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

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). 

Send us your sailing resume, and we'll schedule a time to evaluate your sailing and navigational skills to ensure that you can set up the vessel and navigate through the channel and in the local sailing areas (Naples, Marco, Fort Myers, and Sanibel).  We'll show you how to set up Island Dreams and how to stow her away at the end of a sail (docking).

For those using our packages, we look to complete all of the sails within a 12 month period and only accept ten boat club members at a time, to ensure availability.  Boat club members have priority over regular captained charters when scheduling.

​​​Bareboat Prices:

  • Half day (4 hours):    $450

  • Full day (8 hours):    $700

Boat Club Packages:

  • 5 full day sails:    $2,250 *
  • 10 full day sails:  $3,750 *

* Day sails only, not to be combined for multi-day sails

​​Prices subject to change and do not include tax.

What is a bareboat sail?

Island Sailing - Naples, FL​​

What is the boat club?

Naples' Premier Sailing Charter Company

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.  Up to 6 guests are permitted.

Island Dreams' equipment includes roller furling main and jib, color chart plotter, autopilot, VHF radio with RAM microphone in cockpit, bimini, and swim platform. She has raised stern rail seats and wide decks for maximum lounging area.

​If you feel your sailing skills are a bit rusty, you may want to take a captain aboard for part of your charter. This is a great way to brush up on your skills, take some pressure off while you orient yourself to the boat, and get some great local knowledge.​​