Hi Satsuma,
We've just booked our first family holiday to the Caribbean and I did lots of research.
Basically you need to set your budget and then decide between the "Hispanic" and "West Indian" islands. The first thing to note is that the "Hispanic" islands are considerably cheaper, especially if you're going all-inc and are therefore very tempting. You can briefly sum them up as"¦
Dominican Republic - Cheapest of the bunch, has some nice hotels (eg Iberostar Costa Dorada, Riu Merengue etc.) and has mostly shrugged off it's hotel food hygiene problems of the past. But be prepared for people to look down their nose when you mention it, it's definitely still viewed as the poor man's Caribbean. A few tummy troubles also still appear in reviews and you need to take the dreaded malaria tablets which don't agree with everyone.
Mexico - Cancun is party town and has some good hotels. Playacar is more relaxed and has the highly rated Iberostar Tucan/Quetzal. Lots to see, though may be a long way away, eg Chitchenitza and I think malaria protection is recommended if you go off the beaten track. The beaches come in for a little criticism, but otherwise the only downside I saw was that the American college crowd descend on the place in the holidays and it can become like a frat camp.
Cuba - I decided this was the best of the Hispanic bunch. Mainly European and Canadian visitors, superb beaches at Varadero, friendly people and some highly rated hotels such as the Iberostar Varadero & Playa Pesquero. You have to change your money in-country and a fairly long transfer from Havana to Varadero were the only downsides, but an all-inc. package at the Iberostar with Virgin flights was very reasonable and I very nearly chose this.
There is also Margarita, but I've just never really liked the look of the place, though of course that's not to say it's not worth a look.
We visited several of the "West Indian" islands as a couple and I would say that the most inexpensive is Jamaica. Plenty of choice of all-inclusive resorts, including three Beaches (Sandals' family friendly chain) which looked good. Jamaica has lots to see and do, but I'm not sure I'd recommend it for a first trip, as the hassle you get outside of the hotel is way higher than I've received on other islands and could put you off the region for life.
I much prefer the eastern chain of islands, such as St. Lucia and Antigua. Add to that Tobago, Grenada and Barbados and you've got the main players in that region. Not a lot to pick between them, but all-inc. like for like I'd say Barbados is the most expensive but probably has the most to see and do. I particularly liked the look of the Almond Resort chain, which have 3 hotels on Barbados and one on St.Lucia. Although the new St Lucia hotel gets great reviews, we've been to the island twice, so we eventaully plumped for the new Almond Casuarina Beach on Barbados. Slight worry that's it's still being built and the opening date keeps slipping but I'm sure it'll be fine .
If your budget is high (actually, make that very high), the Grenadines look absolutely fabulous. True desert islands, in fact I think they shot Pirates of the Caribbean around them.
By the way, December is a great month to go and there are some good bargains to be had in the 3 weeks before the Christmas rush when prices go loopy. It's also much drier/less humid in the December to April period which means less mozzies, in fact we never had a problem with bugs at all when we used to go during that period.