The first day of any charter means a mountain of responsibilities for the skipper and extended periods of hurry-up-and-wait for the rest of the crew. It can be a long, boring day for friends or guests hanging around, sweaty and anxious about starting their vacation after a long flight. With all that must happen before you untie the dock lines, it’s barely controlled chaos, especially for newbie skippers who are already juggling enough.

Some guests take matters into their own hands and head for the bar. Just like TV with toddlers, margaritas can be handy babysitting tools, but you want to your crew to be functional later. I speak from experience. Once, after stowing provisions with one particularly lubed and creative group, we didn’t find the toilet paper for a week.

As the responsible party, I’m usually swamped on the first day between tech and chart briefings, having boat issues fixed, and completing paperwork. A big challenge is to keep the crew and their endless requests away from the base personnel. I had a lady who insisted on swapping for stainless pans because they were presumably healthier than the Teflon ones on the boat. When the Tahitian girl on the dock responded only by blinking, the lady repeated her request with greater volume. Nobody needs to hear these first-world problems.

Frequently, as we prep the boat, I can tell the nationality of various crews on the dock by how they’re handling their own prep. The French find the onboard corkscrew and espresso maker in a flash. The Germans catalog everything, coiling and uncoiling halyards and tracing reefing lines. You don’t see the Italians so much as you hear them. And Americans just need to be entertained, or at least kept busy.

I’m a big fan of busy work because it gives guests a sense of purpose and involvement. And…let’s be honest, it also helps keep them away from the pitchers of painkillers and out of trouble. I’ve learned there’s no task too small not be useful, because “idle hands” and all that. Here are some of my go-to requests.

1. Sort out the chartplotter. Change the feet to meters and English to whatever other language you need. Greek can get tricky.

2. Have them fill water tanks you know are already full or nearly so. It usually takes 20 minutes just to find the fill, the key, and the overboard vent.

3. Assign someone the task of finding and testing all the keys aboard from dinghy lock to the companionway door. There are usually twice as many keys as there are locks and it’s a great exercise in problem solving, figuring out which keys are completely useless.

4. Get creative. I once got lucky with a soft-floor tender that needed to be unrolled and inflated. The separate floor insert was a consternation to the crew that swallowed an hour.

5. Ask for a detailed weather report from as many apps as possible. Everyone will jump on their phones and invariably be hijacked by TikTok and posting selfies on Instagram. Social media is better than beer for distracting adults.

Although it’s nuts, the first day is also useful because it gives you a sneak peek into your group’s personalities. You’ll get clues as to who’ll be willing to pitch in to cook and clean, or who can help fix a genset or a head. There will also be first glimpses into who’s most likely to dive deep into cocktails and then fight with their spouse, who’s prone to exaggeration telling you they were a lifeguard in high school but will nearly drown at the first snorkel stop, and who professes to be low key but needs the boat to be on a certain heading for the best tanning angle. Knowledge is power, and these insights are preparation for what could be a long week ahead.

You cannot cross an ocean without having the courage to lose sight of the shore. On charter, you won’t cross an ocean, but your first challenge will be losing sight of the marina at least. Once you’re through the first 12 hours, the rest is smooth sailing by comparison. 

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August/September 2024