First timer Caribbean, where to go

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Another suggestion, this time in the US Virgin Islands (not the Lesser Antilles but worth a look) is St. Croix. It is a large island, with lots of undeveloped land, and they have a Hiking Society - see the link below.

I thought that the reef diving was very nice and that the Fredricksted Pier shore dive was easy and spectacular. Frog fish, seahorses, octopus, and lots of beautiful sponges and sea life in a gorgeous setting.

St. Croix Hiking Association

---------- Post added September 26th, 2015 at 07:22 PM ----------

I'm surprised no one has suggested Curacao. You can drink the water from the tap, very Dutch (with a Caribbean flair), nice shore diving, beautiful white sugar-sand beaches, no surf on entry. Really interesting coral formations. Nice warm water diving

I imagine that there are awesome hiking opportunities on Curacao, it is large and many areas are undeveloped and it is heavily wooded and quite hilly.

OP, I just want to remind you that these islands are very, very hot. When we go walking or bike riding in the tropics it is usually in the early morning while the air is still cool - or sometimes in the evening if the mosquitos aren't bad. But it is too hot and humid to be doing hard work in the middle of the day - at least that's my opinion.
 
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