Hello Dane,
My wife and I have traveled to Cozumel, Grand Cayman and Little Cayman. If you have not experienced Carribbean warm, clear, crystal blue water you are in for a wonderful treat. As to choosing where to go, it depends on what you are looking for in your dive trip. For the all around value, diving and ease of getting to the island we believe Cozumel is the best. We live in Virginia and far enough away from the ocean to know what 52 degree water temp and 5 ft vis is like. We book our trips through Island Dreams(Houston,
http://www.divetrip.com). We stay at Fiesta Americana Resort Cozumel and dive with Dive House. Cozumel is a very safe and beautiful island. The diving is fabulous with water temp averaging 80+ degrees. The island is supported by tourism however, it is not overly commericalized.
Grand Cayman is very commericalized. The diving is great, beautiful reefs and marinelife, however it is very expensive to partake the island itself. Food and purchases are high due the the cayamanian currency value is greater than the US dollar. We stayed at Coconut Harbor and the accommodations are clean and nice. There is shore diving at this hotel.
Little Cayman is fabulous. It is a very small, non-commericalized island between Grand Cayman and Cayman Brac.
We stayed at Little Cayman Beach Resort and dove with Conch Club Divers. We highly reccommend you purchase the meal plans because the food at LCBR are five star. They will gourmet you to death, especially the desserts. You dive three tanks a day in some of the most beautiful reefs in the world. Conch Club Divers are wonderful. The only draw back to LC is the weight restriction on the flight(Island Air) over and back. About 50 lb weight limit on luggage, you can pay a over weight fee. If you carry your own gear this can be a slight inconvenience. Other than that it was well worth the price of the trip.
So, now it is up to you. For a first Carribbean trip my suggestion is Cozumel. After that you can do as we do after each trip,dream about future trips. The internet will give you all the information you can absorb. Dive magazines are also a source of information. It is a very hard decision to choose a dive destination. They all look sooooo good. Good luck. One word of caution and we found this out first hand after our first trip to the carribbean. It will be very difficult doning a 6.5 mil wetsuit or dry suit, hood, and gloves to dive you normal Seattle diving. The 80+ degree carribbean WILL spoil you.
Burt & Flo Jackson