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I've done all inclusive resorts at two different Sandals' in Jamaica, as well as three Royal Caribbean cruises throughout most of the Caribbean. All with large groups of at least 10 people, either with extended family, or for friends' weddings. Though neither type of vacation is ever my preference, all were unexpectedly enjoyable. The cruises were fun and full of great activities, to participate in at your leisure. You see and experience a lot based on the multiple destinations, but yes much more regimented (a dress code at some meals, inspected bags to ensure you only drink their liquor, strict time frames if you go explore when at shore, etc). Versus an all inclusive resort, where it's totally unregimented but you're limited to the available on-site activities, even though you can come and go as you please, to explore the locale. Though cruises have prepay all inclusive beverage and then liquor packages, resorts don't nickel and dime you for much if anything, they even give you actual aloe for skin care after being in the sun and accidently getting burnt.
My favorite Caribbean resort trip was to Belize, at an affordable non-inclusive resort. The beautiful property was part of the rest of the little island community off of the coast of Belize City and it had plenty of activities happening naturally but others you could pay for a-la-carte. We explored the town on our own for the most part, there was a festival for Ms. Belize (she was on our puddle hopper flight from the airport to the island) but we also took a snorkel tour to the Great Blue Hole and another to explore the Xunantunich & Cahal Pech Mayan ruins. The primary guides for both were Black and just by slipping them each $20 tips at the end, we were magically never charged by the resort their resort cost for the tours. The only negative was that the beaches there weren't manicured, like at a Sandals, though the pools (steps from the beach) at the resort were great. Comparatively, the overall experience felt more authentic, by simply being able to interact with actual locals who weren't being paid to be friendly, unlike on a cruises or at an all inclusive resort.
My Mom was in the Bahamas during the Hurricane this year, though they were all still stranded at the resort the island she was on didn't suffer catastrophe. She'd been before but was thoroughly impressed by this particular resort. That short flight and her winning something like $5K at the resort casino might have influenced why she enjoyed it so much, letting her ignore any shortcomings.
My step-sister now swears by Disney Cruises and keeps trying to bully me into going with them every year. I thought for her kids sake, but how her husband tells it, they'd probably go without their kids, based on adult activities compared to other cruise lines.
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