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[quote=MN3]this is a deep rabbit hole with no great solution as far as i found.  I have tried dozens of methods. From: homemade pvc cup holders (which did work pretty well), velcro/cloth beer holder (secure on the side stay), to swinging cup holders below the boom - they all fail in some way or multiple ways. Things under the boom get snagged when tacking, same with most hanging side stay cup holders.

I went so far as to crimp a bead (like the hobie16 uses with a fork  aloft to set the forestay) so i could elevate my beer holder (bad idea for your / crews hands). most get wet when you tack and don't have the ability to take your drink with you (this is a balancing act when sailing solo, with jib and maybe spin), some fall overboard.

I ended up using a well secured cooler with a velcro lid flap near the mast, and in a coordinated 2 second burst: I drop the mainsheet (or put it in my teeth) open the lid, grab the bottle, twist open the top. take a swig. put the lid on bottle and twist, get in cooler, close lid, secure velco and then ... swallow my rum ....

- ymmv[/quote]

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