fiji-1385-2Owner Kimber Tracy was born & raised on Oahu, Hawaii. The daughter of passionate lifelong sailors, her birth announcement was written as a ship launch, providing her length on the waterline, beam & gross tonnage. With an intense love of the ocean, Kimber was an avid surfer, got into scuba diving early on, sailed every weekend & worked at the Waikiki Aquarium in Dolphin & Monk Seal volunteer research programs for many years. Her first study expedition was to ID Humpback whales in Alaska aboard a 65 ft. Ketch sailing the magnificent inside passage in 1981. A passion was born, and she has since sailed aboard virtually every type of vessel imaginable, from traditional Dhows off the coast of Kenya & down the Nile, to the Swedish tall ship Tre Kronor over the Baltic. A lifelong love of adventure & exploration has driven her to the four corners of the world, having thus far traveled to over 50 countries, mostly solo. She enjoyed a career as a successful entrepreneur & corporate executive both in the US and Europe. A stint as a business consultant for a well established Charter company ignited an interest to enter the sailing industry as a second career, and after searching for the perfect place to start the company, she settled on lovely little Key West. Kimber enjoys the opportunity to combine her endearing love of the ocean, passion for adventure, international experience of five star hospitality and several years co-owning a gourmet catering company, with a genuine enthusiasm for helping people fulfill their dream of “sailing off into the sunset” in one of the most beautiful sailing grounds in the United States. Her attention to detail and desire to ensure her clients have a first class time aboard is readily apparent from beginning to end of every Course or Charter. She is joined by a team of consummate maritime professionals & land based staff, who together endeavor to deliver a truly fine experience to their clients.  

Captain Jon Skiffington, following his family heritage, came into sailing as a bucket list “must do”. He learned everything he could about sailing, boats, boat systems & maintenance and managed to cram a good deal of experience into the last ten years adventuring in and around the North East’s waters. Hailing from Harrisburg, Pennsylvania he fostered a dream to leave the white snow behind for white sand and strike out into a second career in the maritime industry. Aboard his Pearson 30 he left Annapolis and headed South on a grand three month adventure which ended in Key West. He’s enjoyed a busy 35 year career as a professional musician, singer, songwriter & music educator, touring with several acclaimed musicians in North America & Europe. As acting Fleet Manager, Captain Jon oversees operations and occasionally will Captain a charter or two. He is a USCG 25 ton master and an ASA instructor for 101 through 114. Raised by a family of educators, Jon enjoys discussing the finer points of sailing with students & guests, and you may even be lucky enough to have him bring along his guitar for entertainment on overnight trip. Off the water, Jon can be seen at Smokin’ Tuna where he sings lead for Caffeine Carl & the Buzz, as well as playing Bass with other local bands.

Lead Captain Chris Toye hails from Pensacola, Florida and being on or in the water is life. Chris is a Certified Rescue Diver, major Surf enthusiast, Sailor, actively involved with non-profits Reef Relief & the Surfrider Foundation and he is passionate about sharing his love & knowledge of the ocean environment to his students and charter clients. Chris’s father encouraged him to take up sailing in his early 20’s, getting him aboard his first boat to try out crewing in 1992. He was hooked hard and was part of a busy race team for several years honing  his sailing skills. In 1999 he purchased his first vessel, and after fitting it out for offshore passage, departed across the Gulf of Mexico bound for Key West. A vision was sparked and he returned to Pensacola to take up a career as a professional mariner. He worked as crew on yacht deliveries and in 2010 he received his USCG 100-ton Captain’s license. He immediately returned to Key West where he conducted Ocean Eco Tours for many years, and continued doing long range deliveries. He has navigated the entire ICW, the whole of Florida, multiple trips to Belize, Mexico, BVI’s, & Bahamas. In 2016 he achieved his American Sailing Association Instructor certification teaching 101 through 114 multi hull and has kept a very busy teaching schedule ever since. He is very knowledgeable about ocean eco systems, animals and other topics which make for interesting nights at anchor. He is a gentle instructor, fantastic with kids, loves to talk about the world a large and is extremely safety conscious.

Captain Bob Solliday is a consummate professional yachtsman. He started sailing in his early teens on small lasers and Hobie-Cats and at just fifteen participated in his first oceanic crossing from Hawaii to Los Angeles, a journey of 21 days. After Cornell University and Graduate school at UCLA he jumped back into the ocean life and has been passionate about integrating sailing into his career ever since. He’s effectively sailed his entire life and gained experience on dozens of types of boats in all variety of conditions. He’s raced, cruised, captained & crewed literally hundreds of vessels up and down the West & East coasts of the US, multiple Trans Pacific crossings, sailed throughout the Caribbean and even took at 44’ Catamaran through the Panama Canal. He holds his USCG 50 ton master, instructs ASA 101-114, has been scuba diving for 40 years and is a private pilot. He’s a lively conversationalist and a sporty educator, with a great sense of humor. He takes immense pride in passing along his knowledge & passion for sailing to all who want to learn.

captain-randy-mullisCaptain Randy Mullis grew up on the East coast of South Florida where he developed his love for the ocean as an avid surfer. In 1999 while working as an Assistant Professor at the University of Wisconsin he was introduced to sailing through the Hoofers Sailing Club and quickly developed an unbridled passion for it. Over the following12 years sailing became a major focus in his life. Sailing almost daily, he garnered extensive experience racing and day sailing on more than 30 different makes of sailing vessels. In 2000 he took that passion to the next level and began teaching sailing on various size keelboats. In 2003 he took the decision to pursue a professional career in the industry, and in the endeavor to hone his skills undertook sailing adventures on his 43’ sloop on both US coasts, multiple blue water passages and extensive exploration of the Caribbean, He obtained a 50 Ton Masters credential, completed his credentials for all levels of ASA Instruction and a highly prestigious ASA Instructor Evaluator credential. In 2012 he retired as an executive in the financial sector, grounded Adventures on the Sea and transitioned from a part time to full-time sailing professional. Captain Randy teaches ASA courses, facilitates ASA Instructor Evaluation Clinics, delivers sailing vessels, captain’s charters and brokers used and new sailing vessels. He has conducted beginning and advanced sailing courses on the Great Lakes, St Vincent and the Grenadines, Ft Lauderdale, Miami, the Keys, and the Bahamas. He is a fine cook, an even handed and very experienced educator, and a Captain with the ability to put everyone aboard at ease in any sailing conditions with his composed & confident manner.



crew pic KWSA

Capt. James Blagg was trained as a Navigator on ships by the US Navy. He has crossed the Atlantic twice. James has served most of his time in the Navy in and out of the Caribbean learning the waters from Florida to Venezuela. While stationed in Italy James became a Master Scuba Dive Instructor for PADI while working with NATO forces. James love of the Ocean has inspired hundreds of his prior students to continue diving and some are now fellow Instructors and work in the Marine industry. Always pushing the envelope learning and inspiring. Captain James last duty station took him to sunny Key West where he currently resides. While stationed in Key West he learned the local waters in his sailboat and earned his 100 Ton Captain’s credentials. After retiring from the US Navy in 2013 james worked as a Captain on M/V Spree, a research and Dive vessel that frequents Dry Tortugas for 5 day trips. He has supported the functions of NOAA, FWC and several Marine University while researching Pulley Ridge in the Dry Tortugas National park. James last assignment took him on a 6 week Reef baseline survey of Reef system from Bimini to The Turks and Caicos Islands with Catlin Survey team. Captain James is always pushing to learn more about the art of Sailing, and stays very busy as a Charter Captain, while doing guest stints as an ASA 101 instructor.

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