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Let me begin by saying: I do not deplore all types of buddy boating.

If you want to move down the Intracoastal Waterway in the company of others, that’s fine with me—social buddy boating, restaurant pals. But if you are venturing beyond the horizon and you think there’s safety in numbers, then my message to you is: maybe, maybe not, because now you’ve become a committee.

Should we leave on Thursday or Friday? In the morning or at 11 at night? Should we plan on stopping at Black Creek or Little Farmer’s? Or should we go outside all the way to George Town? Should we check in with each other hourly or every three hours? Should we synchronize watch schedules for consistency? Should the faster vessels slow down so the fleet can stay together, or should each boat travel at its own speed with the resulting dispersal?

Consult, consult, consult.

The notion of the cruiser as a rugged individual seems quaint today. I would guess that half of all American boats go down island grouped together in yammering cliques. Like sheep, they flock for safety and a sense of community, but because they are not sheep, the goals are achieved at a cost, if at all.

The rest of us enjoy buddy boats for their entertainment value, as they bumble in and out of the anchorages, engage in small-group politics and, when things go awry, recriminate over the VHF radio. It’s astounding what otherwise nice people will do and say, and it’s amusing as long as no one gets hurt.

Fleet movements are a challenge even when conducted by navies. Navy captains are superbly talented individuals with the most brilliant among them leading the fleet. Tough, trained sailors under strict discipline man those ships. Fleet maneuvers are planned, practiced, rehearsed and practiced again. Regulations are developed based on decades, even centuries of experience, “written in blood.”

If a cruiser gang, for example, had one expert seaman to lead them, that wouldn’t be too, too bad. When Capt. Jack says “slow,” we slow; when he signals starboard 10 degrees, we turn. Aye-aye, skipper!

Unfortunately, buddy-boat fleets are governed differently. Say the smartest mariner in the group has a high-pitched voice. Watch as leadership defaults oh so gradually to the most assertive member, though the latter’s bluff and bluster may conceal an ugly truth: He’s not the sharpest tool in the box. No matter how lacking in judgment, he or she will also earn leadership points just for having been an airline pilot or for speaking with a British accent.

And that’s how mistakes are made.

Many experienced skippers have told me stories about having been roped into a buddy boat situation by cruisers whose skill levels were so low they became an unwelcome burden, some of whom had no business being out of hailing distance of TowBoatUS.

Most of the salts had basically the same idea about cruising with friends. It goes like this: “You headed south?” “Us, too, eventually.” “Isla Mujeres?’’ “Good. If you’re still there next week, we may see you.”

So much for consultation.

This article originally appeared in the January/February 2020 issue of PassageMaker Magazine.