Whether you need crew for a day charter, or a multi day sailing trip, we have a list of pre-screened Key West captains here for your convenience, or you can provide your own. Choose a captain whose profile fits your needs! They offer fishing skills, sailing education, spear fishing expertise, underwater photography, and even e-foiling! ALL are fully trained on our vessels and USCG compliant.

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Chris Staley

Chris is a licensed coast guard captain with 100 ton master with sailing and commercial towing endorsements. He has been an ASA instructor since 2007 and is certified to teach ASA 101, 103, 104, 105, 114, 118, and 119. Chris is a life-long sailor with experience sailing dinghies, beach catamarans, racers, cruisers, and cruising catamarans. He also has captained fishing charters and operates commercial marine assistance vessels.
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Justin Garreaux

Justin Garreaux was raised on the beaches of Charleston, SC where sailing, surfing and island hopping nurtured his passion for the ocean. Once he graduated with a computer science degree, he became a digital nomad and moved onto his sailboat with his 3 legged dog, Cooper. After a few years of exploring up and down the east coast, he set his sails for Key West in 2019. Since then, he has become incredibly familiar with the surrounding islands and reefs, snorkeling and spearfishing any chance he gets–it’s almost as if he’s been here his whole life. Justin obtained his USCG captains license so he could share these passions with others.
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Gregg Billman

Grew up on St Croix, USVI in the 1970s and 80s. Sailing since 14 years old….from small Hobies to 45’+ monos to 46’+ cats. Retired USAF: flew F-111s and F-15s. Retired defense industry VP (and corporate pilot): national security space industry. Currently living in Stock Island Village Marina with his wife on their 2006 Leopard 40 which they have owned since new, and have done extensive modifications to for eventual worldwide cruising. 100 ton master certified with sailing and towing endorsements.

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Jules Owen

Sea or sky, Jules does it all. She first moved to Key West 10 years ago to earn her 100 ton captain’s license. She has owned and lived on her own sailboat while captaining different catamarans and then spent 6 years sailing the Carribbean. For her next challenge, Jules received her pilot’s license and became a skydiving instructor. Jules also offers e-foiling lessons if you want to add on to your charter booking!


Ryzee Gardiner

Ryan (Ryzee) Gardiner was born in Key West and raised in Clearwater Beach. He grew up racing small sail boats before he made his return to Key West in 2015 to follow his passion for the wind and waves. Through the years he gained experience working on fast catamarans, sailing catamarans or various sizes, speed boats, and monohull sail boats to name a few. He currently possesses his 100-ton Master License with sailing and towing endorsement. When not working you can find Ryzee back on the water, spearfishing, wakeboarding, or hanging out at the sandbar.


Nathalie Meyers

Nathalie has sailed all of her life and has always had the passion to be a captain. Recently returning to Key West from sailing down the the Dominican Republic, she is ready captain again! She has a Bachelors in Journalism and Photography, a USCG 50 ton captain’s license with towing and sailing endorsements, and currently holds the International Underwater Spearfishing Assoc world record in the womens’ pole spear category. Nathalie is a talented underwater photographer, and her photography services can be added on to any charter upon request.

Rob Hummer

Rob Hummer

Originally from California, Rob has been sailing the Florida Keys for the last 3 years and lives aboard his own vessel here in Key West.  Rob spends nearly all of his time with his dog of 12 years.  During his time in Key West, Rob has worked for several water sports companies in an effort to earn his 50 ton captain’s license with sail and towing endorsements.  While finishing his college degree, he has built his own local business “Salty Paws” charters.  Rob is packed full of local knowledge both on and off shore and loves to share the local hidden treasures with our charter guests.

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Terry Minter

Terry grew up fishing and sailing along the Texas coast. His dream was to pursue a career in sailing full time. With a lifetime of boating and sailing experience on big boats and participating in over 200 inland and offshore sailboat races, the 50 ton masters license with a sailing endorsement was a snap. Looking for clear water, he landed in Key West where he fell in love with its people, the natural wonders of the Florida Keys, and the abundant opportunities to share daily adventures. Having never met a stranger and a great sense of humor, he fits right in to his new home in Key West.

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Josh Milat

Josh began sailing and diving at the age of 14. He has sailed the Red Sea, Carribbean, Mexican Coast, and much of the US coasts. He ran a dive shop and worked dive boats in the Red Sea for a time, and has captained sailing charters in BVI . During his time in Key West he has worked several of the major tour boats in town, and knows the waters and top locations very well. His plan is to circumnavigate the globe on his boat “Truth”.

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Jeff McGuirt

Early in his career, Jeff was an ocean life guard in Myrtle Beach, SC, trained in surf rescue and taught advanced swimming and life saving classes as a Red Cross certified instructor. Jeff has been a Key West charter captain since 1998 and has held his USCG Master license for 20 years. He enjoys racing, and loves to share his sailing experience with others. Our guests have shared with us that Jeff is a very good sailing teacher, who explains things well and with utmost patience.

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Jamie Huey

Jamie flew to Key West 11 years ago in his floatplane and started working on the water flying aerial tours. Jamie enjoys instructing many different skills and sports including, floatplane flying, skydiving, and paragliding. Now he is a full time eFoil instructor at eFoil The Keys, spreading the joy and excitement of riding an electric powered foil board. Jamie can offer eFoil lessons as an addition to your charter. Jamie holds a USCG 100-ton Masters Captain’s license with sailing and towing endorsements. He enjoys spear fishing and kiteboarding on his off time.