Welcome to Who What Wear Travels, a series of curated guides to destinations the fashion set loves. Consider this your download on everything from the chicest stays to the most memorable meals to the perfect travel wardrobe, all vetted by stylish locals and well-traveled fashion folks.

As much reporting as I’ve done on all the under-the-radar destinations to explore in Italy and around Europe, nothing can ever truly compare to Rome. Between personal and work-related travel, I’ve had the pleasure of spending a lot of time in the Eternal City this past month, using it both as a launching pad for a trip to Sicily’s Aeolian Islands and a way to flank a long-weekend visit to the Tuscan coastal town of Porto Ercole.