Luxury Hotels - Caribbean Recommendations

I could use some recommendations for a Caribbean stay. I visited mostly the northern Caribbean a number of times when I was young but have yet to go back as an adult. My fiancée and I are looking to go and just relax for a while. She is a claustrophobe and has a fear of open water so scuba or even snorkeling are not priorities (though I'm still trying to convince her...). In terms of real stays I have been to PR and Jamaica. Via cruising I've been to St. Kitts, Martinique, St. Thomas, Guadeloupe, and one or two others. There are so many islands to choose from that I am feeling overwhelmed and could use some advice.

A few thoughts/priorities:
Excellent food
Privacy/Few families
Uncrowded beach

I am open to either cash or an award stay, though a lot of the chain properties seem to be the kind of all inclusive resorts I'd like to avoid.

My budget would probably max out at $500-600 a night (pocket change for this forum, it seems).

After more than 3 or 4 days of doing nothing I get very restless, so I was hoping I might be able to find an island where there are things to do. I'm open to doing more than one island.

I've only taken a cursory look around and liked the looks of Jalousie on St. Lucia (Wish I could afford Jade Mountain).

Thanks for any advice.

43 years traveling all the Caribbean regularly, my favorite two are The Viceroy on Anguilla and the Canouan Resort (formerly Raffles) on Canouan Island in the Grenadines. Both afford exactly what you are looking for and rates should be much lower after May 1.

Worldspan

Vieques PR. I go there often. I would recommend renting a condo rather then staying at the W however.

The Jamaica Inn in Ocho Rios, Jamaica. Go to the website. It is a divine holiday and I cannot recommend it higher.

The Jamaica Inn in Ocho Rios, Jamaica. Go to the website. It is a divine holiday and I cannot recommend it higher.

The Jamaica Inn is a lovely old school Carribean resort. The rooms are a little dated, but the verandahs are lovely. The food is average, but it is a great spot to vacation. If one goes, they have to book a room in the West wing. Watching the sunset while having a drink with a loved one in these rooms which are inches from the sea is a magical experience.

You may also want to look to a few very nice resorts outside Playa del Carmen. Aqua water, generally good service and Mexican food. Maroma, Esencia, etc. Good luck.