Special Occasion Cruise

Make your special occasion a day to remember with a sailboat cruise with Sun Sailing Charters.  The solitude and beauty of sailing has been around for generations. If you haven’t had the experience, now it’s your turn!  Sun Sailing Charters offers three different charter excursions giving you the opportunity to celebrate your special occasion while enjoying the beauty that Southwest Florida’s Gulf Coast has to offer from a different perspective.

From birthdays and graduations to anniversaries, weddings and more, Sun Sailing Charters is your perfect solution.  From 1/4 day sails, 1/2 day sails to sunset sails, you, your family and friends will have a fabulous experience with lasting memories to last a lifetime!

Special Occasion Cruises Offered by Sun Sailing Charters

  • Anniversary Celebration
  • Engagement Surprise
  • Wedding Ceremony
  • Bachelor, Bachelorette Party
  • Graduation Party
  • Birthday Party
  • Burial at Sea
  • Special Date
  • Photoshoot
  • Family Fun


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, Resolute is his favorite, and he would love to share this sailing experience with you!

Learn More About Captain Rick >

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