We checked in from the south on Grand Turk, Cockburn Town. Real sleepy but very nice. You have to watch where you anchor because of the dive operators/reefs in front of town. We gunk holed our way north, checked out of Providenciales (Provo). There are 4 or 5 marinas there and pretty developed but good fishing in season not far from the marinas. Similar economy to the Bahamas ($$). Diving is a big draw. If you have the time, why not? You'll be there in the perfect time of the year. Not sure about free diving with a gun or a sling.
If you're going to stay in a marina then your choices on Provo are Turtle Cove and Blue Haven.
They both require you to come in throught the barrier reef out front. Not a big deal, either marina will send out. guide boat if need be. But if it blows up out of the North you can get stuck at the marina till the seas lay down.
Blue Haven is the old Nikki Beach property reopened. Nice marina with nice floating docks. Swim up bar at the pool. Lots of big boats. Far from town though.
Turtle Cove is more layed back and you can in most cases drive your rental car right up next to the boat. It is also very close to good shopping and supply stores. And you have several restaurants and bars with in walking distance. Carol the long time marina manager there will be glad to help you with whatever you might need.
There are some very good resturants on Provo.
Be aware electricity is expensive there.
The islands there have a very colorful history. Both in the distant and recent past.
If you want to get a feel for what the Bahamas and most of the Caribbean was like 50 or so years ago, head over to Salt Cay. You'll have to anchor out. But it's a cool place. And if you're there during the right time of the year the Humpbacks can come swimming right passed your stern while you're anchored up.
A great anchorage to stage from before heading over is Abrahams Bay in Mayaguana.
Im thinking South Side Marina, it's protected and doesn't have a barrier reef to get rough. Floating docks, and the AC reviews are 5 Star. Looks good, then we'll probably use the big tender to check out the near islands/cays near out. Also Blue Haven looks nice.
Hmmm......might need a high tide to get in and out of South Side. Not much there and you'll definitly need a rental car to get anywhere.