World’s Best Golf Trips – Italy’s “New” Luxury Golf Resort Is Stunning

I’ve been to resorts where I wished I could stay longer, and I’ve been to resorts where I couldn’t wait to return, but it’s rare that I visited a resort I never wanted to leave. That was the case with the Rosewood Castiglion del Bosco in Tuscany, which is an Italian fantasy in the very best sense.

Just to clear up semantics, neither the hotel nor its golf course is new, per se. But even though they were developed by the same owner – Massimo Ferragamo, chairman of Ferragamo USA and son of famous fashion designer Salvatore Ferragamo – they were always separate entities. The golf club had the distinction of being the only truly private club in the country, at least in the American sense (there are lots of private clubs in the UK that allow outside guests to play, and since this is the birthplace of golf, and of golf clubs, that’s actually the more accurate model, one that got derailed and elitist when it reached out shores).

What that meant is that until very recently, you could stay at Castiglion del Bosco and have a great time – this is virtually guaranteed given the wonder of the place – but you couldn’t tee it up. I have a friend who is very well traveled, vacations in top luxury style and is an avid golfer. He visited a couple of years ago and told me that the resort is among his all-time favorites anywhere on earth. His only regret was that he couldn’t play golf.

But if he goes back this year, he can. The Rosewood and the golf club changed their policies halfway through 2022, and hotel guests now have access. In the US, when venerable Firestone Country Club in Ohio, a private club and 3-time Major Championship venue, decided in 2020 to open its golf course cottages (previously reserved for out of town members and their guests) to the general public on a limited “stay and play” basis (Read more here), it was enough of a loophole for Golf Magazine to move its Championship layout onto the all-important Top 100 You Can Play list, consisting only of public access venues.

In the same vein, while the number of rounds you can play on your visit (up to four) and times of day (actually preferable for most resort guests) are limited, and the club wants to maintain its reputation as elite and private, this has in effect created a truly exceptional all-new golf resort – in a country whose golf reputation is rising fast, with the Ryder Cup, one of the biggest international events in sports, coming to Rome this fall. For Italy, the boom in golf tourism may be a case of gilding the lily, since it is already the single most desirable dream destination for Americans in pretty much every poll, every year. Ask someone where they would go if they could take one more great vacation, and there’s a good chance the answer will be Italy, and even in Italy, which is chock full of wonderful hotels and resorts, it would be hard to beat this one. There are also golf courses at top tier luxury resorts such as Villa d’Este and Rocco Forte’s Verdura, but Castiglion del Bosco is simply next level.

“I wish I was at Castiglion del Bosco right now!” says Chad Clark, one of the nation’s top luxury travel advisors and principal of Phoenix-based agency Chad Clark Travel Ventures. Clark arranges deluxe trips from safaris to skiing to private island stays for high-net worth clients and celebrities, but his personal passion is golf, and he has played all over the world. “The Rosewood is always a home run with our clients looking for the perfect vacation in Tuscany. Along with the hotel, the Villas are absolutely beautiful and offer an amazing combination of space and privacy.” Clark’s firm is a member of the prestigious Virtuoso travel consortium, as is the resort (and around 1,400 other top luxury hotels worldwide) meaning if you book through a travel agent/advisor at a Virtuoso member agency you get extra benefits like upgrades and freebies.

The world is a big place, but Castiglion del Bosco was ranked the Number One Hotel in the World for 2022 by Travel + Leisure magazine, which is a pretty huge accolade. While historically that distinction has often been flawed, questionable or outright ridiculous, in this case it makes viable sense. By any measure the property is exceptional and one of a kind. The romantic centerpiece is an entire 800-year-old village, or Borgo, which not that long ago was Italy’s version of a ghost town. It had fallen into massive disrepair when first glimpsed by Ferragamo and his wife Chiara, and they understandably fell in love with the place. A noted designer and model, she oversaw a very hands-on and an extremely extensive renovation that honored history while sparing no expense. Ancient buildings that once served different purposes in the village’s life, including horse stables, a wine storage cave, even the priest’s residence, have been converted into luxury suites (there are no “regular” rooms). The medieval church is tiny but functional, you can even get married in it. But the centerpiece of the Borgo is the resort’s namesake Castle, an evocative, Instagramable ruin in the center of “town.”

The resort features just 42 suites, each one of them unique and decorated by Chiara Ferragamo, and not surprisingly, well-equipped with opulent Ferragamo fabrics. Everything else is first class from furnishing to toiletries to stemware. The latter is vital because the resort also includes a highly-acclaimed world-class winery specializing in the local superstar, Brunello di Montalcino, one of the world’s greatest wines. The resort is hidden down an unpaved road outside the charming town of Montalcino, which sits on a hilltop and can be seen from throughout the vast property, a popular day trip.

The suites are all in the Borgo, so you have the feeling of having your own private charming medieval Italian town. The village includes two excellent restaurants, casual and fancy, a very large chef’s garden that provides much of the produce for them, so everything is fresh and seasonal in classic Italian style (even the wild boar, or cinghiale, a menu staple, is local ), the spa, main pool, bocce courts, fitness center, kids club, shops and even a full-blown cooking school. There is a very cool lobby bar in one of the old buildings, an al fresco bar at the main restaurant and a pool bar. All of this is laid out along the “Main Street” right by your suite.

But the Borgo is just the heart of the resort, which spans 5,000 acres and was assembled with some neighboring farms. These original stone medieval farmhouses have been turned into 11 villas, also in the rental pool, which Clark mentioned. Each is unique, opulent, also designed by Chiara, and extremely lavish. There are plenty of private villas at other resorts with full-sized pools and chef’s kitchens, but few with their own tennis courts as you’ll find here. If all the rooms and villas are full, the resort still has about 100 acres for each party.

In addition to the state-of-the-art fitness center, the estate is interlaced with hiking, walking and jogging paths, and this being Tuscany, one of the most popular cycling destinations on earth, there are loaner bikes as well as an extensive slate of guided tour options. In fact, if you can pull yourself away from the fantasy estate, there is an amazing list of off-site activities, from VIP winery visits to art tours to truffe hunting to attending the famous Palio horse race in nearby Siena (bought to the big screen in the opening action sequence of the Daniel Craig James Bond film Quantum of Solace). There’s a guided walking tour of the Val d’Orcia, a rich green valley between Sienna and Grosseto so beautiful and well preserved with medieval farmhouses that it is a UNESCO World Heritage Site. So many movies have been shot here (Gladiator, Made in Italy, Romeo and Juliet, etc.) that they also offer a movie tour of the region. There are horseback rides, night astronomy tours of the Tuscan skies, and guided hiking on one of Tuscany’s most famous trails. They even offer the opportunity to make your own shoes in an Italian footwear workshop, an option I have never seen at another hotel.

You can begin to understand why I was loathe to leave.

But you don’t have to leave the resort to have unique experiences like the daily cooking classes, culminating in your own three course meals. There are yoga and meditation classes, and you can even take a landscape painting class onsite. The estate also includes the winery, which is fabulous and offers several VIP tours and tasting experiences for guests, as well as vineyard picnics.

There’s so much at the Rosewood that I almost forgot about the golf course, the newest guest attraction. It is the only Tom Weiskopf design in Europe (he passed away last year), and Ferragamo chose him because he doesn’t do a lot of earth moving, and the owner wanted the course to fit the rolling lush Tuscan landscape. It does, and it is a joy to play, but a tear inducing joy if you chose the tips – it features the longest par-5 in Europe, which was just lengthened to 701-yards (someone else went for the record and they decided to retake it).

The course is very good but not quite great. What is great is the experience, which is as close as most of us will ever come to having our own golf course. There are less than 200 members, most of whom live abroad (many here in the US, and you might want to join too after visiting, and compared to home it’s actually a pretty good deal), so the club averages just 15 rounds a day . I saw one other group and they were joined by their dog, the ultimate golf luxury (the resort is dog friendly too!). On top of the low play and little wear and tear, it is easily the best maintained course in Italy, a county not famous for these kind of immaculate conditions (I have played the top courses around the nation and recently did a big Ryder cup magazine feature, so I have seen). There is also another great Italian restaurant at the clubhouse, just to mix things up. The course is being renovated to improve some drainage and irrigation and update the bunkers, all to be ready for this spring.

If you love golf, love Italy and/or love the world’s finest hotels and resorts, Castiglion del Bosco should be on your short list.