1/2 day (4 hours):    $400*

Full day (8 hours):  $600*

5-day packages:      $2,000*

​10-day packages:     $3,500*​

* ​prices subject to change and do not include tax

WHAT IS The BOAT club?

Want to go sailing but don't want to pay the high costs of owning a sailboat?  You can!  Join our boat club and save thousands.  At Island Sailing, we can get you on the water for less than you would pay for dockage.  

Our bareboat sails cost:

  • Half day (4 hours) - $400
  • Full day (8 hours) - $600

Through our boat club, we also offer two packages:

  • 5 full day sails  - $2,000   ($400 per day)
  • 10 full day sails - $3,500  ($350 per day)

How does it work?  To begin with, we 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).

Next, we show you how to set up Island Dreams and how to stow her away at the end of a sail (docking and putting away the basics).

Now that you are ready to sail, just let us know when you wish to reserve Island Dreams. 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.

Want to string days together for overnight or extended sails? Trip to the Keys?  You can do that with the boat club at no extra cost!

Email us at islandsailingnaples@gmail.com for more information.​​​

Island Dreams

bareboat/Boat Club


Experienced sailors can bareboat Island Dreams for a half or full day 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.

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.

Email us at islandsailingnaples@gmail.com for more information.

Interested in bareboating with Island Sailing?  Email us your sailing resume and inquiries at islandsailingnaples@gmail.com.



boat club pricing 

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

contact us at islandsailingnaples@gmail.com  or  239.398.1483