...Just started diving about a year ago. Now 60 years old. Because of some physical limitations, valet style diving is appealing. Living in Chicago, there are not many nearby diving options. So my skills and comfort level will always be limited compared to those with hundreds of dives. Our first trip (Bonaire) was a local dive shop organized trip. I don't know if my experience was much different from others but the gap between my OW certification dive and this huge. Just setting up my gear was not exactly second nature. The group jumped in and took off. I found myself at 80+ feet and anxiously watching my air supply drain down. We now have about 30 dives but it's all still so new. So, you are correct that I've set some clear limits.
1. Most likely one dive trip per year (aside from one trip to Catalina or Channel Islands as our daughter lives in LA.
2. A great dive operator who will be understanding and helpful and not feel that we shouldn't need help.
3. A warm place to get away from the Chicago WINTER weather.
4. Ideally, I'd like to see a few of the islands but am not opposed to finding a regular place to go.
Hope that helps.
Thanks!
We are also in our 60s and live in Chicago. We have been doing warm water dive vacations for a long time but now we only do one dive vacation a year. I think that you would really enjoy the valet diving of Reef Divers Dive Operation at the Brac Reef Beach Resort (BRBR) or the Little Cayman Beach Resort (LCBR) that I mentioned in an earlier post. We have some physical limitations and we really appreciate that the valet diving is a normal part of the service. Not only do they do all the heavy equipment handling but they carry your gear to the back of the boat, help you get into it so you just have to stand up and do a giant stride and that is great for us.
During the dive you have the option to stay with the divemaster or go off on your own, whatever is comfortable for you. Both of these all-inclusive resorts are small and diver-dedicated and the food is great. The rooms and facilities are clean and comfortable. They have a tennis court, a coin op laundry, and a small spa too.
We like to spend 2 weeks in the Caymans. The first week on Grand Cayman (GC) relaxing and enjoying the amenities. From Chicago you will have to fly to GC anyway so why not take at least a few days to enjoy it? There is good diving off GC but we prefer the reefs of the sister islands so we mostly snorkel and do some shores dives when we are on GC.
Cayman Brac (CB) and Little Cayman (LC) are small and rural and very different from Grand Cayman so you can enjoy the different vacation experiences. But all 3 Cayman islands are clean and safe so you can drink the water and eat the food without concern and the local people are friendly. They also do a good job on mosquito abatement and have much lower rates of dengue and chikungunya than some of the other Caribbean islands and no problem with malaria.
The Bloody Bay Wall (BBW) off LC is some of the best diving in the Caribbean IMO; but there are good reefs and a sunken Russian Frigate off of CB that makes for a nice, easy, fun wreck dive.
CB and LC are both lovely spots but LC is more expensive and books up fast because of the attraction of the BBW. CB is cheaper, less crowded, and there is a bit more to do topside. The Caymans are an expensive destination but I think that the all-inclusive packages at the LCBR and BRBR are quite reasonable and they include almost everything: accommodations, food, diving, transfers, taxes, and tips. You just have to pay extra for liquor and tips for the dive op; and if you can book a "special" it can be a real bargain IMO, especially at BRBR.
When are you planning to go? You mentioned winter which is the high season all over the Caribbean. LCBR books up pretty quickly although they do get cancellations. If you don't get to visit the Cayman sister islands this time you may want to consider a trip for the future.
You should also consider your preferences for water temps. In the winter months the waters in the Caymans are very warm as compared to Chicago, but not as warm as the far southern part of the Caribbean, like Curacao and Bonaire. Good luck!