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 mark

Captain Mark started sailing a long time ago, 1966, in Puerto Rico, on his dad's 25' cutter. Since then, he has sailed in a variety of places like Puget Sound in the Northwest, Grenada in the Caribbean, Cazumel, Mexico, Tom's River, New Jersey, and much more. Until 2014, he was employed as a mortgage banker, but his undergraduate degree is in Limnology, so he worked at MSU's research lab on Lake Michigan for a season before completing his MBA at Northern Michigan University. Since 2014, he has taken his trawler from Naples into Canada twice and completed the Great Loop and the Triangle Loop. He enjoys meeting the people who charter with us at Island Sailing and he has experience in the Everglades which helps to explain the local wildlife. Most of all, he enjoys sailing and helps his passengers get enjoyment from it as well.

Captain marlena

Captain Rob

Island Sailing - Naples, FL​​

Captain marty

Captain Markwhose 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.  He enjoys extended day and overnight trips, and sailing up/down the FL coast, including the Keys.  Captain Mark is also a veteran of the United States Army.

Island Sailing Naples | 800 12th Avenue South, Naples, FL | | 239.398.1483

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 the company to Captain Rob, she has been enjoying semi-retirement by writing another novel and cruising the East Coast and Bahamas. 

Naples' Premier Sailing Charter Company