The Weiss Family

Captains's - Kristie & Richard


Kristie & Rich met in flight school in the early 90's. After receiving their commercial licenses and flight instructors certification they moved to Central PA, where they started their own Flight School and taught over 200 people how to fly.

Rich grew up in Ft. Lauderdale and was always around boats. Kristie and Rich started vacationing in The Virgin Islands in 2000, when they rented a power bareboat for a week-long charter. They were immediately hooked on boating and island hopping!

In 2013, they bought "Sail Pending" and have sailed the entire Caribbean Sea from Trinidad to Mexico, but never found another area that felt more like home than the Virgin Islands.

They moved to The Virgin Islands in 2017 and purchased, the two iconic day charter boats; Pirates Penny and Stormy Petrel and started Stormy Pirates Boat Charters.

Their son, Tyler grew up sailing and boating. He is actively involved with the daily operation of the business and you will see him around the docks and/or on the boats everyday.


Kristie also proudly serves as a member on the Board of Directors of  VIPCA (Virgin Islands Profession Charter Association) which unify's, builds and supports all aspects of the marine industry in the Virgin Islands.



Tyler is Kristie & Rich's only child is the true, "Son of a Son, of a Sailor." His entire life, he has been very hands-on and has enjoyed many activities such as flying, sailing, photography and more.

Before Tyler could even walk, he has been visiting the Virgin Islands and has gained an abundance of local knowledge.

Tyler has sailed over 20,000 nautical miles with his family, has logged over 1000 days at sea and has sailed to over 100 different islands in 16 different countries.

Tyler enjoys sharing his knowledge and experiences of the Virgin Islands along with our guests.

We are a family owned and operated company.

Our Owners & Crew Members are long time Virgin Islands residents and not just seasonal workers or live on the island part time.

We are all here full time and the Virgin Islands is our home.

We are proud of the fact, that as a guest you will get to see the same crew members year after year.

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