Discover What It's Like to Stay at the Best Hotel in the World: An Italian Resort

Discover What It's Like to Stay at the Best Hotel in the World: An Italian Resort
Courtesy of Rosewood Hotels 

An insider's view of the Rosewood Castiglion del Bosco hotel, a Rich Report reader's favorite.

A world-class hotel carries with it a baggage of high expectations when you enter its doors.

Upon turning our car off the main paved highway and onto the 5,000-acre resort's groomed gravel road, we began our adventure. In order to reach the hotel reception, we had to climb through the bosco — or woodlands — on either side of the undulating greens of Italy's only private golf course. 

On the hilltop, literally just a few kilometers from the villa, we could see a stone borgo surrounded by tall, skinny cypress trees - almost obligatory landmarks in Tuscany. We were swept off our feet right away, and within seconds, our luggage and bags were gone. 

Courtesy of Rosewood Hotels 

Since 2015, Castiglion del Bosco has flown the Rosewood flag after being opened by the Ferragamo family in 2010. As one of the early entries into Italy's booming borgo hotels, abandoned medieval hamlets have been transformed into upscale accommodations spread across multiple buildings and acres of land. 

In a comfortable environment, guests can experience a complete encounter with rural Italy through a curated version that includes accommodation and dining in historic buildings, cultural enrichment, and culinary experiences.

Courtesy of Rosewood Hotels 

The borgo at Castiglion is made up of a cluster of restored farmhouses that date back to the 17th and 18th centuries, near the ruins of a small castle dating back to the 1100s. A still-consecrated 14th-century church nestled in the compound consists of frescoes by the Lorenzetti brothers, two of the most important medieval Italian artists. 

Several vantage points throughout the resort reveal the resplendent Val d'Orcia, including restaurant patios, terraced gardens, and heated saltwater pool. For its preservation of Renaissance rural landscapes and utopian aesthetics of pristine, yet altered natural surroundings, the valley panorama is recognized as a UNESCO World Heritage Site. There are rolling agricultural fields, wooded stands, roads lined with cypress trees, and walled cities like Montalcino and Pienza nearby that are pristinely kept. 

Courtesy of Rosewood Hotels 

In this coveted position, Castiglion del Bosco delivers the full Tuscan dream, which has left my spouse and me, who have travelled extensively throughout Tuscany, often exclaiming "impeccable."

A bar, fireplace, library, and dining table set with welcome goodies certainly encouraged us to stay a while in the borgo suite at Castiglion. 

Our daughter watched the activity of the borgo from the window of the bathtub while enjoying Ferragamo bath amenities. The suite also had a separate bedroom, a walk-through wardrobe, and a huge marble bathroom. I had a date to keep — for a red grape-infused massage at the spa — after my daughter and I had indulged in afternoon tea and snacks at the borgo bar every day.


Courtesy of Rosewood Hotels 

While my daughter and husband explored the grounds, I padded down a landscaped path to the resort's small spa, which includes three individual treatment rooms and two couple rooms. As a result of local grape seed oil and lavender aromatherapy, my head-to-toe massage lasted a full 60 minutes, which was especially indulgent compared to typical 50-minute massages.

A dry sauna, hammam, relaxation area, and refreshments were all mys to use in the private wellness lounge, which I had all to myself after the massage. Although it is necessary to reserve the space in advance, this latter service is available free of charge to all resort guests. 

In the evening, I found my family playing bocce on the bocce court. We then headed to the bar for live music and pre-dinner cocktails (including kids' versions). There are two restaurants on-property (three when the golf club dining room is open), but Campo del Drago earned its first Michelin star recently. 

Temperini, the chef of the kitchen, draws upon the riches of his hometown of Siena to prepare dishes that are both comfortable and challenging. This beef stew-filled tortelli, topped with black truffle and panforte (a typical spiced cake of Siena), might not be your nonna's tortellini, but she'd approve of it. 

It was also a treat to eat the roast pigeon served with root vegetables from the resort's organic garden — an unusual dish for U.S. palates but a staple of many Italian country kitchens. My husband enjoyed a trademark truffle dish — a generous shaving of the fungus over two poached eggs — while we were there in white truffle season. He still talks about it today.  

From breakfast, we headed directly to a wine tour and tasting—because when in Tuscany, right? Campo del Drago offers a generous breakfast buffet with made-to-order items like eggs Benedict and pancakes. 

As part of the Brunello di Montalcino wine consortium, the Castiglion del Bosco winery was also founded by the Ferragamos. Brunello, now one of Italy's most expensive wines, was a founding member.

After a quick tour of the maceration area and barrel-filled cantinas, we visited the most impressive room at the winery - the rotunda-shaped sanctuary where the Millecento Wine Club members keep their private collections in individually labeled lockers and “visit” their wine periodically. We spotted Justin and Jessica Timberlake's names among the rows of lockers, as well as several Ferragamos. Naturally, a Brunello tasting followed.

Courtesy of Rosewood Hotels 

At Castiglion del Bosco, no hair is out of place. It's perfectly coiffed without ever feeling over-made-up. It's like one of those effortlessly dressed and accessorized Italian women who make it look effortless. Castiglion is definitely not effortless — it's clear there's a huge team working behind and in front of the scenes to ensure that every gravel path is raked, every pillow fluffed, and every crumb combed away — but its attention to detail, combined with a sense of place, sets it apart from its many competitors in the borgo hotel category. 

In the midst of winter, I asked my husband to think about how the Val d’Orcia resort and the surrounding countryside embody Tuscan ideals and, in general, Italian ideals as we drove home. As expected, he rattled off a list of Umbria’s attributes. "But that was perfect." he admitted.

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