Until Madeira Airport opened in the 1960s, the island could only be accessed by sea — and would you believe me if I said guests of this clifftop haven were carried up the craggy rocks in hammocks?  Nowadays, this intimate island off the west coast of Portugal offers plenty of modern comforts — but if you'd like, you can still arrange a traditional wicker sled ride down the mountain into the capital... and while you're there, perhaps taste fruits you've never heard of at the tropical Art Deco Food Market.  Seeking a lower-key activity?  Sip Madeira's world-class wine while admiring the striking scenery from Reid's Palace.
 
Private Perks: $100 resort credit, complimentary daily breakfast, early check-in/late check-out, complimentary upgrade, and more.