We're looking to take a much-needed vacation to the Caribbean in the middle of May. We are on a tight budget. Is there any way to visit the Caribbean, preferably the USVI, but I'm open, for under $2000 with air? We're flying from FL, so hopefully that will save us a little money on airfare. We want lots of relaxation, with some sightseeing if we want.

I have been checking prices during that time frame to Negril Jamaica and you could go for a week and stay, for example, at Coco La Palm (a very nice property) for less than $2000 including air. There are other places that are nice that would be even cheaper. This will probably include breakfast. You are so close that you could easily be on the beach the afternoon of the day you arrive. That doesn't include food but it is cheap in Negril and there are plenty of excursions you can take. I used a Florida based travel agency last year for my trip and they were great. I found them at www.escapetoeden.com They book both AI and non AI.

There are some good value cottages on St John which is the key to staying within your budget. You'll need to rent a car so that budget's tight. Check these out:

http://www.bananawindcottage.com/

http://www.bookitvi.com/kokomo.htm

Have you thought about the Abaco islands, only 1 hour away. Explore and visit many islands in this area. Deep-Sea fishing, great restaurants, private cottages and water ferries. Only a few weeks left.

visit www.summerviewcottage

Have you considered a cruise? Could easily do that under $2,000 and save on air by driving to the port. Tons of relaxation and could pick one that stops at St. Thomas, etc.

Just got back last week from St.Croix. It was very relaxing and not too "touristy", with no criuse ships it's not crowded. We stayed here http://www.hotelonthecay.com/index.php
it was very reasonable, it worth checking out.