30 Via Cristoforo Colombo, Positano
When it comes to romance, you can’t do much better than pastel-hued Positano, and Le Sirenuse—one of its most historic (since opening in 1951, it famously hosted John Steinbeck and many other notables) and glamorous hotels—takes full advantage of the storybook setting. Each of the beautifully appointed guestrooms boasts killer views of either the sea or the lush courtyards and is designed to keep the hustle and bustle of the pool and on-site restaurants (get to know the Mediterranean-flavored menu at Michelin-star La Sponda) and bars at bay. Once you’re done wandering the picturesque streets and soaking up the sun on the pebbled beaches, book a day trip to nearby Naples, Capri, Pompei, and Sorrento, or, explore by sea via the Saint’Antonio—the hotel’s vintage wooden fishing boat.
30 Via Arienzo, Positano
Off the beaten path and dripping in old-world romance, TreVille looks like it's carved into the side of a cliff hovering above the picture-perfect waters of Positano. The resort's 15 suites are scattered over four villas and are named after famous operas, ballet dancers, actors, and writers as homages to its previous owner, Italian director Franco Zeffirelli. While the property was thoroughly modernized by the Friedland family to include plunge pools, a tricked-out gym, and Sonos sound systems, for the most part, legendary designer Renzo Mongiardino's handiwork—colorful mosaics, hidden gardens—was left untouched. La Pergola, the on-site restaurant, happens to be excellent, so you don't ever have to leave (not that you'd want to).