You didn't say where you are chartering...I'll assume by your last sentence that BVI and USVI are considerations. My Vote would be for BVI, for it's safety both on water and land. Sailing is relatively easy, line of sight and in pretty protected waters ( Drake Channel). I'd stay in the BVI and not deal with going and coming through customs more than once.
Regarding size...I've chartered the moorings 47 ft cat..with 4 cabins and 4 heads.
with 6 a few times.. We found it very comfortable..we use the extra cabin for luggage etc.
The 4 heads are great. You will probably be comfortable on the 40.. as well..
The 47 had a generator and AC....which was nice to have for a few hours each day..
getting dressed for dinner..and having cocktails..;-)
With 8...you might have to make a few trips in the dinghy to shore.?
The salon table probably won't sit 8...around the table. ( but the captain and the host? can eat on deck..? ) Probably the only time that would matter is if you made dinner on board..
Breakfast and lunch are usually very casual...we head to shore for dinner most nights..I think maybe we had 1 or two dinners onboard.
What's the function of the Host? Is that person preparing meals, snacks coctails etc?
I wouldn't worry too much...it's paradise...like you say..you just roll with it.
Sunning on the trampoline..was the favorite activity of ..the admirals...on our boat..
Last edited by Tempest; 09-29-2011 at 12:05 PM.