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Islands I've been to:
Hawaii: Maui, Big Island, Kauai, Molokai, Oahu
Caribbean: St. Thomas, St. Maarten, Puerto Rico, Cayman Islands
US: Kiawah Island
Europe: Sicily, Crete
Asia: Bali, Koh Samui, Koh Phangan, Phuket, Singapore (not for beaches)
By far, the nicest beaches I've seen are in the gulf of Thailand. Kauai is my favorite though for the hiking/scenery/landscape.
I'd go to Madagascar, Galapagos, Bora Bora, Canary Islands. Somewhere exotic and expensive if it's free.
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