Italy's Top Villas:
The Dreamiest Places to Stay from Countryside to Coast
Sometimes you want an ever-moving adventure, full of sights, action, trains, planes and automobiles. Other times, you just want to unpack once and settle in. That’s where our Italian Villas come in: make yourself at home in the place renowned for its permeating sense of hospitality, where you can really relax and savour every detail slowly and with pleasure. Set out to explore the hidden gems of the area on foot or on bike while having a home base where to recharge or turn off your phone and succumb completely to your own personal paradise.
After years of carefully combing Tuscany, Umbria and the Amalfi Coast, I’ve curated a collection of some of the very best private villas in Italy, in addition to luxury apartments for longer stays in cities such as Rome and Florence.
Here are some of my best-loved discoveries, perfect for milestone celebrations, group getaways and taking time to forge memorable connections with la famiglia.
Built in the 17thC for Pope Alexander VII, this dazzling property is the perfect venue for an over-the-top celebration. Villa Cetinale is rife with history and beauty, elegantly braced with enchanted gardens and romantic furnishings. The villa was the perfect locale for a trip I planned a few years ago, where three generations gathered to celebrate a milestone anniversary.
The kids loved running around the villa and extensive grounds to explore hidden staircases and secret gardens, while the adults enjoyed a week of hiking, biking, and exploring Siena and Florence while making the villa their base. Perfect for a trip back in time through Italy’s rich artistic heritage with all the comforts of a modern fairytale.
This beautifully restored Tuscan property, which blends rustic farmhouse warmth with luxurious living spaces, is the perfect home base for a group of friends who want to play hard. Amidst the rolling green countryside, Podere Paníco sits atop its own cypress-lined hill from where the views are unparalleled and access to wonderful biking is immediate, either along gravel backroads or quiet country lanes.
I had a fabulous group stay here some years ago, and we sojourned to nearby Montalcino to visit Francesco Illy’s Podere Le Ripi for an incredible private dinner in the vineyards. Perfectly poetic, with expansive views and plenty of space to make yourself at home.
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Villa Origo La Foce
The serene Val d’Orcia is my family’s favourite area for our vacations, and Villa Origo on the La Foce estate is no exception to the area’s embarrassment of riches and beauty. Though the estate lays claim to an impressive and extensive heritage, recent renovations have rendered Villa Origo even more inviting and comfortable, even for children!
Another plus is its proximity to storybook villages like Pienza and Monticchiello (great for walking excursions), and since the property doesn’t require a weeklong stay, it’s the perfect countryside counterpart to another destination like Florence or Rome. I’d be remiss not to mention the Villa’s internationally-acclaimed gardens, with romantic and cinematic atmospheres exclusively for your enjoyment when you rent the villa.
Castiglion del Bosco
Ferragamo’s Rosewood Castiglion del Bosco estate boasts an extensive series of comfortable luxury villas for a home-away-from-home experience no matter the size of your group. A little jewel in the collection is Villa Castello, a three-storey three-bedroom retreat built on the ruins of a medieval castle that’s just perfect for an intimate group of close friends or a small family. In addition to the private pool and gardens, guests can make use of the resort’s many services, whether at tee-time on the golf course, beneath Tuscan herbal treatments at the spa or alongside the chef in a cooking class.
Though the surrounding area and nearby Montalcino offer plenty of walking and wine experiences, I personally suggest striking out into the sprawling grounds of the resort and grabbing a bottle of home-grown red, so you can easily choose to come back to your own slice of paradise at day’s end.
It’s nearly impossible to find something wrong with the Reschio Estate. Each villa is more stunning than the next, and the estate’s vast Umbrian grounds offer an array of activities–from horseback riding to truffle hunting, cooking lessons to gravel biking–that you might never leave… though visits to nearby cities like Cortona and Perugia are worth the effort.
Each of Reschio’s properties is impeccable, but to highlight a few: I love the eat-in kitchen, massive outdoor fireplace and charming bunk-beds of Bell’Aria for a large group with kids, the cozy rooms and personal wine cellar of Piantaverna for an intimate off-season escape, and Barco’s proximity to the estate’s stables and tennis courts while offering placid gardens to come home to, for those who like to play hard and rest easy. Oh, and no matter where you turn, the majesty of the unspoilt landscape is overwhelming (in a good way).
The lovely Villa Ferida offers a real sense of home, perfect for a group of friends to get away and soak in the exclusive side of La Dolce Vita. Also located in Praiano for excellent access to all areas of the Amalfi Coast, the reserved villa features a private indoor spa as well as a secluded outdoor pool–but don’t worry, the beach is just a 10-minute walk from your front door.
I personally love to visit this area in early autumn when the crowds have cleared away and the locals are relaxed; in fact, I even went for a delightful swim myself in Praiano this past October. Villa Ferida offers all that accessibility in a jewel-box coastal home that’s marked by simple luxury.
I’ll just come out and say it: Villa Bideri has the biggest private pool that you’ll find on the Amalfi Coast. Strategically located in Praiano–an authentic, less touristy part of the Amalfi Coast–but with easy (water taxi) access to Positano or Amalfi, Villa Bideri’s bright sea-view rooms and wide whitewashed terraces will have you partying with Poseidon in no time. There’s lots of space for a big celebration, whether poolside or piled into private boats for long, sun-soaked days at sea tooling around the coast, or venturing to glamorous Capri. Just ask your skipper to set sail towards the freshest plate of spaghetti alle vongole.
Alternatively, I’ve had great success stoking the coals of the villa’s wood-burning pizza oven for a fun pizza night making the region’s most famous (and most favourite) meal.
Villa San Giacomo
The roomy and beautiful Villa San Giacomo’s idyllic location hovering over Positano is just one of the features that make this spot so memorable. This is a great choice for a big group of friends who are game for lots of fun experiences, as Positano’s chic cafés, restaurants and shops are just steps–or rather, staircases–away.
The excellent hiking trails which depart directly from the front door connect up through the impressive vertical coastline for one breathtaking view after the next, and can even connect to the famed Pathway of the Gods. If you want a break from sea kayaking to secret beaches and stuffing zucchini blossoms in a gourmet kitchen, the meandering gardens and sea-framing pergolas of the villa are the perfect places for an afternoon read or aperitivo.
If you’re seeking your very own mini-wellness resort, look no further than Villa Milù. Located close to the town of Amalfi, the villa’s endless terraces, impressive indoor spa and on-site lemon groves all contribute to a sense of comfortable contemporary sophistication. Milù is the perfect getaway for a group of friends, especially if you all love the purity of nature and the sea, as Amalfi’s history as a maritime republic still permeates today.
My love affair with the Amalfi Coast has gone on for decades now, and one of my favourite walks in the region begins with a guided stroll through town to relive its spirited history, then continuing up through fragrant groves of citrus blossoms through the Valle delle Ferriere. Accompanied by birdsong and the rustle of gentle waterfalls, it’s easy to lose a sense of time while passing ancient paper mills and glimpses of the far-off sea. Don’t worry, the infinite blue will be waiting for you at home come dinnertime.