From start to finish, our sailing experience with Captain Rick was truly incredible. From the moment we stepped on board, we were warmly welcomed by Captain Rick and his crew, who made us feel right at home on the beautiful vessel. The boat itself was spacious and comfortable, with plenty of room to relax and take in the stunning views of the sunset over the Gulf of Mexico.

Captain Rick was an expert sailor and a fantastic host, sharing his wealth of knowledge about the area and sailing with us throughout the trip. He was also incredibly accommodating, tailoring the experience to our preferences and ensuring that we were comfortable and happy throughout the journey.

The sunset itself was truly breathtaking, with vibrant hues of orange and pink painting the sky as we sailed along the coast. We were able to snap some incredible photos to remember the moment forever. And, of course, the quality time spent with my fiancé on the boat made the experience even more special.

Overall, we had an unforgettable time sailing with Captain Rick and would recommend this excursion to anyone looking for a unique and unforgettable way to experience the beauty of Fort Meyers. Five stars all around!

Christopher Viscomi

What a wonderful day we had yesterday. Four of us spent the day aboard Fair Winds with Captain Rick and Sheldon, his crew. It was an important day for me, a thank you trip to three family members who have been caregivers and loving supporters during my recent health issues. We did a four hour afternoon cruise. Both Rick and Sheldon were knowledgeable, friendly and very competent sailors. When I lived in New England I had my own boat and sailed a lot. Crew and guests had a great time reminiscing about places we had sailed and boats we had sailed.
We brought a light lunch and ate it while sailing just inside of Sanibel Island. After that we were on one good point of sail after another. My three guests were sailing novices, and both Rick and Sheldon helped them to feel comfortable.
The vessel itself was pristine and well cared for, both above and below deck. The Catalina 39 is a very comfortable boat. With four of us plus crew it never felt crowded or like we were in the way of the crew. As I told Rick yesterday, I felt like I was sailing with a friend. It never felt” commercial or business as usual,” it was much more personal than that. It was a day that I hope I can repeat at some time. It was a five star experience aboard a a five star vessel.
Ken Smith

Ken Smith

What a wonderful morning! I had never been sailing and Capt Rick and crew made it a wonderful experience for me and my husband. It was so quiet and peaceful. Capt Rick was very informative. We will definitely be back next time we’re in town.

Cathy Gabrielle

My husband and I did Sun Sailing Charter early in February and this sail was by far the most memorable day we’ve had in a while. We sailed toward to Sanibel Island. We saw the light house in Sanibel Island and the Sanibel Causeway from the ocean. It was also very interesting to see furling the sail during our trip. It was a warm and sunny day which made a perfect day for sailing. Captain Rick and Sheldon were very knowledgeable and they pointed out popular places such as hotels. The captain even allowed me to hold the steering wheel and I was feeling to drive a sailing boat. What a wonderful experience.
There are two VIP seats which are perfect spots for taking beautiful photos. Definitely you should not miss it if you sail with them.

I would highly recommend them.

Ju Chou

Beautiful Day and the sailboat ride was peaceful. Captain Rick and Sheldon were very knowledgeable and friendly. It was a wonderful experience. I definitely recommend them

Ana Santillan

Captain Rick and his first mate Sheldon went above and beyond to make sure that we had a great experience sailing on the Gulf of Mexico. The boat was very clean and had plenty of room and more for the 5 of us, make sure you get to sit in the corner seats in the back of the boat! The weather was beautiful and the views were lovely, they even took us close to the Sanibel Lighthouse to get some good pictures. They were knowledgeable with the area and were happy to answer any questions we had about the islands we were near and give insider information on the best places to go in Fort Myers. I cannot recommend them enough.

Katie Doherty

Positive: Quality, Responsiveness, Value

Captain Rick and the crew made for a top notch sunset cruise! Definitely recommend Sun Sailing Charters if you’re looking for a fun activity in Southwest Florida


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

The captain very experienced, the assistants very friendly, we really enjoy our time. Thank you !

Wendywu .official

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

What a great overall experience. We were looking to sell our motor yacht and take up sailing, but hadn’t ever sailed before. So before switching styles, we decided to charter a day sailing trip. The whole experience was absolutely fabulous. Captain Rick even took the time to teach us the basics of sailing. We were desperately hooked on sailing from that moment on. Long story short, we sold our gas guzzling motor yacht and bought a sailboat and loving every minute of it.

Matthew Williams