I loved the Marriott on Seven mile beach. It was about $270/night. I went there to swim so I shared the room expense with a friend.
Sent from my iPhone using Tapatalk
The problem with the Marriott is that they have essentially lost their beach due to erosion. They are negotiating (unsuccessfully) with the local government as to how to mitigate the problem, and estimate they are currently losing about $4 million per year in lost bookings. Seven Mile Beach north of there is fine.
In addition to cigar smoking, my other hobby is diving. A lot of divers I know stay at the Sunshine Suites. Their rates are very reasonable (for Cayman) and you can save some additional bucks by doing some of your own cooking. They are owned by the Westin and are located across the street from the Westin mid seven mile beach. The beach is nice there. You pay a small fee and can use all the beach facilities and pool at the Westin. And their restaurant, the Sunshine Grill, is a favorite, especially for breakfast. Also, the Westin has the Red Sail Watersports on the premises, where you can rent all kinds of water toys (paddleboards, kayaks, snorkel gear, etc.) . And if you get inspired to try diving they will do an hour pool session with you there and then take you out on a guided dive that leaves from the Westin beach. We walk up the Westin a couple of times a week to have a drink and snack at their beachfront bar.
Cigars: They are somewhat expensive here but of course you can purchase Cubans here. The two places I would recommend are Old Havana Cigars (downtown Georgetown), and Club Havana (they have two outlets - one is a fancy cigar bar/restaurant and the other is smaller and mostly a cigar shop and bar - go to the smaller on on west bay road in the West Shore Centre mall.) Club Havana has a roller on premises and their house cigar (made with Cuban tobacco) is excellent. I'n a Nicaraguan fan and bring my own from our home up north. Sitting on the beach at sunset smoking a cigar - it almost doesn't matter what you are smoking - it's going to be great.
Things to do: beach, beach and beach. And eat - almost every restaurant on the island is good. If you are into music at night, check out the Lodge at the Strand Mall on West Bay road. I occasionally sit in with the bands there. I would avoid Stingray city - unless you want to hold a stingray together with 500 of your closest friends all clammering for a ray to feed or hold. And I would avoid the turtle "center" (it used to be called the turtle farm, as they raise the turtles for meat, but they thought it would be better to rebrand it as a "center".) I'd rather swim with the turtles than eat them.
One very cool thing we take our visitors to is a bioluminescnce snorkel trip. You can snorkel at night in the middle of millions of microscopic luminescent dinoflagellates. Cayman is home to one of very few bioluminescent bays in the world, so worth doing.
Happy to answer any other questions.