Live Out Your Fairytale Fantasies at These 11 Italian Retreats

A medieval castle, a church, and a Borgo comprise this centuries-old Tuscan wine estate with storybook-worthy vistas. Now, the Rosewood Castiglion del Bosco, the 5,500-acre country resort has 23 suites and ten restored farmhouse villas, a cooking school, spa, infinity pool, and rolling fields of lavender.

Come to Hotelito Lupaia, a converted stone farmhouse dating back to the 1200s, for an enchanting hilltop setting overlooking Montepulciano’s lush hills and ancient villages. But stay for charm overload in one of seven unique rooms with exposed beams, hand-painted walls, antique furnishings, and restored fireplaces.

Live out your escapist fantasies at Sextantio le Grotte della Civita, where a cluster of 18 prehistoric limestone caves have been reimagined as posh, minimalist dwellings. Cobblestone floors, candlelit bedrooms, standalone bathtubs, and rock-chiseled terraces overlooking Matera’s hills and valleys make this an idyllic hideaway.

Towering atop a thousand-foot cliff, Hotel Caesar Augustus’s 55 rooms and infinity pool jut out over the glittering sea below delivering to-die-for panoramas of the Bay of Naples, the volcanic isle of Ischia, Sorrento, and Mount Vesuvius. Not to be missed, spectacular sunsets from the terrace bar.

Once the summer retreat of an aristocratic 19th century family, this Cinderella-esque lakeside manor is the stuff that dreams (and deep pockets) are made of. Ticking every fairytale wish, Grand Hotel Villa Feltrinelli has regal balconies, princess towers, thousands of Venetian antiques and frescoes, a 500-label wine cellar, and an eight-acre Italian garden overlooking the water.

From queens and empresses to Hollywood jetsetters, the well-heeled have been flocking to the historic sun-soaked shores of Villa D’ Este for centuries. Amid a glorious 25-acre Renaissance garden, 152 regal rooms feature antique furnishings, silk-brocade drapes, and swoon-worthy lake views. Don your swankiest shades and sip a Bellini beside the floating pool.

Entering Ca’ Sagredo is like stepping into an 18th-century Venetian masterpiece. Aside from gasp-inducing Grand Canal views, this landmarked 15th-century palazzo turned 42-room hideaway features golden chandeliers, paintings by Renaissance and Baroque masters, a glittering ballroom with frescoed ceilings, and marble baths.

Old world charm oozes from Castello di Petroia, a thousand-year-old castle set atop an Umbrian hillside. Stroll the ancient fortress’s winding stone paths and olive-tree shaded grounds surrounded by verdant valleys and misted landscapes. In the evening, complete the fantasy with a classic Umbrian menu in the stone walled castle restaurant, set romantically fireside.

At Grand Hotel Majestic Già Baglioni, marvel the city’s breathtaking terracotta roofs from the 109 achingly romantic suites replete with canopy beds, Murano-glass chandeliers and marble-laden bathrooms; meander the spaghetti maze of enchanting medieval streets; then dine on divine Bolognese cuisine beneath frescoed ceilings at I Carracci restaurant.

Perched high in the rocky hills of Taormina at the foot of the ancient Greek Theater, the Belmond Grand Hotel Timeo is an icon of storied nobility and Italian glamour. The refashioned 19th century residence has 70 Baroque-style rooms and 5-acres of terraced gardens backdropped by mindboggling views of Mt. Etna and the Sicilian coastline.

At the Four Seasons Florence, this restored 15th century palazzo hides a dazzling 11-acre garden that mesmerizes with blooming botanicals, ancient towering trees, and a 16th-century convent. The 116 Renaissance–inspired rooms are opulently decked with original Italian frescoes and hand-painted sculptures.