Best Hotels

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.

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.

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.