Agree with Citruspers...the DSLR would be worth it only if you're really wanting to get into photography, and learn to get the most out of it, or if you intend to be shooting often in challenging situations...otherwise you're just getting a bigger, heavier camera and likely as not getting the same basic results you'd have gotten from the pocket cam. In normal, good, daylight, even a basic P&S camera can do fine - and there's plenty of light in the Caribbean. Flash shots at the dinner table of the family or friends will do fine too - not professional portraits, but fine for the memories.
If you really think you'll be encountering low light situations often, want to go handheld, will be shooting in situations where you might want more dynamic range, will be cropping a lot, etc, then those mirrorless interchangeable lens cameras can be a good solution that sits between DSLRs and P&S cameras, with the size and portablity closer to the compacts (without purchasing the really long lenses), yet with the image quality and high ISO ability closer to the DSLRs. Sony NEX, Olympus Pen, and Panny G series all worth a look in this regard.
The S95 and LX5 are both slightly better than other P&S models due to their larger sensors - though 'larger' is relative, since compared to mirrorless cams and DSLRs they are still tiny sensors. And they offer a little more manual control for those willing to learn a bit and want some control over their photos. Add the Samsung TL500 and the newly announced Olympus XZ1 to that list as larger sensor, manually controllable cameras.
Personally, I love having my DSLR when I cruise - but I really am into photography, and like shooting lots of challenging scenes - handheld night shots, HDR, action and birding, live shows, etc. These are areas where the DSLRs come into their own - but DSLRs are heavier, less portable, and require investments in lenses to really get the most out of them - to really reap the benefits, the kit lens and Auto mode won't get you much farther than a good P&S, other than being more capable at higher ISOs.
Sony DSLR-A580 / Sony 18-250mm / Minolta 50mm F1.7 / Sigma 30mm F1.4 / Tamron 10-24mm / Tamron 150-600mm / Tamron 90mm F2.8 macro / Minolta 300mm F4 APO
Sony A6000 / 18-55mm F3.5-5.6 / 55-210mm F4-6.3 / 10-18mm F4 / 35mm F1.8 / 16mm F2.8 / via manual adapter, lots of Pentax K mount, Konica K/AR mount, and Leica M mount manual lenses