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An all-inclusive catamaran vacation - a timeshare on a catamaran! We spent most our time (a week) on a 10-person Tradewinds catamaran which was absolutely the highlight of our trip (thanks Donald & Audrey!
Gorgeous little cove beaches at the bottom of the cliffs Check out Danny's Beach Bar. Danny rents beach chairs and sells beer and rum punch from the back of his truck - he claims it's the "best rum punch on the island" and I'd definitely rate it in the top 3 (note that clothing is optional on Cupecoy, and when we were there, most opted not, especially the men).
Some of our favorite food was at the Lolos at Grand Case - amazing fresh grilled food, for super reasonable prices. At Talk of the Town, we had ribs for $4, snapper for $8 and creole shrimp for $6, and each came w/ a side. The coleslaw and curry rice and beans were wonderful.
Cool beach bar, lounge chairs on the sand, best rum punch on the island for just $3 all the time -- always freshly made - Wanda's own recipe, never pre-made mixes), and great fresh food - the blackend mahi mahi Caesar salad was amazing (just $14).
Pretty cool to watch the planes take off and land right over head, plus their fried shrimp are good, and pizza was wonderful - woodfire oven style, w/ great crust, sauce, cheese, etc., just $11-15 each
If you get the chance, take a ferry/sail to St. Barts - what a cool, beautiful island, w/ quaint shops, restaurants, bars -- check out Le Select, which Jimmy Buffet dedicated "Cheeseburger in Paradise" to --you can see why the rich and famous love this island!