Captain Charlie Whittemore

Captain Charlie is originally from California and has been sailing since the age of five. He learned to sail in San Francisco and later moved to Laguna Beach in Southern California where he continued to sail. Charlie moved east to Rhode Island where he attended and graduated from the University of Rhode Island with a Bachelor's Degree in Sociology and a minor in Cultural Anthropology. Post college, Charlie relocated back to Laguna and worked in the hospitality industry and has covered the full spectrum from cooking to hotel management. He later opened his own merchandising and marketing business for the action sport retail market. Looking for a change, Charlie moved to St. Thomas in 2001 where he received his U.S. Coast Guard Captains License. Charlie never looked back and started Simplicity Charters in 2006. He called on his best friend from college and expert sailor Josh Rutty to come and join him as co-captain and first mate. Charlie is certainly enjoying the ride and looks forward to expanding his fleet in the next few years.

Josh Rutty (1st mate / co-captain)

Josh Rutty grew up sailing the waters of the Connecticut River where he gained an appreciation for the sea that he never lost. At age 12, Josh started racing in Junior regattas up and down the East Coast. By 15, he was teaching sailing and racing at numerous yacht clubs in Connecticut. Josh attended the University of Rhode Island and graduated with a Bachelors Degree in Marine Affairs. Studies included Marine Biology, Oceanography as well as Marine Coastal Law. Josh moved to California and worked in the green movement, dealing with waste water management problems of San Diego. Finding out environmental crusading is not that lucrative. Josh spent his time as head chef for the Mission Bay Country Club and later managed timeshare apartments in Pacific Beach, CA. 2006 Josh received "The Call"; Move to St. Thomas to start a charter business with long time friend Charlie? Josh is now a Licensed USCG Captain and is enjoying learning from all the natural wonders of the Islands.

Hinckley was a coconut terrier that we rescued here in St. Thomas when she was only ten weeks old. She was a jack russell terrier, beagle, and whippet mix. Hinckley lived aboard with the family and was a true salt sailing the seas with us for eleven years.
The time has come to celebrate the life of our best friend, Admiral Hinckley, the smiling sailor dog. She brought joy to our family, friends, and most of all, the guests who keep returning to be a part of Simplicity Charters. Thanks girl. We will always love you and cherish all of the memories we shared together.