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Caribbean Watersports

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Open Now: 9:00 AM - 5:00 PM
Open today: 9:00 AM - 5:00 PM

Caribbean Watersports
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Certificate of Excellence
Traveler Overview
  • Excellent92%
  • Very good5%
  • Average1%
  • Poor1%
  • Terrible1%
Travelers talk about
“captain dan”(70 reviews)
“enviro tour”(42 reviews)
“jet ski”(30 reviews)
The CARIBBEAN WATERSPORTS family would like to extend our warmest welcome! ...Whether you are staying in the Keys, or just driving through, we want our guests to experience our unique Islands, our exceptional climate, and just truly learn how to...more
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Hours Today: 9:00 AM - 5:00 PM
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Suggested duration: More than 3 hours
97000 Overseas Hwy, Playa Largo Resort & Spa, Autograph Collection by Marriott Worldwide, Key Largo, FL 33037-2210
+1 305-619-7844
Reviews (456)
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All reviews captain dan enviro tour jet ski hilton hotel florida bay parasailing trip mangrove islands sunset cruise everglades national park two hours paddle boarding private tour fish hour tour highlight of our trip the florida keys these guys
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1 - 10 of 448 reviews
Reviewed today via mobile

I went parasailing with Captain Jordan and Captain Nick yesterday. It was amazing.. having been afraid of heights for years, this was a big leap for me. Nick explained everything that was going to happen and I was completely prepared.. Jordan made sure that my...More

Thank marthaschap
Reviewed 3 days ago via mobile

Highly recommend !! Five star service & equipment. We rented SUP boards, kayaks and the sunset sailing cruise was the highlight of our trip. TOP NOTCH!!!

1  Thank Janet H
Reviewed 4 days ago via mobile

The team at Caribbean Watersports made sure we had a memorable experience aboard the Carolina Moon catamaran. They will answer all of your questions to put you at ease and will go the extra mile to make sure you have the best experience possible. Capt....More

1  Thank Happiness619210
Reviewed 1 week ago

Highly recommended! Caribbean Watersports was able to fit us in on short notice when our original seaside tour cancelled due to rough seas. Bayside was calmer seas, so off we went! Captain Lolly and her team were great! The Catamaran was clean and gear was...More

1  Thank Rose M
Reviewed 1 week ago via mobile

Capt Jordan, Capt Nick and Victoria are the best at their job. Treated us like royalty and provided a great experience. Parasailing is a must when in the keys and these people do it right!! Safe, gorgeousviewd and just the right amount of airtime. Go...More

Thank Trip219941
Reviewed 1 week ago

Highly recommend! The team at Caribbean Watersports is so kind and personable! We went on a sunset sail during Labor Day weekend - It was supposed to be on the Carolina Moon, but the winds weren't going to be good for the catamaran. Everyone who...More

Thank Ashley B
Reviewed 1 week ago via mobile

we time went out with coats Lolly and Ginny. Stopped and jumped overboard and saw starfish, sea urchins, and kids loved cruising on the catamaran. Great hospitality. funny, kind, and adventurous! we would do it again for sure!

1  Thank MattEth
Reviewed 2 weeks ago

Just returned home from a great trip to Key Largo... I highly recommend Caribbean Watersports to anyone visiting the Keys! Our family rented a Hobie to sail and a standup paddle board while we were staying at Playa Largo. Victoria & Jordan were awesome! Our...More

2  Thank Erin A
Reviewed 2 weeks ago

We did an enviro tour boat trip, and it was fantastic. Our guide Nick was really knowledgeable and fun. He made sure we saw tons of mangroves and pointed out a variety of birds. Finding a manatee in one of the canals was one of...More

1  Thank Pandora402
Reviewed 3 weeks ago

Our sunset cruise on the Carolina Moon was excellent. Captain Lolly Carpenter made the trip fun for my friends and I. We sipped champagne at sunset and she let me blow the conch shell. An added bonus, she took great pictures of us and sent...More

2  Thank Traveler221640
Concierge C, Guest Relations Manager at Caribbean Watersports, responded to this reviewResponded 3 weeks ago

Thank you for the kind review! Our team here at Playa Largo Watersports really go the extra distance to make our home, your home. Victoria and Captain Lolly were thrilled to see your review and thank you for sharing any photo's.

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Questions & Answers
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Ondine C
September 17, 2018|
Response from Concierge C | Property representative |
We have a max of 6 passengers on our 30’ Parasail vessel and many times we fly tandems (2 flyers at same time) over an average of 1 hour. Most of our actual flight times are 10-12 mins air time. Repeats are only $30 if you... More
Viviana A
March 8, 2018|
AnswerShow all 4 answers
Response from KeysDazza | Property representative |
Both of our two locations have a shallow sandy swimming beach. We even have a unique 7’ Island Float with an anchor for kids and adults to enjoy the water.
Sally L
June 25, 2017|
Response from Concierge C | Property representative |
Our Paddleboards are the Yolo Yak, a board with four points underneath for maximum stability. We also have the ASAP boards at our other location 1/2 mile north on the bay and the new Hobie Eclipse. Places start at $40 for... More