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Help me! I'm new at booking vacations!!

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Thanks ahead of time for any help and advice. My wife is gonna be 50 this year. After a nice party with family and friends, I was thinking about booking a 10 -14 day trip to an island in the carib. Now, ANY AND ALL previous trips were researched, planned and booked by my better half. I want this to be a surprise. And I am spinning my wheels.....just when I think I've found the perfect place, something comes along and bam! I'm starting over again.

So, were 50. Not dead, but I couldn't spend the whole time exploring mountains, either. I'm looking for decent amounts of activity BUT real nice beaches, nice hotels or villas, fishing, shopping (but we are NOT shopaholics.) I guess beautiful blue water, some fishing, some sights, and a real nice place to stay are the most important. I would be more inclined to "rough" it a bit than my wife....and this IS her present.
My budget? Since I've never seen what we've spent in the past, I really don't know what is a little or a lot (like I said, my wife always did this) I guess 5 grand apiece for air and hotel is cool. I really want this to be a nice time for her and I HAVE GOTTEN IT DOWN to 4 islands..........I think......... but I'm open to ANY advice.

In order of what sounds the best....Barbados, anguilla, st lucia, st kitts and grenada.....oh, thats five, sorry. Sorry if I sould totally lost, but I AM!! Any help from the experienced?? Thanks I appreciate it.

PS. We gone to Aruba and Hawaii only. Traveling was always so expensive...but things are much better and I would LOVE to travel regularly...The stories I read here truly sound wonderful...Thank you.

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