Caribbean Watersports
Caribbean Watersports
5
Scuba & SnorkellingWater SportsEco ToursNature & Wildlife ToursKayaking & Canoeing
9:00 AM - 6:00 PM
Monday
9:00 AM - 6:00 PM
Tuesday
9:00 AM - 6:00 PM
Wednesday
9:00 AM - 6:00 PM
Thursday
9:00 AM - 6:00 PM
Friday
9:00 AM - 6:00 PM
Saturday
9:00 AM - 6:00 PM
Sunday
9:00 AM - 6:00 PM
Full view
About
The CARIBBEAN WATERSPORTS located at Playa Largo Resort (97450 Overseas Hwy, Key Largo) 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 kick back, relax, and get "wild, wet, spilled & thrilled!" in the beautiful Florida sunshine. ...Take this tropical paradise and combine it with our 35-years of experience, and will you have the makings of a TRULY remarkable vacation!
Key Largo, United States
Meets animal welfare guidelines
Awards
Travelers' Choice
2024
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
5.0
935 reviews
Excellent
873
Very good
33
Average
8
Poor
8
Terrible
13
Mcgdonna@aol.com
1 contribution
Jun 2020
We chartered a private sunset cruise with Captain Lolly and Ginny on June 16 for a birthday celebration. "Oh, what a night" for a sunset cruise!! Not only was the weather perfect and the sunset amazing, the sail and crew were outstanding!! We had drinks and a special fruit and cheese tray which made the celebration even better. Captain Lolly and Ginny were so friendly and we talked to them like they were part of our family. I highly recommend Caribbean Watersports and the Carolina Moon for a sunset cruise while you vacation in Key Largo
Written June 24, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
MarileeFree
Key Largo, FL45 contributions
Jan 2020 • Solo
Fantastic sunset sail with Captain Lolly and Captain Ginny, these gals made sailing on a windy day look effortless on the 38 foot Carolina Moon Catamaran. Such a treat to see the sunset and the sights of the Florida Bay with all the kind, fun folks on board. Special thanks for all the great pictures to capture the memories, it’s truly amazing out there! Can’t thank you enough for the laughs, music, fun and new friends. I highly recommend this tour, Captain Lolly, you filled my heart with the joy and magic of sailing, like no other Captain I know. Can’t wait to do it again!✌️❤️⛵️
Written January 9, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Peyton F
2 contributions
Feb 2020 • Couples
We had an amazing time on the water with Captain Lolly and Hannah! We called the morning of and Caribbean Watersports was very accommodating. They gave us options and even though it was windy, explained that the bay side would be safe to sail. Captain Lolly and Hannah knew their stuff, shared fun facts about the wildlife and islands, and made the experience great! They made us mimosas and we got to go snorkeling and stand up paddle boarding. We saw starfish, jellyfish and even a dolphin! We would recommend anyone looking for a fun afternoon to call them up and request the amazing all girl crew!
Written February 9, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
EFamilyTravelers
Coral Gables, FL41 contributions
Sep 2020 • Couples
We came for the long weekend and decided to do a sunset cruise. Caribbean Watersports is conveniently located on the Playa Largo Hotel premises under El Sol Restaurant and Yami was very informative with cruise details. We were a bit concerned since it had rained earlier in the afternoon, however Victoria assured us that she had verified that the weather would be good. It was wonderful. We took a ride with Captain Lolly and Captain Jenny on the Carolina Moon just before sunset. They took us to a great spot with snorkeling, clear waters and beautiful mangroves. It was to tranquil and beautiful. The sunset cruise came with Champagne, fruits, Croissants and delicious cookies from a local bakery. My husband and I enjoyed conversation with the captains. Captain Lolly is also a great photographer and even took drone photos!!! Having someone else taking photos was really special so I could enjoy the moment but yet have the photos memories as well. Highly recommended.
Written September 6, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Joyce D
3 contributions
Jan 2020
We had an amazing sail on the Carolina Moon with Captain Lolly and Ginny. These women created a perfect late afternoon experience for our family and friends as we held a memorial service for my Dad. "Paw" (as everyone called him) loved sailing on Florida Bay. We shared memories, music and food. Many thanks to these wonderful women for thinking of everything and supporting us on this journey.
Smooth sailing to all!
Smooth sailing to all!
Written January 13, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
TobyandElmer
4 contributions
Dec 2019 • Couples
Captain Lolly and the whole crew are awesome. It was an especially eventful sunset sail, net with wonderful skill, talent and entertainment. Plus the vibe was just great with everyone. And our dogs were treated wonderfully as well. At one point a plastic bag accidentally flu overboard and everyone on the ship pull together to turn back and collect the bag. Well done captain and crew and passengers!
Written January 1, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
WesD
Coral Springs, FL18 contributions
Jun 2020
It’s a bit pricey, but they’re located at the Playa Largo Resort, have new Yamaha wave runners that can go 79 mph (I checked), the guided tour in the Florida Bay traverses mostly calm waters, and they take a video and photo of your party during the tour, PLUS AirDrop it right onto your phone back on shore for free! We skipped the parasailing but it looked fun and you are able to see over Key Largo to the ocean. We did the snorkeling which was at a mangrove island aboard a catamaran, but I’d recommend this tour for young kids or beginners and personally snorkel the coral reef. Pictures were also texted to us after snorkeling by our wonderful captains.
Written June 20, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Josh F
San Ramon, CA18 contributions
Jul 2020 • Family
Definitely one of, if not the highlight of our vacation was the Sunset Cruise on the Carolina Moon catamaran. Our captain Lolly and crew Hannah were absolutely awesome. They gave us a really great safety briefing which was important (we had a family of six, ages 2-75) then we set off on a 3 hour sail. Lolly was fantastic. Her photography skills are awesome and she ended up taking about 50 photos of us with her own phone and sending them to us. We took a stop for a few of us to snorkel at Pelican island. My wife paddle boarded for the 1st time with some good guidance from Hannah.
We took in a fantastic sunset and then returned to the dock.
The boat was a perfect set-up and size with covered seating and the two trampolines under the sails.
We brought our own food and drinks which they stored in their cooler, But were also provided with cheese and champagne.
Overall- a 5* trip.
Relaxing, great crew, safe and a stunning sunset. Highly recommend.
We took in a fantastic sunset and then returned to the dock.
The boat was a perfect set-up and size with covered seating and the two trampolines under the sails.
We brought our own food and drinks which they stored in their cooler, But were also provided with cheese and champagne.
Overall- a 5* trip.
Relaxing, great crew, safe and a stunning sunset. Highly recommend.
Written July 27, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Faith L
Lake Mary, FL169 contributions
Jul 2020 • Family
My family of 4 went on the best parasail experience with Caribbean Watersports! I was nervous to go up with my 13 year old, but the captain put us totally at ease with his expertise and calm guidance. He had my husband take a slow-mo video of the sail opening, what a helpful idea! It was a flawless adventure and a great bonding experience for our family. He’s been safely treating guests to water sports for over 30 years, and it shows!
Written July 12, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Tykatmom10
16 contributions
Dec 2021 • Family
We had the best time on our sunset sail. Lolly and Stu really made the trip special. We were meeting our son’s girlfriend’s family for the first time. We had a lovely cheese tray and champagne. Lolly had some great ideas for pictures with our group and Stu was sure that everyone was comfortable and having fun. We could not have asked for a better first time meeting experience - the warm weather, Christmas music playlist, beautiful sunset, and attentive crew was priceless. The catamaran is perfect for experienced sailors as well as first timers. I highly recommend this experience when visiting Key Largo. Carribean Watersports is a professional company who knows how to provide great service and a lot of fun.
Written December 30, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Covid question...do the staff at this company wear masks?
Written April 13, 2021
While on Property and under cover, our staff wear masks and on our vessels as required by the USCG currently. Most have completed their Covid vaccinations. All equipment are sanitized after each use.
Written April 27, 2021
Which public tours do You offer (in early May)?
I´m interested in Your Enviro Tour and the 04:30 PM Caribbean Cruiser 3 hr Snorkel with Sunset.
Can they all be done as a part of a public tour?
Written November 17, 2019
Our Enviro-Tour is 2 hours w/2-6 guests. Departure times 9;05 & 11:30 am and 3:30 pm
Our Caribbean Cruiser is private chartered for up to 6 guests for Coral Reef snorkeling or Island/Beach tours. 3 hours allows seeing the bay and ocean and over an hour on site at many reefs. Add extra time to see more reefs, Alligator Reef Lighthouse, Islamorada Sand Bar and more! We can adjust to sunset time on way back in for better view if sunset, too! Charter prices can be split between different parties.
Our 24 passenger Carolina Moon Sailing Catamaran offers both public and Private Adventure and Champagne Sunset 🌅 Cruises on shallow Florida Bay, too.
Many of our options are rated 5 Stars on over 554 TripAdvisor reviews.
Contact us via our website email. Thank you!
Written November 17, 2019
Do you do snorkeling trips? And do you rent the equipment?
Written November 4, 2018
Thank you for your inquiry! We have many different types of snorkeling trips, public and private Oceanside reef trips, as well as public or private bayside island snorkels! We also have mask and snorkel gear to rent right from our beach at Playa Largo Resort! For pricing please contact us directly (text messages preferred) at 305-619-7844 or 305-852-4707!
Fair winds & Sunny skies,
CWS Desk Manager
Written November 4, 2018
How long is your parasail ride? I saw on another company’s website that it’s only 8-10 minutes. Why so short?
Written September 17, 2018
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 want to change parters. Bring up a phone and video or Facetime! We meet all USCG and State of Florida rules for Parasailing.
Written September 18, 2018
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.
Written March 11, 2018
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 the first hour, $15 each after.
Check out our website for more information or call us direct at 305-852-4707
Written July 11, 2017
For people who have done jet skis before, what sort of area are you allowed to go to? Is it a fairly small area close to the beach or do they let you venture out some? I understand there will be some limitations but just curious how restricted it is.
Thank you.
Written May 1, 2015
Thank you for asking. We need to be able to respond to an emergency as soon as we see anyone in difficulty. Our ride area is almost a mile square and in sight of our beach hut.
We only run 5 skis so it's not too crowded and less likely to have a collision.
It's fun and pretty safe for all to enjoy on our shallow 6' bay. No canals to idle
through to the ride area, just 100 yards from shore then full speed ahead!
Written May 1, 2015
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