Yacht charter is an exotic proposal for many people, but bareboat groups are rarely made up of completely like-minded individuals. While some are perfectly content to sail at 3 knots all day posting on Instagram, others may be bored into sunburned unconsciousness if left alone on deck too long. For the skipper, safety is job one, but entertainment and keeping a happy ship are jobs two and three. You need to read the room every day and be captain, cruise director, instructor, and researcher all at once. Here’s how to wear the many hats with aplomb.
Few things make humans pay attention faster or complain louder than food. Eating on and off the boat is a make-it-or-break-it part of any cruise, so provision well, compliment the cook, and find lots of lunch and dinner spots ashore. Ask the base for recommendations, read everything, and make reservations. It’s amazing what you can find online or in a cruising guide, from cocktails at a wellness retreat to dinner in a local’s backyard overlooking the Mediterranean. These treats remain topics of conversation long after everyone has forgotten the lack of wind or the broken flipflops.
Special occasions add diversion to the charter routine. Just be sure to plan ahead. Having trouble finding a last-minute cake on an island in Croatia, I bought doughnuts to celebrate a crewmember’s birthday. Trying to make it a surprise, I hid them and didn’t tell anyone. The next day, the surprise was all mine because one intrepid sweets hound thought, “Oh, look, doughnuts!” The culprit was the birthday boy’s own daughter, which was funny. The single doughnut left for the group was less so.
Use a light touch when imparting knowledge, whether on sail trim or local history, because teaching a teenager or an alpha brother anything can ruin a vacation with lightning speed. Coming up with clever ways to get the info across can also be fun. In Tahiti, I devised the Chick Sail and the Dude Sail. One group managed sails, navigated, and anchored while the other made lunch and cleaned up. Then they switched. The conversation that night was lively. One lady just glowed with accomplishment. “That helped me understand and really get into this boating thing,” she laughed. “And I haven’t seen Bill do the dishes in 30 years.”
Chartering with kids adds another dimension. First, of course, is safety and keeping an eye on everyone. But second, and nearly as important to keeping a calm ship, is entertainment. Slow sails are like long car rides, so games like I Spy and 20 Questions come in handy when you see a tantrum coming. Nighttime can be especially challenging with kids because you can’t (or shouldn’t) just hand them a cocktail. Movies on an iPad or stargazing apps are lifesavers. Obviously, pirate ghost stories with a flashlight under the chin are fair game.
At the other end of the age spectrum is the mature set. Often embarrassed or uncomfortable with new experiences, older cruisers are just as prone to boredom as kids. Try to avoid a potential hip dislocation, but find ways to get them involved. In the British Virgin Islands, it took a bit of convincing and a lot of swimming on my part, but I had a boatload of seniors wrestling with the standup paddle board all morning. Soon enough, reluctance even gave way to competition. Waterlogged but delighted, they had climbed out of their comfort zones rather than sitting on deck applying sunscreen, and every one of them slept like a log that night.
Sometimes it takes personal involvement on the skipper’s part to nudge a participant. Near the island of Tahaa in Tahiti, one of my nervous crew shied away from snorkeling. After a half hour of pointers and persuading, I held his hand as we drift snorkeled through a coral reef garden. When he finally raised his head and spit out his snorkel, his face lit up. “That was spectacular!” he cried. “In all my 60 years, I had no idea that was down there!”
I’m often just a half-step ahead of the group, constantly poring over travel guides and websites to sound like a subject matter expert and historian. I use all the tools at my disposal, and I’m not above cherry-picking tourist brochures to give the impression that I’m brimming with local knowledge. I’ve been known to follow Greek panga vendors ferrying hotel tourists to hot spots and shooting guns on a tour of war tunnels in Croatia. Whatever works. Just make it spicy.
March 2025
