when are you looking at going?

Also, your budget will play a big part in the decision.
Some Caribbean islands are fairly reasonable, whereas others can be incredibly expensive.

It will be July August (kids hols).

Haven't got loads of money but middle of the road sort of cost - can do DIY no problem.

We in similar situation, are going to Carribean for 1st time and taking along 17 YO daughter.
We are going to Tobago, found it lot cheaper and not so commercial (spoilt) as a lot of other islands.

We are going DIY, flights with BA and apartments we found on other (specialist) website. Not sure if I allowed to name names, but is called My Tobago.

Good luck.

Hi - we're also going to Tobago -going 4th December for 2 weeks so arrive back on 19th @ 9am after an overnight flight!
Going with a company called http://www.letsgo2.com - good choice of resorts, hotels even airlines and you can upgrade to premium, (which we did - with Virgin!) business or first (I wish).
We're staying at Bluewaters Inn in the north of the island and have upgraded from a standard seafacing room to a 1 bedroomed apartment - looks really good.
And I agree with seagull re commercialisation (lack of).
Everything i've read reinforces this and having looked on many tour operators websites , have found only a very few actually feature tobago.
So here's hoping!!
Terri