Thanks for the thoughts and recommendations! I've got Last Stop Sports and BVI Watertoys on my list of people to talk to when I get to Tortola - Richardson Rigging is also a great idea for several reasons.

It's interesting how this trip is entirely unique and challenging from a packing and logistics perspective - its absolutely different from any other sail charter I've taken since the mid 1980s. Normally, I'd carry on a small backpack of clothes - in this case I have five 49.5 pound bags, a packed Yeti cooler (to become our onboard ice chest), plus large carry-on packs on each of the 3 of us traveling. But, I suppose its a different trip - regardless, the logistics have been incredibly challenging. (The packing process alone has taken a couple of days of packing, weighing, repacking, etc.)