A Sailing Dad Charters in the Caribbean

You’ve heard the stories and seen the pictures of sailing the West Indies, where three centuries ago, the real pirates of the Caribbean Sea hid treasure chests and marooned traitorous crew. I had too, and was enthralled. Ever since I started sailing more than two decades ago, I dreamed of a bareboat charter in those clear, warm, aquamarine waters, snorkeling with colorful fish I had only seen in aquariums, and sipping tropical drinks on white, sandy beaches under umbrellas.

As life went along, family demands and expenses relegated such a trip to a someday luxury. But as my kids entered high school, I became aware of their growing independence. I had to make this trip a priority if I was to share this dream with them and expand their world far beyond what mine had been at their age. Even if they were not hooked on sailing as I was, I hoped a trip like this would inspire enough interest in sailing that we could continue to share as they became adults. My wife and I started saving our money and getting the experience it would take to make it happen.

You see, I was not ready to charter a boat with only novice crew. True, I had sailed and raced on other people’s boats for more than two decades, including in some challenging conditions. (See “I’m Not Bob — The 99th Mackinac Race,” Latitude 38, September 2023)

I knew just about all the jobs aboard, but individually, not as a whole. I had seldom, if ever, captained a boat, and had never been responsible for the crew and vessel. I knew I needed to step into that role before captaining a bareboat charter.

We bought a trailer-sailer in early 2020. The boat fit our budget and landlocked location in Davis. We kept it at Lake Washington Sailing Club in West Sacramento, where our daughters had learned to sail in Sabots. Over the next four years, I learned, on a small scale, what it means to be in charge of a boat, including planning itineraries, repairing damage, maintenance, and instructing crew. I practiced launching and retrieving, docking, anchoring, heaving to, and crew-overboard drills, and my family became familiar with how to sail. Despite my self-confidence, I knew the charter companies would ask for more.

In 2024, I sold that boat and sailed aboard other people’s larger boats. I passed the American Sailing Association’s Keelboat Sailing and Coastal Cruising courses, then took the Bareboat Cruising course through Afterguard Sailing Academy in Oakland. For the next year, I led practice and fun sails with a different crew every month on the Oakland-Alameda Estuary and San Francisco Bay. I improved my skills by docking, piloting, planning, and working with people of varying skills and experience. These were the skills I would need to lead my family of unseasoned sailors in safely crisscrossing Drake’s Channel under sail and power, anchoring, picking up mooring balls, and docking.

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