What's the best place to dive & increase logged dives in the Caribbean? (during December or in general)

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As mentioned above, a $1,095 Blackbeard's liveaboard from Nassau, Bahamas would be a great choice. Realize that is your lodging, food, and up to 19 dives for that price. My son (13 at the time) and I went on Blackbeard's with only 9 prior dives each, and it really helped us progress our diving. You really can't beat the total cost-per-dive for anywhere in the Caribbean (flights are usually pretty reasonably priced compared to Bonaire, Curacao, etc.) and the diving is pretty darn good. Actually, the food is pretty darn good too, especially considering the galley (kitchen) is tiny.

Cozumel could be a good option -- you could do 2 tank boat dives for around $100 or a little less with a 5 day package from some dive ops. Combine that with staying at a hotel (Hotel Cozumel, Blue Angel, Barracuda, etc.) with on-site shore dives for the afternoon or evening, and that could work nicely. Shore dives there are not tide dependent.

I'll throw one more out that is not normally top of my list, but still pretty good and perhaps good for your goals -- St. Croix. If you stay in Frederiksted, you could dive the Pier several times a day, and it is not tide dependent -- and super easy dive as long as you just follow the pier columns out and back. There are also boat dives available from Frederiksted. Frederiksted is a very sleepy town, but the Pier dive is exceptional and I could probably be happy going a week and only divinng the Pier multiple times a day and at night (great night dives there). One caveat is to check the cruise schedules, since you can't dive the Pier when there's a cruise ship docked there (most still leave early enough you can get a night dive in). Another caveat is overall St. Croix is a bit more expensive than Cozumel, and not many topside activities there if you just stay in Frederiksted (and need to rent a car if you don't).
 
Agree with @Rob9876 about St. Croix (was going to suggest it myself but he beat me to it.) Another nice thing about St.Croix is that if the Pier isn't available, one can drive to Cane Bay for a shore dive (or boat dive) of a wall or can head across the island (25-30 min) to dive the Salt River area or sites nearer Christiansted. With the Frederiksted Pier, wrecks, reef, walls, and canyons, there are lots of diving options!

I would say there are enough top side activities to keep one on the go for a week. December may still have the Christmas Boat Parade! Things to do might include a Cruzan Rum Factory tour, the St. George botanical garden, the Whim Estate and Sugar Mill, ATV tours, the Lost Dog Pub (with white sauce pizza), taking in the Christiansted boardwalk, catamaran and snorkel at Buck Island, Point Udall (the easternmost geographic point of the US), Sandy Point beach (where Andy met Red in the movie Shawshank Redemption), a hike to the lighthouse on Ham's Bluff, and a casino. There's other stuff to do but those things came to mind.
 
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