo

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