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 children, Captian Kaycie and Tyler grew up sailing and boating. They are both very involved with the daily operation of the business and you will see them around the docks and/or on the boats everyday.

Captain Kaycie


As Kristie & Richard's daughter Kaycie spent the first few years of her life as an airport kid, riding in the back of airplanes while her parents gave lessons to students.

Her need for adventure continued as she grew older. After living in Manhattan, the British Virgin Islands and extensive travel through 20+ countries, her anchor has set in the US Virgin Islands.

Kaycie loves being on the water and has worked hard over the years to obtain her Coast Guard Master License. She loves keeping guests entertained with Virgin Islands history and pirate tales.



Tyler 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 on vacation and has gained an abundance of local knowledge. Tyler has sailed over 20,000 nautical miles with his family, has 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.

Kaycie & Tyler sailing in St. Maartin 2009
Kaycie & Tyler sailing in St. Maartin 2009
The Grenadines 2015
The Grenadines 2015
Tyler always loved to drive.
Tyler always loved to drive.

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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