Private Sailboat Charters in Southwest Florida

Sail the warm tropical waters of the Gulf and you are one with nature.

“On a day when the wind is perfect, the sail just needs to open and the world is full of beauty.”

– Author William Ward

Enjoy the day on the Fair Winds, a comfortable, spacious and safe 39’sloop.

Have you always wanted to spend the day on the water?  Contact us at Sun Sailing Charter to plan your private charter.  The solitude and beauty of sailing has been around for generations. If you haven’t had the experience, now it’s your turn! Sailing on the warm tropical waters of the Gulf you are one with nature. Don’t be surprised to be in the company of manatees, dolphins, native birds or maybe even a sea turtle. There’s nothing quite like it as the simple sounds of the wind fills the sails while the water flows past the boat.

“Fair Winds and Following Seas” is a gesture of good luck to those we will miss and sailors who have served with honor and courage. The combination of phrases implies that a vessel will have good winds, and not have to pound into the waves. The phrase can be used as a toast or salutation between mariners. It is often used at a “beginning” ceremony such as a commissioning ceremony, as well as in retirement, change of command, or farewell ceremonies.

Our Cruises

Family Fun Cruise

Whether you are celebrating a birthday, graduation or anniversary, or if you simply want to spend some quality time together, Sun Sailing Charters is your perfect solution. 
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Sunset Cruise

The perfect way to end your day is aboard our comfortable, spacious and safe 39’ sloop watching the sun go down on a sunset cruise. 
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Sightseeing Cruise

From the beautiful picturesque shoreline to the exotic nature that surrounds you, a sightseeing cruise can help you escape from a hectic schedule and make you feel refreshed and relaxed. 
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Special Occasion Cruises

From birthdays and weddings to graduations and photoshoots, we have the perfect cruise to meet your needs.

SUN SAILING CHARTERS

The Ultimate Charter Experience

Meet the Captain

Starting at an early age off Cape Cod through retirement in Florida, Captain Rick has always been an avid sailor.  Some of his favorite places to cruise were Montauk, Shelter Island, Green Port, Rockland and Bar Harbor.  Of the boats I’ve owned since being in Florida, Fair Winds is his favorite, and he would love to share this sailing experience with you!

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Our Sailing Testimonials

Our good friends from New Hampshire were in need of a true Florida experience during their visit to Fort Myers and Sun Sailing Charters did not disappoint! Captain Rick and the crew of Fair Winds shared sailing secrets and surrounded us with nature as they tried hard to find some good wind out in San Carlos Bay on a sunny, 85 degree day. They regaled us with stories and shared bits of themselves so by the end we left feeling like we had a few more friends!
Thank you, Captain Rick and crew for a memorable sail!

Beth Bogen

We can highly recommend a sail with Captain Rick and his assistant, Sheldon. We felt completely safe and in good hands on this immaculate sailing ship. Captain Rick was kind enough to allow Dave, my partner to steer quite awhile and gave great instruction on sailing. Seating was very comfortable. Upon leaving, Rick’s wife gave us a couple treat bags- very sweet. We had a wonderful time. Thank you!

Laura Crampton

Ready for some Fun in the Sun?    Learn More About Our Charters!