Truly legendary, having hosted the likes of Jackie Onassis, Il Pellicano boasts one of the most spectacular locations on the Mediterranean Sea. A few miles from the ancient and charming old fishing port of Porto Ercole on the Argentario Peninsula, it has the crystal-clear sea below and a Spanish fortress above. Its thirty-nine rooms are dispersed in various cottages and villas. There’s a heated saltwater pool carved from the rock, privacy, views, and absolute discretion. And sunrises to die for, storms even better. Perched in a cove with a private beach below, it was started as a love nest that expanded into an unforgettable hotel with one of Italy’s best restaurants—two Michelin stars—with dishes that astonish the eye and the palate. Splurge: you only live once.