​​​​​​island sailing 
Naples' premier sailing charter company

contact us at islandsailingnaples@gmail.com  or  239.398.1483

Captain Gerard "Gerry" started sailing as a teenager in Long Island Sound and Newport/Block Island areas. Since moving to Chicago in 1988, he has been an avid racer, winning numerous regattas and participating in National and World Championships across the country, and he participated in the 2016 Conch Republic Cup race to Cuba.  Captain Gerry especially loves sharing his passion for sailing through teaching. Captain Gerry met Susan, his wife of 25 years, while racing. She was the competition and since have competed together and against each other, in addition to raising two wonderful boys who also sail.

Captain Mark, whose hometown is Colorado Springs, Co., has spent many years on the water.  As a 50T Master USCG licensed Captain, photographer, and as a certified scuba instructor, Captain Mark will gladly provide charter guests with diving excursions on their sailing trips.  Captain Mark is also a veteran of the U.S. Army.

Captain GERARD

Captain vinny

Captain Vinny, born in Spain, raised in New York, has spent most of his adult life living in Naples.  He has sailed for 40 years, 30 of which as a Captain.  He has sailed to Cuba and the Bahamas, and up and down the coast of the United States.


As a long-time resident of Naples, Captain Vinny is a wealth of knowledge and can share many interesting facts about the local area.​​

Captain Rob, owner of Island Sailing, has spent most of his life on the water.  As a child, he learned how to sail on the Chesapeake Bay from his father, a retired Marine Corps Colonel, who himself was a lifelong sailor. His favorite place to sail is the Abacos, Bahamas, where he's made countless crossings and he enjoys the crystal clear waters and secluded islands. Captain Rob has a passion for sailing and will gladly discuss yachting with anyone. Rachel, his wife, manages social media and publicity, and their daughter Kaitlyn is quite the little sailor. Both Rob and Rachel are also school administrators with backgrounds in working with children with special needs. 

Captain Marlena grew up sailing dinghies along the New Jersey coast. While in college in Boston, she joined the U-Mass sailing team, then taught sailing and navigation. Soon after starting her professional life, she embarked on a two handed sailing exploration of the world. Post circumnavigation, she taught sailing for several prestigious East Coast sailing schools. In 2002, she founded Island Sailing to bring an exceptional sailing charter experience to the guests of Naples and locals, too. During her time at the company, she wrote three nautical adventure novels. After handing the reins of her company to Rob and Rachel Dawes, she has been enjoying semiretirement by writing another novel and cruising the U.S. East Coast and the Bahamas. 

Captain Rob

Captain marlena

Captain mark