Caribbean Watersports
Caribbean Watersports
5
Parasailing & Paragliding • Scuba & Snorkelling • Boat Tours • Eco Tours • Private Tours
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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
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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! Can you see yourself "Raising Hull!" on a Hobie-Cat sailboat!? Or witnessing our breath-taking 25-MILE bird's-eye-view of Florida Bay & Pennekamp Park by Parasail? ...How about encountering wild dolphins on our incredible 2-HR Eco-Tour! Or Morning Mimosa Sip-n-Swim/Sail or Finish the day on a Champagne Sunset Cruise on the 24 passenger 'Carolina Moon' Sailing Catamaran! All Tours are Private or at 1/2 capacity for social distancing. CDC Safety Protocols followed. 97450 O/S Hwy, Sol by the Sea Marina.
Key Largo, Florida
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Awards
Travelers' Choice
2022
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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions
5.0
871 reviews
Excellent
811
Very good
33
Average
8
Poor
8
Terrible
13
Layna
1 contribution
Mar 2023 • Family
Captain Lolly and Ray Ray made our day in Key Largo! We were inexperienced sailors, paddle boarders, and snorkelers with children and they made us all feel comfortable and safe while we still had a fantastic adventure! Give them a call! We were supposed to have a sunset cruise but because of the weather they let us do the snorkel sailing adventure instead. Thank you all!
Written March 19, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Cvb804
2 contributions
Mar 2023 • Friends
My mom and I did a sunset cruise with Lolly and Ray and had a spectacular time! The sunset was incredibly gorgeous and Ray and Lolly did a great job of leading the charge in making sure we experienced all of its beauty. They took incredible photos of us, provided some champagne for a light toast, and honestly were just great company to have and chat with over the course of the evening. I really appreciated all of the effort they put into making for a wonderful evening. Would highly recommend this excursion 😊
Written March 7, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Tykatmom10
12 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.
Nancy W
2 contributions
Dec 2021 • Couples
We (the Winebrenner’s) took the sunset cruise on Dec 6 on the “Carolina Moon”. Captain Lolly was great as well as Stew. Interacted with every one, very informative, played great music. It was a very pleasurable trip. Highly recommend to take this tour with this captain. We plan on doing it again.
Written December 6, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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.
Rachel W
1 contribution
Jun 2022 • Family
Capt Lolly and Jersey Stu made the ride incredible. They were very knowledgeable about the water/wildlife. Made the ride super fun. And were so kind and interactive. 10/10 would recommend taking the sunset cruise or any other activity with them.
Written June 16, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
EFamilyTravelers
Coral Gables, FL30 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.
Tracy W
Palm Bay, FL22 contributions
Jul 2022 • Couples
We did the parasailing and the sunset cruise with Carribean Watersports. Both trips were amazing! Marissa on the parasailing trip was amazing at making us feel comfortable and making sure we had an amazing time. She even took pictures of us while we were up in the air. I would highly recommend this trip!
Captain Lolly and Stu were also amazing on the sunset cruise. They took pictures of us throughout our trip and at sunset. The boat was clean and well maintained. We felt safe and had a wonderful time. I would highly recommend this cruise!
Captain Lolly and Stu were also amazing on the sunset cruise. They took pictures of us throughout our trip and at sunset. The boat was clean and well maintained. We felt safe and had a wonderful time. I would highly recommend this cruise!
Written July 25, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
TomWilkeIllinois
Collinsville, IL13 contributions
Feb 2022 • Couples
We've been looking for a nice place to sail on a Hobie cat, and we found it here . The great customer service started when I called to a busy signal, but immediately got a nice return text along with the answer to my question. The rate was about $125 for a two hour ride and checkin was very easy. We got to the hotel before the lot filled up ànd had only a short walk to the beach ramp. The dock hand was very helpful and the boat a 13ft, was in great condition. We had a nice sail around Florida Bay, very relaxing. A great experience for sure!
Written February 26, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Lemiah7
Homestead, FL2 contributions
Jun 2022 • Couples
This was the most amazing Sunset trip on the Carolina Moon Catamaran in Key Largo, FL. Thankful to God to Celebrate my 50th birthday with my Family. We were welcome by Victoria and Chase at the Caribbean Watersports desk underneath the Sol by the Sea restaurant. Both of them are very kind and welcoming with smiles. Captain Lolly is the BEST and Jersey Stu is an amazing mate they both made sure that it’s safety first. It was off course the best weather for the Sunset Cruise, prayer helps 😉. You are able to connect your play list to their Bluetooth so come prepared with your best playlist. And be ready to “STRIKE A POSE”, Captain Lolly is there to make sure the special moments are capture, this was such an unexpected treat. We received a luscious cheese platter and a delicious bowl of fruit. Thanks to Chef Gaby from Playa Largo Resort & Spa Kitchen. Through out the trip we were very well taken care of and Captain Lolly with so much experience made us all feel safe and secure as we chased the Sun setting, with both sails up and no motor running just allowing the natural breeze to move us all along was such a beautiful experience. Jersey Stu assisted us through the trip. The Champagne Toast was the cherry on top right at the Sunset. Thank you very much to all the fantastic team at Caribean Watersports you made this sunset cruise one of the highlights of my 50th Celebration.
Written June 19, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Sohail M
Doha, Qatar89 contributions
Covid question...do the staff at this company wear masks?
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.
Majse74
Naestved, Denmark238 contributions
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?
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!
Bebe L
8 contributions
Do you do snorkeling trips? And do you rent the equipment?
Cws_Gurl1
Key Largo, FL17 contributions
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
Ondine C
Boynton Beach, FL77 contributions
How long is your parasail ride? I saw on another company’s website that it’s only 8-10 minutes. Why so short?
Concierge C
Key Largo, FL3 contributions
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.
Is there an open beach for a one year old to hang out?
KeysDazza
Key Largo, FL30 contributions
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
Bristol, UK1 contribution
How much is paddle board rental?
Concierge C
Key Largo, FL3 contributions
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
Sorrels13
Alpharetta, GA111 contributions
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.
Concierge C
Key Largo, FL3 contributions
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!