Is it worth waiting til the last minute to book an all inclusive to the Caribbean?

Millie, I was picturing February last night and had the exact same question!

I'm picturing end of November/beginning of December. Hopefully, there will be some responses.

Sometimes there are last minute deals with sunwing. Depends on time of year. You take a risk though, and might not end up where you wanted to go. If that's cool with you, you can chance it. Go look at what's on offer now to get an idea.

you can take a chance, sometimes you can get great deals sometimes not. I've booked for Cuba for the 1st week of December already as the prices were so cheap, wouldn't have got them cheaper closer to the date if I had booked last minute.

Have you looked at the prices now? If not, have a look and you may be surprised at what you can find.
If yes and you think it's too pricey, then wait.
All depends on your tolerance on not knowing really and of you have/want to go or not. If it's a scenario where you only go if the price is below x, then waiting is a great option.
Operators nowadays know more then 2 weeks prior where their soft periods are and with all these EBB(early booking bonus) promotion floating around till typically end of September, you can find some great pricing already.
What comes as last minute deals typically are what's left over that no one wanted so yes you will end up with a great price but your hotel quality will also reflect that. Other times, true enough you can get a kick-ass resort for a really good price but it may have come down from 1700 down to 1200 but if you want to pay $1000 (or less), these great resorts will never come this low. So if you aren't willing to pay up front for a great resort, chances are in a last minute deal situation, you won't be willing to either.
Last minute deals are more about filling seats onboard the aircraft them to fill hotel rooms. If the operator need to fill seats, they will offer a price with the lowest resort they can find as that is what normally moved the needle for them and accomplish their goal.
Hope that helps.

We always book a few days before so we can check the weather forecast for different areas.Then decide where to go. Jan is usually crappy on the East side so we have ended up in western Mexico more often than not. Never had a problem finding a flight and hotel last minute.

Where do you usually book through? I'm looking for deals the beginning of May

I'll look at redtag, sunwing, air canada vacations, I Travel, westjet. In the end I usually book directly with the whoever I am flying with. That way if there is a problem, I am dealing directly with them and not a 3rd party. It tends to be the same price anyway.

I've found the first week after new year is often a good time to book.