First a home base (beach or landing spot) is picked where boat crews can take of from, and then return to on the last leg of the race.This home beach will work as the start and finish line. The course is set by picking out seven landmarks within the harbor or bay and designing a zig-zag course (with many of the legs set so the wind is on the beam for better speeds if the wind is light on race day). The legs should double back fairly closely on each other so that boats sailing to the first mark will pass fairly close by boats heading to the second. However the landmarks on one side of the bay must be spaced far enough apart so that two adjacent landmarks can't easily be seen in detail from one landmark to another.

Each skipper receives a chart of the course showng the landmarks and the sequence they're to be sailed to. Each landmark on the chart has a question to be answered about the landmark written next to it on the chart. It should be a detailed question that no one's likely to know offhand ("How many railing stantions are there on the west side of a bridge?" or the like. -Something that requires going there and finding out).
Before the race, each crew's boat is pulled up on the beach with sails furled (or tied up at the home dock). At the starting gun (we have used a carbide cannon on a wooden naval mount), the crews run to their boats and set sail for the first mark.

As soon as the lead boat wins its mark and its skipper writes the answer down on the chart, that boat is considered "Burdoned" and throws overboard a small float (no larger than a tennis ball) on a twenty-foot length of 1/8" nylon chord, with a 2' length of parcel string tied to the free end. This string is tied to the stern with the float towed behind as the boat heads for the second landmark, so that if the float is caught by another boat's hook, it will break free at the string. Each boat has its own color on its floats.

The following boats' crews can make a decision at this point. If they're close behind the lead boat, they can go on to the first landmark and get their own answer to the question on the chart, then try to beat the lead boat to the next mark. Or, (if they're trailing by quite a distance) they can attack the lead boat as it comes back toward the next mark, capture its float and, once they have the lead boat's float, they can demand that the lead boat's skipper tell them the answer to the first question. Then both boats can race to the next mark

Following boats can chose to break off from the first landmark leg and head for the second, with the plan of winning the second leg, then attacking and capturing the float to win the first landmark answer later in the race. No boat can break off and head to another mark on the same side of the bay (that is, you can only skip one mark at a time).

Whenever two boats reach a mark and get their answers within a minute of each other, it's called a tie, and both (or all) boats in the tie trail a float for that mark.
Two closely matched boats may chose to make it a straight race, with boat boats winning their own answers at each landmark. But, in a race where a gap develops between boats, the trailing boat(s) can then attack the leading boat heading back to the next mark and try to capture its float so the race can start even for the next mark.
A really slow boat may have to position itself for capture after every mark and hope they can somehow finesse the lead boat into a capture at the end, and make it back to the beach first.
First boat crew to beach and bring its chart back (with all answers filled in) and stuff it into the barrel of the starting gun wins the beer, the wenches, the first chance at the salamagundi, or whatever booty has been set as prize.

Here's a link to a great group of Piratically Minded scoundrels. They keep a weather eye out for trouble (so they can they be sure and get in the thick of it!), and do a good job of keeping their brethren informed with the newsletter "No Quarter Given". They maintain a site with links to sources of gear and other like-minded groups.

Click Here to get in touch with them!