I am posting this question for a wonderful Fireman friend of mine who moonlights in the ER where I work. This would be his first trip to the Caribbean. Here is the wish list.
1.Was leaning towards AI but is open to other ideas.
2. Budget $4000 for the week for 2, if not AI resort, would need to take spending money at least somewhat into consideration.
3. Would like something relatively quiet, no spring break type atmosphere, no casinos needed. Not tooooo touristy.
4. Prefers a more tropical island than flat coral based island.
5. Would like a nice beach, not rocky, but doesn't require "perfect white sand beach"
6. Good snorkeling would be a plus.
7. Would probably travel May or June, so low season prices may help with his budget.

He mentioned that he was looking into STL, but not sure if that is the best island for a first timer to the Caribbean. I mentioned STJ, but not sure if he would like staying at a place not on the beach and don't think Caneel or the Westin would be something he would like.

So, if you Fodorites have any advice for my good friend, I would appreciate it.

I'm looking into Provo in Caicos as my next "affordable" trip. Looking at $350/night at Sands, probably can do better. Just a thought. I would say Barbados, but ol' Sam Lord's is dead.

Tortola, bvi's...great laid back island and easy access(day trips) to the some of the other islands..Jost Van Dyke & Virgin Gorda.in fact Virgin Gorda would be a great island too...on tortola a nice place to stay is Long Bay Resort..www.longbay.com, i would suggest renting a car so they can tour and explore this beautiful island. there are so many beaches to go to and great places to stop and meet people !! also here's a website with some BVI info..www.b-v-i.com, we love these islands, VERY safe, relaxing,mountains,great snorkeling and never too crowded !!

Read up on St. Lucia. Steep mountains, lush rainforests, volcano, and black sand beach -- great snorkeling.

Where would he be traveling from? Airfare could eat a chunk of the budget.

provo is very much a flat coral island but has great snorkeling. no ai's but alot of great restaurants. st. lucia is not known for great beaches or snorkeling and i agree might not be best for first carib visit.
i do think the bvi's would be perfect for your friend. what about caneel/westin is out of character for them? to fancy? would they like the little place on white bay where the soggy dollar is - sandcastle? {www.b-v-i.com/jostvandyke} or is that too far in the other extreme?

They would be flying from the metro Detroit area. I have bee lucky to find airfare to my destinations in about the $500 price range with some shopping around. The reason for nixing Caneel is the price and have always read that the Westin was more family oriented. To me, STJ still seems like the perfect romantic getaway if they could get past not staying right on a beach. I e-mailed him a bunch of web sites to look at. Any and all suggestions appreciated!

EARLY May up to 3rd week or so will avoid rainy season in Caribbean. June might not be the best month for a first visit. Ladera on St. Lucia, the Port Antonio or Treasure Beach areas of Jamaica for a villa rental might be of interest or Maroma or Ikal de Mar south of Cancun on the 'Riviera Maya'.

You can also look into Curacao. It's not wild like Aruba but quite settled. The town is very interesting and the island was very safe. There was enough to do but not spring breakerat all. The all inclusive was a Breezes resort. We liked it. The snorkeling was great. There was only a small casino that wasn't a bother. We flew from Chicago to Miami and then direct on American.

Just got back from Virgin Gorda. Loved it. Would recommend Tortolla (long bay resort) or VG (bitter end) for your friend. Tortolla being more lush than VG. Very casual, not touristly. The budget should be fine for two for a week or so.

Montego Bay is an option worth exploring. Airfares to Montego Bay will be considerably cheaper than to any other Caribbean destination. Montego Bay is a beautiful destination with a great beach and a very definite tropical island feel. If he's traveling in May or June, I wouldn't worry about an overflow of rowdy college kids.

With the money saved on airfare, a greater amount of his vacation budget can be devoted to the resort and meals. Some excellent resort choices on Montego Bay include the Ritz Carlton and the Round Hill Hotel - both about as nice as any hotel you'll find in the Caribbean.

Just an update. He ended up deciding on a western Caribbean cruise. Not his first choice, but the price is right and some other friends are going too. He has made a folder for this and other web sites that I have sent to him. Said a nicer, more costly Caribbean trip is in the future, but is buying a home right now and wants a "getaway". Thanks for your responses.