My First Time Sailing by Leila Anderson

It was the early 90’s in Ft Myers, Florida and I was in my 40’s and fairly new to the area. There was a singles group that met on Sunday night at a local church. I had been going there for a couple of months off and on to make some new friends. There was an older man there named Bob, who was a sailor and owned a boat. He had a 17 foot Catalina Sailboat that he liked to talk about. I told my friend Gloria that I wished I could go sailing on the boat. Well she told Bob and he invited me to go sailing.  He kept the boat on Sanibel  near where he lived. I met him at his house and we rode on his Harley to the boat. It was midafternoon on a beautiful sunny day in March. I did not take my purse to the boat and wore my prescription sunglasses. Figured we would be back before dark.

We got to where the boat was docked. All the things we needed were on board except the sandwiches I brought. I was not sure what to expect. We climbed down from the dock and  boarded the boat. Then Bob started the engine. He gave me directions on how to cast off the lines of the boat. The lines were tied to a couple of cleats on a sea wall and the end of them went over cleats in the boat to hold it at dock and we left the lines on the dock. the dock was located on a vacant canal lot near the Sanibel bridge.

After I cast off , Bob motored to the Gulf Of Mexico, which was  not far away, while I sat on the bench seat in the cockpit. Once on the gulf there was boat was rocking hard side to side and that made me very skittish and left wondering if we were going to tip over. Bob noticed this and  explained that because of a heavy keel under the boat that it would not tip over and for me not to worry.  I

t was a beautiful sunny day, not too hot and with a nice wind. Once we were on the Gulf I held the tiller straight while Bob put up the jib sail at the front if the boat. Then he put up the mainsail. I was nervous trying to keep the tiller straight and keep the boat headed into the wind so the sails could be raised. Was scared that I would mess up and we would  have problems. It only took a few minutes for him to get the sails up.  Then he came back to the cockpit.

At this point he turned the engine off. The sails had caught the wind, the boat was heeled over to one side and skimming over the water. The wonderful quiet with the power of the wind moving the boat. All my tension drained away and I felt one with nature. It was an amazing feeling. It was spiritual Zen moment. I am a thinker and  my mind is constantly active analyzing things. At this point I was no longer thinking, just experiencing something magical that made me so relaxed.

We ate our sandwiches while sailing. We sailed even after it got dark . Bob was a very experienced sailor and knew the waters around Sanibel very well. In a sailboat it is important not to get into water too shallow and run aground. That would require a tow from another boat that happened by or a radio transmission to Sea tow and their coming to your aid. I had to keep wearing my extra dark prescription sunglasses at night as I am blind without glasses.

Suddenly there was a school of four Dolphins diving up and down next to the boat. They glowed with phosphoresce and glittered with a pale blue shimmer. It took my breath away. Looked at them both with and without my sunglasses to get full effect, while wishing I had my regular glasses to see better.

By now we were headed back and getting close  to the dock, so on went the motor again, and I held the tiller an pointed the boat into the wind while the sails came down , I was not as nervous this time.  Now that I knew the quiet of actual sailing ,found the sound of the engine running extremely irritating. When we got close to the dock I was given a boat hook to catch the lines on shore so they could be attached to the boat. Once they were attached to the cleats on the boat the engine was shut off.  Bob locked the boat up and we hopped on the motorcycle for the trip to his house. I thanked him for taking me sailing and headed home. Tired from a day in the sun and wind.

Driving home I Realized that sailing was something I just had to keep doing. It was such a fantastic experience. So calming and peaceful.  Now just had to figure a way to make that happen without buying a boat that I could not operate alone. Also, I now Understood that sailing a boat was complicated and required a sailing knowledge that I did not have. The motivation to be sailing again, was strong enough for me to get creative. After a couple of months  I figure out how to start a sailing singles club, which is a story for another time.


Leila Anderson


Living in many places over my life has led to some very interesting adventures.  From Alaska to Florida and many places in between. I am glad to now be retired in sunny Naples, Florida.