Dolphins are a common sight when sailing in the Harbor Crewed sailing 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.



Sunset Sails

Weekend and Extended Trips

Your Captains

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Island Sailing Publishing


Crewed Sailing Charters in Florida

Aerial photos of Island Dreams under sail Florida's Sailing at its Finest!
Let's Go Sailing! Island Dreams, our Catalina 309, is 33 feet of sheer sailing joy

Let's Go Sailing!....Go sailing with Naples' premier sailing charter company....Island Sailing. We offer many different sailing adventures from a two hour romantic sunset cruise to a week-long adventure along Florida's southwest coast or the Florida Keys. We offer dolphin encounters and nature — bird watching, Ladies Days, and multiple sail discounts. We cater to our customers' every need and strive to provide you with the best service possible. Give us a call to begin your sailing dream.

Your Yachts....

Island Dreams, a 33' Catalina 309
Every great sailing adventure begins with a great sailing yacht. We are now featuring our 2007 Catalina 309 "Island Dreams." She is 33 feet of sheer sailing joy and has all of the latest toys and conveniences including a Roller Furling Mainsail, autopilot, refrigeration, color chart plotter etc. She is safe, stable and really easy to sail and did I mention FAST!!!

Knot On Call is a sporty 34' cruising yacht Knot On Call is a Catalina 320 with a quick hull design that will fly along the beaches while allowing maximum comfort on her wide, clutter-free decks.

Introducing Knot On Call, a new Catalina 320
This sporty 34' cruising yacht is an awesome addition to our fleet. Her quick hull design will fly along the beaches while allowing maximum comfort on her wide, clutter-free decks. All the bells in whistles are included which makes her sure to please the sailor in the family. Safe and carefree cruising coupled with performance makes this yacht the perfect cruising yacht for the emerald waters of the Gulf of Mexico.

Both of our yachts have shoal draft wing keels allowing them access to cruising waters unreachable by other sailboats. Island Dreams and Knot on Call are definitely... “What dreams are made of.”

Island Dreams sailboat  available for charter

Your Adventure.....The sky (or the Gulf)'s the limit on your sailing trip as we truly personalize your adventure. Choose where you want to go and for how long and we'll work to make it happen. Don't know what to do???? How about a few suggestions....... Choose CREWED CHARTERS.

We apologize that we are no longer able to offer bareboat sailing, if you have not previously bareboated from us. You are welcome to sail our boats as much as you like with one of our fun and knowledgable captains.

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