We had a lot of fun at Morritt's Tortuga Club in Grand Cayman. Lots of activities onsite. Several different dining options onsite. Lots of things to do around the island. The water does have some sea grass and rocky bits, so that might not appeal, but we all loved it.

The White Sand slip-n-slide snorkel tour was a hit with our kids, and it leaves just a short walk away from Morritt's: https://www.whitesandwatersports.com/tours/double-water-slide-pontoon-boat

We also had a great time (from teens to 74 year old grandfather) with the Jet Ski tour through Fat Fish. They will provide transportation, if need be: https://fatfishadventures.com/jet-ski-safari/
But this would not be good for little kids... so you might have to pick a more traditional tour if everyone wants to go to sting ray city.

Check out the Marriott Vacation club on St Kitts

Half Moon in Montego Bay- they have rooms OR villas with 5-6 bedrooms that you can rent.. Its quite lovely and where Old Hollywood used to go. Good food, lots of activities but not crazy busy like a Beaches type resort.

Planning next year's (2026) February break week in the Caribbean that involves 3 generations, ages 4 - 75. We've been to Puerto Rico (Copamarina) and St. Martin (Grand Case) before with this group and have learned a bit about what works best: resort with pool and calm beach nearby so we can go back and forth between the two easily; restaurant(s) on site but not AI; apartment-style lodging options (1 or 2 bedrooms units for the families with kids); some watersports -- kayak, stand up paddle, snorkeling, etc. We prefer slightly smaller independent hotels over a giant Marriott or whatever, but aren't that picky. Just not looking for a huge Atlantis type venue that I know a lot of families head to for these types of trips. A huge pet peeve of mine is having to fight to get a beach chair before breakfast, and smaller hotels seem better about avoiding this.

Looking for non-stop flights from NYC, safe island where we don't feel like we can't leave the hotel (even though, realistically, we'll spend most of our time there), budget <$1K per night for a 1br unit.

Thanks in advance for any ideas!