• Villa Spalletti Trivelli (Rome): Recent upgrades have only enhanced the unique experience of staying in a neoclassical mansion in the middle of the capital. Opulence plus impeccable, understated service comes at a price, of course. When our lottery numbers come up, we will be booking a stay here—a long one. 

  • Santa Caterina (Amalfi): Set in fragrant citrus groves above the sea, Santa Caterina is not outrageously posh, just magically transporting. Ceramic tiles, a smattering of antiques, sea-view terraces, a garden path leading to a private beach—it’s all worth the splurge. Shoulder season rates and special offers help bring the cost out of the stratosphere. 

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  • Palazzo Tolomei (Florence): A palace where Raphael once stayed—perhaps even giving its owners a painting to pay his rent—sounds grand indeed, and you won’t be disappointed. The Renaissance layout and a baroque redecoration from the 1600s are intact. 

  • Frances’ Lodge Relais (Siena): This family olive estate is bound to be among your favorite spots under the Tuscan sun. Nestled on a hillside, it has many quiet corners, a pool in the garden, richly hued rooms, and suites accented with family pieces. The towers of Siena beckon in the near distance.

  • Fra I Sassi Residence (Matera): Staying in a cave is an experience in itself, especially when accommodations are as stylish and comfortable as these. All open onto a meandering, sunny terrace with a front-row seat on a sculptured cluster of cave dwellings that tumble down surrounding cliffs.

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  • Hotel Mediterraneo (Rome): Upscale Art Deco Hotel Mediterraneo is the flagship of a trio of hotels near Termini Station run by the Bettoja family. Others are even more budget-friendly, but all offer vintage charm, old-school comforts, and warm service from a loyal longtime staff. They don't make 'em like this anymore. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.