Naples' Premier Sailing Charter Company

Island Sailing - Naples, FL​​

We offer many different captained private sailing adventures, including 2, 3, or 4-hour sunset sails and day sails, overnight/weekend trips, and week-long adventures along Florida's southwest coast, Florida Keys, or to the Bahamas. Enjoy a bay tour, set sail in the gulf, and enjoy what nature has to offer aboard Island Time (47' Beneteau) or Island Dreams (31' Catalina). Be on the lookout for dolphins and various FL birds! We cater to our customers' every need and strive to provide our customers with the very best service possible.  Let your captain be your tour guide on your private charter. 

​Captained charters

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

bareboat/ boat club 

Experienced sailors can bareboat Island Dreams, our 31' Catalina, for a half day, full day, or overnight sail. Enjoy cruising along Naples' sugar white sandy beaches aboard a fun and easy-to-sail yacht. She is well equipped for your sailing needs.  Want to go sailing but don't want to pay the high costs of owning a sailboat? You can! We also offer a boat club (5 and 10-day packages). Combine your days and take her out for overnight trips!