Decided to write a trip report as the Forum's were very helpful in helping me decide where to go and plan the trip.
My wife and I went the first week of May 2016, which was perfect as it was after spring break and before any real possibility of hurricanes. Went from NYC direct on JetBlue and returned on AA with a quick stopover in North Carolina. We were limited with dates and I was planning very close to the trip so awards were hard to come by (certainly with Avios), but I think I did pretty well with CR points earned primarily with Ink Plus, Staples, and Serve. Anyway......
Arrival and check-in were a breeze. We brought packaged cold cuts and some bread. They did stop us at customs to check out packaged meat, and customs thought the hashgacha was a weird government stamp, but the whole process took 5 minutes and they passed us through with a smile. Cab from the airport to the Ritz-Carlton was 15 minutes and $25 American and was arranged quickly at the desk right outside the customs exit. I got the name of an ex-pat from the midwest who lives there now and will be waiting for you with a car if anyone wants to arrange pick-up in advance (feel free to email me). We came at an empty time so not really necessary.
HOTEL: Check-in at Ritz was also easy and my Marriott status got me a poolside room upgrade, but they were very stingy with upgrades to beach side rooms even though the hotel was clearly not at capacity. They would only allow what they called a "one-level" upgrade. So if you reserved garden you could get pool. Theoretically, if you reserved pool you could get beach, but....as I said they were not big on the upgrades no matter who I talked to. The hotel is both on the beach side and across the road connected by a bridge. It is really not a very far walk, but if you can't get upgraded to beach side I would recommend asking for a room on the main floor (same floor as main desk which I think is 3rd Floor) and close to the main hallway. This puts you at about a three minute, well air conditioned walk to the beach and pool. Rooms are very nice, certainly no complaints, but not the nicest Ritz room I have been in. Pool and beach are gorgeous, water is stunning, sand is clean and white, and staff is responsive. Staff kept apologizing for the "bad weather" since there were like 6 inch (not a typo) waves. Awesome game room for kids with every gaming system you can imagine on huge TVs, also there are separate gender spa areas. Beach was bigger than Westin next door and Ritz hotel itself was a bit nicer, although I can't vouch for rooms at Westin as I did not go in. You can get an extra fridge for no charge and they will empty out the mini bar fridge for you if you ask for extra fridge room for kosher food.
ACTIVITIES: We did not do all that many activities as the goal was rest and more rest. But we did do the snorkeling, stingray, starfish point tour. Based on prior tips here on the forum I reserved a double jet ski through Captain Marvin. The company was great and we got one double jet ski with a private guide. However, check the cruise line schedule before you go and plan for a day when there are no cruise lines in port as it becomes very crowded. Also, check the wind levels, if it is above 7mph I DO NOT recommend the jet skis. You are on open sea and it is VERY uncomfortable unless you are an avid jet skier going for action sports. Take the boat option. Trust me your wife (or whomever is sitting in the back of the jet ski will thank you). I got both legs vomited on and it was unpleasant
If the wind is anywhere above 10mph and certainly if ~15mph try to reschedule the stingray trip to another day. They won't close stingray city or snorkeling, and they'll tell you "it'll be fine" but it is very wavy, hard to stand and difficult to snorkel. Not at all like the nice calm, shallow pleasant experience it usually is. Starfish Point is an added snorkeling option and is a very nice quiet beach with beautiful sand, but there were minimal starfish and wasn't worth the extra money IMO.
The Turtle Farm was not worth it unless you bring little kids IMO. I'd rather be sitting on the gorgeous beach with a Caybrew (local beer, easy drinking, very decent). Bioluminescent Bay trip with Sea Elements was fun and worth it, especially if you have never done anything like it elsewhere. People at Sea Elements were super nice and reliable. Downtown Georgetown is nothing special either, but it can occupy a few hours of walking around if the weather isn't great.
Beach and ocean are awesomely beautiful in Cayman. Don't plan for many activities as there is not much to do aside from what I mentioned above (unless you like SCUBA or sport fishing, which are not our thing). Just relax and enjoy!
SHABBOS and KASHRUS: Rabbi Pewzner is very nice and super helpful. A couple of points. There was no minyan the shabbos we went (just a 'group davening') and the Ritz and Westin are a far walk especially in sunny, 90 degree weather with no eruv. We were going to try it anyway as I can't turn down a good kiddush, but my wife wasn't feeling great. There is a lot of kosher food in the Foster's right near the Ritz and Westin in The Strand Shopping Center (bread, cereal, tuna, chumus, lox, etc), but they did NOT have kosher grape juice and the wine store in the plaza did NOT have kosher wine. Rabbi Pewzner mentioned they do carry these items, but this is apparently only intermittently so don't depend on it. I would call the supermarket in advance and check before leaving the US. I did that and they had one bottle of Kedem GJ left over from a Pesach display that they held for me. Oh....and you can fill up your wagon at the The Strand supermarket, pay, and then walk out of the store with your wagon, walk back to the Ritz or Westin (~5 minutes) and then just leave your wagon on the street! The island has a service that picks them up later that night. In fact I recommend this method if you are going shopping as it is easy and less expensive then getting a cab for a 5 minute walk and having them wait for you.
DO NOT get the kosher prepared meals from the Ritz, they were very expensive and INEDIBLE. They came double wrapped on china, but that was the only good thing about them. Only got one breakfast and a lunch before giving up entirely and using the food from home and supermarket.
The fridges in the Ritz have a light that is turned on/off when the magnet on the door and on the fridge light are separated/connected so you can't just tape down a button for shabbos. However, you can slide the entire light fixture inside the fridge out of it's frame (use a little muscle) so that it remains separated from the door magnet at all times. This worked for us very nicely for shabbos and it slid right back in on Saturday night (I am not offering warranties or step-by-step instructions, just saying it is possible).
Feel free to email with any questions.
-KEG
