We went back and forth on whether or not we should splurge on a private boat for the day and ultimately popped for it (thanks to a hotel guest who overheard us debating and interjected: “just work extra hard when you get home!”). It ended up being our favorite day in Italy. Worth every penny. Rocco, Captain of Kaipoe and Positano native, pulled up to our beach chairs at Hotel Santa Caterina and off we went. Our first stop was to the port of Capri where we wandered the streets and enjoyed Aperol Spritzes at J.K. Place Capri, a gorgeous hotel not to miss. Rocco then took us swimming to hidden grottos, opting to skip the touristy spots. Our favorite grotto opened into a glowing green pool and through another tiny swimming a hole, a private beach filled with sea glass. Absolutely incredible. We anchored outside of La Fontelina Beach Club where the dingy came and picked us up for our 1pm lunch reservations. The people watching and crisp white wine on the terrace was the epitome of la dolce vita.