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Captain Jason Beasley


CAPTAIN JASON BEASLEY is the founder of Cloud 9 Sailing Adventures.


He discovered sailing in high school when a friend bought a hobby cat and they learned to sail by trial and error, flipping the boat every way possible. His friends dubbed him a "sailing fanatic" and knew his dream was that some day he would own a sail boat and take people sailing for a living. Years went on, he bought his first monohull sailboat (these don't flip!), then his second and third. He spent most weekends sailing on the lakes of Texas, learning to art of sailboat racing and honing his skills as an avid sailor.


In 2004 he purchased the original Cloud 9 sailboat in Texas, a 40' Beneteau designed for the Caribbean, and named it "Living on Cloud 9". Which is what he planned to do! It took a year of planning his adventure and future business. He had to sell his home and most of his possessions, just taking what was most important with him, along with his two kitty cats.

Off he sailed! across the Atlantic Ocean to the Caribbean Sea. What an adventure for a man and his two cats, luckily two friends joined him in Florida for the rest of the journey. Nine days across the Atlantic with 25, 30 and 35 knot winds / 15', 30' and even 60' seas. Not much sleep, not much food, and the beer went untouched until arriving in the US Virgin Islands. What a dream arriving to calm turquoise seas, a calm anchorage to finally sleep, and Ice Cream!


Jason spent his first year sailing all the Virgin Islands, getting to know the area. He easily determined that St John was the best place to be and started offering day sail and snorkel trips. Over the years the business grew, a second 47' Beneteau was added to the Fleet and Cloud 9 became a well known popular day sail charter business.

We have made many wonderful friends over the years, and shared many great experiences. Take a trip on Cloud 9 and let Captain Jason entertain you with all his stories.


Captain Jason has his 100 ton master captain license, plus all the safety equipment required! The boats are licensed, insured and Coast Guard approved.


Jason loves sailing and is always willing to share his knowledge or even let you take a turn at the helm. Whether it is your first time on a sailboat or you are an experienced sailor he will make sure you have a good time and experience sailing at it’s best! 

Our Additional Captains & Crew


We only hire the best! 

All of our licensed captains have extensive sailing experience and charter boat experience...  

All of our Captains and crew are safety trained, CPR and first-aid certified.


You can be assured that all of our Cloud 9 Captains know the Cloud 9 routine and our crew will provide you with personalized customer service . We always try to pair a team that will share thier knowledge of both sailing and the underwater world.


Our captains will entertain you with stories throughout the day. Our crew will spoil you with drinks and service. If you need snorkeling instruction or would like a guided tour, we are always willing to get in the water with you.  Our crew is great at finding and identifying all the local fish and critters.

We have been blessed to have this young girl Marliegh join Megan Eberwine as a "junior crew in training" on many Cloud 9 Sailing trips.

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