Dolphins are a common sight when sailing in the Harbor Crewed and bareboat charters in Naples, Fla.

Island Sailing

Go sailing with Naples' finest and most experienced charter company
offering the newest fleet of modern, custom sailing yachts.

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Island Sailing Publishing

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Bareboat Sailing Charters in Florida

Beautiful tropical scene

Experience sailors can bareboat Island Dreams for a half or full day sail. Enjoy cruising along Naples' sugar white sand beaches aboard a fun and easy-to-sail yacht. She is well equipped for your daysailing needs.

Island Dreams' equipment includes roller furling main & 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.

We even have a fully carpeted cabin area and many decorative accents to make you feel at home. We have even included toiletries and sunscreen. Just bring your bathing suit and you're ready to go!!!

To qualify for a bareboat charter, click here!

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If we or 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.

MULTIPLE SAIL DISCOUNTS Want to go out sailing lots of times, but don't want to drain your wallet?? We have several multiple sailing discounts for our bareboat charters. The more you sail, the more you save!!! Packages start at $3000 for 10 sails. These sails may be used for half or full day trips. Call us for more details and bigger discounts on more sailing time.