Marvel at the stunning views of the Sea of Cortez or soak up the sun in an infinity edge pool. Designed for indoor-outdoor living, you are guaranteed a blissful vacation full of sun and fun. Enjoy luxury hospitality with a 7-night stay at one of five private residences at Auberge Private Residences at Esperanza. 

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While there's plenty to do above ground, Grand Cayman's real draw is underwater. Dive a mere 30 feet to explore pristine reefs, coral walls descending hundreds of feet, and shipwrecks teeming with pastel-colored fish. If you prefer snorkeling, there's Eden Rock, Devil's Grotto at Seven Mile Beach and the best spot on the island a short swim out from the beach in front of our Inspirato Residences. On land, you'll want to venture to the Cayman Turtle Farm, discover the unique flora and fauna in the Queen Elizabeth II Botanic Park, and spend a carefree afternoon at Rum Point.

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Villa Dante is a stunningly-restored Italian farmhouse surrounded by olive groves and vineyards near Greve in Chianti.

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The Sunset Family Pool Pass for Life is designed for one Glen Ellyn family (two adults and all dependent children) to enjoy. The lifetime family pool pass is only valid for the family who initially register for the pass; it cannot be transferred nor can it be handed down to the next generation or any generation after that. Dependent children are eligible to use the family pool pass until the age of 26.

Winner chooses a luxury 7-night vacation in a multi-million dollar Inspirato home. Choose from 2-, 3-, and 4-bedroom villa in Los Cabos (Auberge), The Hamptons, Newport Coast, Punta de Mita, Scottsdale, Riviera Maya (Banyan Tree Mayakoba), Tuscany, Costa Rica, Grand Caymen or London (Apartment at THE COMO).