Windsurfing Lessons on Montserrat: One of My Most Hilarious Travel Memories

One of my most memorable - and hilarious - travel experiences took place while I was visiting the Caribbean island of Monsterrat in the late 1980s. My mother and I were both tremendous fans of the rock band The Police, and knew that the band had recorded two albums on the island at George Martin's Air Studios. We had read an article on Montserrat in a travel magazine, and it had convinced us we should visit the island not just as a "musical pilgrimage" but to see its reported beauty for ourselves.

The article had mentioned a windsurfing instructor named Danny, who had supposedly given lessons to many of the island's visiting rock stars. Indeed, we found him on the beach at Old Road Bay within hours of our arrival on Montserrat. He was more than eager to share his stories and show us photographs of himself teaching Sting and other musicians from Rush, Dire Straits, and Duran Duran how to windsurf. We were originally going to stay on Montserrat for only three days, but my mother proposed we could extend the trip if I wanted to take windsurfing lessons from Danny myself. I eagerly said yes! Not only did it look like tremendous fun, but I could then go home and brag that I'd learned to windsurf from the same person who'd taught Sting, one of my musical heroes.

My lessons began the next morning, and suddenly it wasn't that much fun anymore. Just finding my balance on the surfboard was proving a terrible challenge. One of the first things I learned was how to fall off the board properly - going backwards, to avoid hitting my head. Every time I attempted to lift the sail and get a good grip, I lost my balance. After a few hours I was sore, tired, and frustrated. Danny said that was normal, but it still seemed as though I should be making better progress.

The next morning I began my lessons once more, not expecting to do much better. My legs and arms were covered with bruises from my falls. All I wanted to do was to be able to get on the board, properly hoist the sail, and learn how to catch the wind to travel a short distance. We were only a short distance out into the calm waters of Old Road Bay, which was nearly deserted except for my mother watching us from the beach.

Then it happened - I finally managed to lift the sail, keep my balance, and catch a short gust of wind. It felt wonderful! I loved to swim, and here I was skimming over the water with more speed and power than I'd ever had before. I only made it a short distance, but it was a genuine improvement. Danny encouraged me to keep at it.

I did, feeling increasingly confident in myself. I managed to get up and catch the wind once again, and this time I went blazing out away from the shore! It felt so good and I was so excited, I didn't realize how far I'd gone until I saw the sandy bottom of the bay beneath me turn into a rocky reef line. That was also when I realized something very important:

Danny hadn't shown me how to turn around yet.

I had a moment of panic. I couldn't tell how deep the water was below my board, so I didn't want to jump off and potentially hurt myself on the rocks and coral. I managed to lower myself carefully down to sit on my board and wave toward the shoreline for help. Fortunately, Danny was already speeding out on a surf board himself. My mother was also swimming out as fast as she could, but it was going to take an awful long time for her to reach me this far from shore.

My initial panic faded quickly as I sat and waited for rescue. Danny was laughing by the time he reached me. He hadn't expected me to get so good, so fast, either. He hitched his paddling board to the back of the windsurf board and "towed" me in to shore. My mother had given up on reaching us by then, but said how she had panicked when she saw me go out such a distance and was afraid I'd hit the stronger currents of the deep water.

That was enough windsurfing for me, that day.

The next morning the first thing Danny did was teach me how to turn around. By the end of my fifth day of lessons, I was doing fairly well sailing around the bay, cruising along the shoreline while being careful not to go out quite so far again. The trip to Montserrat was one of our most memorable Caribbean vacations, and my mother and I were fortunate enough to visit one more time before the island's long-dormant volcano erupted in 1995, causing great destruction and a radical change of life on the island. We hope to visit again some time in the future, although we know it will never be the same experience again.

Still, I treasure my Montserrat windsurfing adventure - and tell anyone who is considering taking lessons to make sure they learn how to turn around as soon as possible!