Following the three-day Fast Track portion of the program, it was time to move out of the Mansion House and onto Offshore Sailing School’s brand new Hunter 49 for the seven-day liveaboard part of the course. This was by far the largest boat I had ever been on, and I was looking forward to sailing it. The boat was immaculate, and the Offshore staff had stocked it with all provisions we needed. Oh, and it had air-conditioning. There were four of us onboard: Mike from Offshore, Dad, a return Offshore student named Craig Econopouly and me.

While docked, Mike showed us how to check the oil and clean the pumps, all of which we were going to have to do every morning before we got underway. After the briefing, Mike motored us out into Tampa bay and turned the wheel over to me as he attended to the sails. “You’re sailing a 50-footer!” Mike said, and I thought to myself that I could get used to this, as I tacked the boat by simply turning the wheel—no more jumping from one side of the boat to the other or ducking under the boom. The feel wasn’t the same as the Colgate 26, but the dual helm stations allowed us to place ourselves in the most comfortable position possible.

We anchored for the night against the backdrop of the St. Pete skyline, and as soon as the anchor was set we cranked up the AC. I don’t think I could have made it through the trip without it. The next morning Dad decided to cut his trip short. His knees were bothering him and because we were right by the city it was a good place to get off the boat, so we dropped him off at the dock. After topping off our fuel tanks and waving goodbye to him, we headed southwest toward the Gulf of Mexico.

Craig and I took turns at the helm, sailing in 10-20 knots of wind to the Manatee River where we anchored in a small cove near its mouth to go swimming and take the dinghy to the beach. Mike’s morning lectures continued throughout the week, focusing on things like navigation, tides, anchor techniques and tying knots. Every day we learned more and more. We did a lot of motoring down the Intracoastal Waterway near Longboat Key, which I found nerve-wracking because of the moving sandbars. I constantly had one eye on the chartplotter screen and another on the water looking for shallows.

We spent a couple of days near LongBoat Key before we headed back to St. Pete. By this time I was feeling much more confident as we sailed toward Offshore’s marina. Although there is much more to learn, I now feel comfortable enough to take a boat out on my own. I’ve also had my first taste of cruising, and I can’t wait to get back out on the water. And, of course, I’ll never forget Mike’s sage advice: “Sail your telltales!”