The old adage, "take less clothes, bring more money" doesn't necessarily mean you have to bring more cash but rather most Caribbean travelers end up spend more money than they originally budgeted and they end up not wearing all of the clothes they packed. For the average 7 to 1o day visit you should be able to pack everything you need in one standard size 21" roll-aboard and one personal size carryon per person. You actually don't need a lot of cash, as credit cards are widely accepted and you can use ATM's to get more cash during your trip, if needed. In over 40 years I've traveled all over the Caribbean and much of the world and rarely carried more than the equivalent of $150US in cash at any one time. On most days I've left the bulk of it in the room safe and carried only a small amount for gratuities, taxi fares and sundries. I relied on credit cards and used ATM's for cash when needed. As for packing light, here's a tip; A few days before your departure lay out all the clothes you think you'll need in a spare room. Admire them and congratulate yourself on your fine sense of fashion then put half of them back in the closet and pack the rest. Don't worry, no one will notice what you are wearing or if you've worn the same outfit a few times.