Mother and Daughter Sailing Lessons

Jibe, tack and turn hard a-starboard on an unforgettable sailing vacation in Fort Myers Beach, Florida.


I suppose I should be ashamed of my secret satisfaction and relief at scoring five points higher than my 9-year-old daughter on our written sailing test. But after she trounced me on the live portion of the test, I had to salvage my self-esteem somehow.

Our tests came on the last day of an intensive five-day Learn to Sail class offered by the Offshore Sailing School at Fort Myers Beach in Florida during Sadie’s April school vacation. Each morning, we had classroom time for a couple of hours, where we learned sailing basics and terminology. After that, we went out on a 26-foot sailboat with our instructor for hands-on practice in the gentle waters off Estero Island.

About Offshore

The Offshore Sailing School was founded by Steve Colgate, a former Olympic sailor, who started the company in 1964 with his wife Doris. Also an avid sailor, she founded the National Women’s Sailing Association. Their headquarters are in Fort Myers, but they have seven other schools in the United States and the Caribbean.

Classes of different levels are offered, from beginner to advanced, most with no more than four students in a class. Sadie and I lucked out and ended up with no classmates at all. There was supposed to be a third person, but she cancelled, so it was as if we signed up for a private class. Our instructor Kurt Martin is a father of a 7-year-old, so he was used to kids and quite patient.

On Land

Our classroom was a small conference room at the Pink Shell Beach Resort & Spa, where the school is based. On display was a miniature replica of the Colgate 26, which we were to sail. Steve Colgate and a naval architect designed the Colgate 26 to be used specifically as a teaching vessel. In the classroom, at least, it looked fairly simple to handle.

Kurt showed us all the parts of the boat that we would need to know to pass our U.S. Sailing Basic Keelboat Certification test. The test is optional, but it is a great way to evaluate your skills and is the first step of a multi-tiered certification process that ultimately can end with you being able to charter your own boat. The class is pretty much taught to the 80-question test, and each day we’d get a take-home quiz to work on, plus some lengths of rope to practice tying knots. Of course, Kurt could show us a knot once and Sadie would have it down pat. I had her coach me at night and endured her sighs at my less-than-adept attempts.

On the Water

After a couple of hours of learning sailing terms, rules of the water and going over maneuvers on a whiteboard, Sadie would get antsy. After all, we could see the clear blue skies outside and knew another perfect sunny Florida day was waiting for us. Once we got on the boat though, she was completely happy and at ease. She took to it as if she was born to sail. Kurt was a calm and confident teacher and made us both feel very comfortable.

In no time Sadie was at the tiller, directing me, her crew, to trim the sails and warning she was going to tack or jibe to turn the boat. In order to pass the sailing test, you have to prove that you can rescue a man overboard, which involves a lot of boat maneuvering, so she got plenty of practice. Whenever it was her turn to “rescue” our man (a lifejacket), she was able to turn the boat around much faster and closer than I could.

Martin told me kids can be more instinctive and thus less afraid of mistakes, unlike many adults. I think he was just trying to make me feel better.

It was okay though. I was in awe of my 55-pound daughter, handling this 26-foot boat with no fear, laughing with joy as she pushed it faster and the wind whipped through her hair. As a confidence-builder, I can’t imagine anything better than this class.

Offshore Sailing School Programs

Besides certification classes, there are also a myriad of special programs, such as women-only, sail and dive, private cruising (for couples or families), single parent and more. You can opt for a stay-and-sail package at the Pink Shell, which is quite convenient. For a five-night stay and the class, the fee for one person is $2,225. A family package (two adults and up to four kids) is available starting at $4,615. More details on class options can be found at

Getting There and Where to Stay

Since the Fort Myers school is based at the Pink Shell (, it makes the most sense to stay there. If you fly in, I recommend getting a rental car. There’s no hotel shuttle, and a one-way cab ride will set you back $50. 

Destinations: Fort Myers Beach

Themes: Family Travel, Outdoor Adventures, Experiential Travel

Activities: Boating

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