It had been raining for a week straight before my scheduled Friday sunset cruise with Captain Phil Brittain, owner of Charlotte Harbor Sailing, LLC.

I emailed him on Thursday evening and asked when he might be making a decision on whether or not to chance going on the water the next night. He emailed me back and said not to worry—the rain would be gone by 9 a.m. on Friday. I was more than a little skeptical, since I hadn’t seen the sun in days, and it was still cloudy when I got up on Friday morning. But sure enough, Captain Phil was right, and by 7 p.m. I, my husband and four of our friends were cruising with him out of the Isles Yacht Club.

The Captain has a 31-foot Catalina Cruiser named Eliora, which he uses not only for his charters, but also for lessons, to teach those who may be considering buying a sailboat and want to learn how to operate it.

As we cruised out into the Charlotte Harbor, he explained to us some of the things we were seeing and answered a lot of questions, from both me and from my friend Kristy, who has a motorboat of her own and wanted to learn about the Eliora. Captain Phil, having only lived in the Punta Gorda region since 2002, is very knowledgeable about the area and certainly about the operation of his boat. He and Kristy had a great conversation.

After we had tacked out a bit, the Captain deftly raised up the mainsail and adjusted all the ropes to try and catch some wind in the mostly still sky. He succeeded, and though we were moving very slowly, we were going. Quite honestly, I didn’t care that we weren’t flying through the water — it was such a beautiful, peaceful evening and the water was like glass.

Plus, there was a lot of room on the boat for us to wander around and Captain Phil even had a table that came down from the helm. That’s where we put our snacks and beverages. At one point, my friends Kristy and Heather and I were sitting up on the bow just hanging out while Captain Phil entertained the boys aft.

He seems to have the perfect personality to handle even a large group of spirited cruisers, like mine was. Very accommodating and calm, he made sure we all had a comfortable, enjoyable time. And though it was too cloudy to see a good sunset, we did get a nice look at the moon over the water.

On our way back into the Isles Yacht Club, Captain Phil told me a little more about his other aspect of the business — American Sailing Association certified sailing lessons. You can come take lessons from him on the Eliora, or if you already own a boat and want to learn how to operate it, he will give you lessons on how to sail your own boat.

I decided that even though I had a great time on Captain Phil’s sailboat, I had best leave the hard work of operating one to the pros. I’m thinking one of his two- or three-day cruises might be next on the agenda.

Debbie Flessner writes the Live Like a Tourist column for the Sun newspapers. You may contact her at


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