Rosewood Castiglion del Bosco Resort in Tuscany

In my trip research, every so often I come across a place that seems too good to be true. Yet, when I visit, it defies all expectations and I wonder what took me so long to make it happen. The Rosewood Castiglion del Bosco is one of those places for me. Our first trip took place in early January, and Ioved it so much that we returned in April. We returned in January 2024 and 2025, and it was even more amazing. Needless to say, this is one of my favorite Tuscany resorts and we’re booked in the spring already. This is more than a hotel, it’s fully-restored village nestled in the vineyards of Montalcino, with a small chapel, the remains of a medieval castle, an on-site winery, a beautiful spa, and so much more.

The first thing to know about Castiglion del Bosco is that it is a splurge. For a milestone birthday or anniversary, or perhaps a honeymoon in Tuscany, it may be a splurge worth making. (Only you know your travel budget and what’s worth it for you.) This Tuscan resort is pure luxury in every possible way, and that does come at a price. Don’t be afraid of the off-season and shoulder season rates though. We’ve enjoyed the Rosewood every time we’ve been there, regardless of season. It really is one of the best resorts in Tuscany for a reason.

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Booking the Rosewood Castiglion del Bosco

In most cases, I prefer to book Castiglion del Bosco with a luxury travel agent. (As a luxury travel advisor, I can help you with this!) The reasons are quite simple. A good travel agent will always get you the best available rate, including any promotions that Rosewood is running that you may not find. Sometimes that is 15-20% off during certain times of the year. Other times, it means getting one night free when staying three nights.

Second, when you book with a luxury travel agent, you get a few extra perks. Some of the perks offered by the Castiglion del Bosco are pretty valuable, especially when you consider how secluded this resort in Tuscany is from Montalcino. We love to check into the Rosewood and stay on property the entire time, and they make it incredibly easy to do so.

• Upgrade upon arrival based on availability
• Welcome Amenity
• €95 Spa credit, to be used during the stay
• Daily Breakfast for two
• Early check-in/Late check-out as available
• Access to sauna and steam bath, fitness center, kids club, and bocce and tennis courts
• Free wifi

Booking the Rosewood Montalcino Without a Travel Agent

If you have the Capital One Venture X card, you can book through their travel portal and use your $300 travel credit towards the room rate. It doesn’t come with the extra benefits listed above, but it can be a great way to try this property.

The Rosewood Castiglion del Bosco is also part of AmEx Fine Hotels and Resorts, which would allow you to use your travel credit and get some of the bonuses above, but I’ve generally found better rates by booking directly with a travel agent. That said, you could use your $200 AmEx credit towards it!

Regardless of how you book, the service is always exceptional, and you can tell that the Castiglion del Bosco staff puts their guests first. Our experiences at this property, encompassing everything from service to local experiences, have made me want to book other Rosewood hotels. The Hotel de Crillon in Paris is high on my list!

Planning Your Tuscan Escape

Prior to arrival, the Rosewood concierge team will send you a brochure with all the experiences you can book during your stay at the resort. For foodies, they offer multiple cooking classes, a variety of wine tastings, truffle-hunting, and visits to local producers. (You can even experience the grape harvest if you visit in September!) For those who want to leave the resort, they can set up guided tours of Siena, Florence, San Gimignano, and more. They are also happy to help arrange spa reservations in advance, which I absolutely recommend.

There really is something for everyone at the Rosewood. Even if you don’t book official activities, you won’t be bored. We love taking long walks through the property and enjoy lazy afternoons on our terrace or at the pool.

How to Get to Rosewood Castiglion del Bosco

Simply put, you need a car. (You need a car to access most Montalcino resorts.) The Rosewood Tuscany is off the beaten path and about 20 minutes from the town of Montalcino. It is impossible to reach via public transportation. We’ve driven from the St. Regis Florence several times. On each trip, we’ve left around noon. It takes about two hours and was a pretty easy drive.

When we checked out of the Rosewood, we headed to Umbria for a few days at Roccafiore wine resort, which took about 2.5 hours. If you have the time in your itinerary, I definitely recommend pairing Umbria and Tuscany. The food and wine in both regions are amazing. I love the Borgo dei Conti resort in Umbria, and it would pair beautifully with the Rosewood for two different experiences in Italy.

On our second trip to the Rosewood, we drove in from another Tuscany resort, Borgo Pignano near Volterra. That drive was a bit shorter, but it was on smaller roads. I tend to get a bit of motion sickness, so we had to go a little slower.

After the Rosewood, we headed to Florence for Easter. I was glad that we spent a few days enjoying the peaceful vibes of the Rosewood before heading into the holiday weekend in Florence.

You can certainly hire a private driver to transport you to the Rosewood, but a car gives you the greatest flexibility to enjoy the scenic drives through Val d’Orcia.

Indulge in the Luxury Suites at Castiglion del Bosco

Because we don’t need a villa for two of us, I’m happy to book a standard room at the Castiglion del Bosco. The “standard” rooms are anything but standard. They are suites, impeccably designed with beautiful fabrics, stunning antiques, and a commitment maintaining the regional architecture. They are equipped with every modern luxury and the latest technology and still manage to feel like the best respite from a frantic world.

It’s difficult to put into words, but everything about the suites at Castiglion del Bosco inspires relaxation for me. When we arrived in January 2024, it immediately felt like we were home.

Junior Suite – Poggio alla Pigna

Each of the suites has its own name, which is identified on your key. Our first suite experience was Poggio alla Pigna (hill of the pine cone?), and it was incredibly romantic and cozy. This room is perfect for your Tuscany honeymoon. Our trip was in January, the weather was overcast and moody, and when they did daily turndown service, they lit candles and left us a bottle of their Castiglion del Bosco Rosso di Montalcino. It felt like a fairy tale – unreal and straight up magical. Our junior suite had a small table in the corner. We also had a small terrace with lounge chairs and a small table.

The bed was SO comfortable. (It’s tough to choose my favorite hotel bed – this bed, the Four Seasons bed, or the St Regis bed. The bed at CdB Tuscany is DEFINITELY a contender though!) What really stands out about it is the weighted duvet cover. I can’t remember the last time I slept this good, but the bedding was a large part of it.

The bathroom had a walk in shower and a separate soaking tub. I love the unique Harlequin tile, even though I would never do that at home. It fit a luxurious Tuscan aesthetic. The bath amenities were originally Ferragamo’s Bianco di Carrara, which I fell in love with after staying at the Lungarno hotels in Florence. (The Ferragamo family invested in and developed a number of fabulous hotels in Italy. If it’s a Ferragamo, I’m probably going to love it.) Now, they use Angeli di Firenze from the famous Santa Maria Novella pharmacy in Florence. The scent is divine, and I love the bath salts. The bathroom included every amenity you could possibly need. Loofahs, toothbrushes, lip balm, shaving kit… Everything was in its place.

By any standards, a junior suite at the Castiglion del Bosco is incredible. As a “base room”, it was truly beyond my imagination. If you can’t be happy in this room, you won’t be happy anywhere.

Borgo Suite – Sassi Bianchi

Imagine our surprise when we were escorted to Sassi Bianchi on our second stay. Sassi Bianchi is a corner terrace suite, and it was bigger than our first apartment. This suite is UNREAL. It has a living room, a huge bedroom, a walk in closet, and a huge terrace. If Poggio alle Pigna was moody, romantic, and perfect for winter, Sassi Bianchi was bright, airy, and perfect for spring.

The living room was so comfortable. The sitting area was the perfect place to curl up with glass of wine, and just like the junior suite, there was a small table in the corner. The windows opened up to a gorgeous view and there were French doors leading out to the terrace. There was a half bathroom in the living room, which wasn’t necessary for the two of us, but it was a nice luxury.

The bedroom was HUGE. I loved the bright colors of the pillows and the four-poster bed. There were two chaise lounges in the bedroom that I loved. Every detail was perfect, and the room had such a fun vibe. The walk-in closet was absolutely amazing, and I loved the full-length mirror. It was the perfect dressing area.

Like the junior suite, the suite bathroom had a large walk-in shower and a separate soaker tub. I loved how bright it was and how much light was in the bathroom. It had the standard Ferragamo amenities, but it also had bath salts, and I LOVED those. The ultimate relaxation experience.

Hands down, the best part of this suite was the huge covered terrace with lounge chairs overlooking the Tuscan countryside. I spent every afternoon out here – under the Tuscan sun – working, reading, and resting. We would open a bottle of wine and just be present in that place and moment. (The Rosewood hashtag on instagram is a sense of place, and this is exactly that.)

Terrace Suite – Suite della Pieve

We were upgraded to a terrace suite on our third stay. Suite della Pieve is a corner suite that feels so home-y. I immediately settled in, and given the challenges I was facing at work in the beginning of 2024, I can’t imagine being anywhere more comfortable. As we like to say, when we close our laptops for the day, we’re still in a vineyard.

Suite della Pieve has a nice sitting area and all the windows overlook the beautiful hills of Montalcino. The large living room is filled with overstuffed chairs, cozy throws, and beautiful views. There were small tables in the living room and the bedroom, so both Tom and I had room to work.

The canopy bed in the bedroom felt romantic and cozy. And, the bed was just as comfortable as I remembered it. We had a large walk-in closet with plenty of space. The room could be closed off from the living room easily, which made it possible for both of us to take calls at the same time.

Suite della Pieve has the bathroom that dreams are made of. With windows that open, the bathtub overlooks the countryside. I enjoyed watching the skies fade from sunset to blue hour to night while soaking in the tub. The separate walk-in shower is great with wonderful water pressure and plenty of hot water.

While I would enjoy seeing more of the resort, I wouldn’t be sad if this became “our” room”. When I texted a photo of it to a friend, she immediately texted me back and suggested I have a designer recreate the space in our home. It was that cozy and comfortable.

Savor the Flavors of Tuscany

One of the things I love most about the Rosewood is the commitment to local products and ingredients. The menus at the Ristorante Campo del Drago and Osteria Canonica change with the seasons and focus on Tuscan specialties. We have never had a bad meal here. Even when we’ve stayed at other wine resorts in Montalcino, we’ve made the trip to Castiglion del Bosco for dinner. It never disappoints.

On our first stay, our arrival gift included a box of fresh fruit, a home-made sweet treat and a bottle of the estate’s Rosso di Montalcino. This red wine is less tannic than the Brunello di Montalcino and can be a great souvenir from Tuscany because of its fair price point.

On our third trip, our arrival gift included fruit, a delicious pastry, and a bottle of Tom’s favorite vintage of the 2015 Castiglion del Bosco Brunello di Montalcino. This “small” touch was a huge gesture to him. We’re still not entirely sure how it happened, but it speaks to luxury resort experience and the things they do to make you feel welcome.

Brunello di Montalcino Wine Tasting at Cantina Castiglion del Bosco

We’re a little spoiled. Our first Brunello wine tasting in Italy was at the Castiglion del Bosco winery. That means Castiglion del Bosco was our first Brunello, and it was probably the first release of the 2016 vintage, which was a 5 star vintage year. We’re now Brunello wine club members at Castiglion del Bosco (with quite a Brunello collection).

We try to book at least two different wine tastings every time we visit. Even when we aren’t staying at the resort, we try to schedule a tasting. The guides really are so lovely and the vintages change. We have learned so much about wine production in Tuscany from their team.

We were truly fortunate to be able to try the 2015 and 2016 Brunello vintages on our first trip to the winery. Those vintages are considered to be some of the best in recent memory, and shortly after we tried them, they became impossible to find the US. When we visited in January 2024, we were able to try the much hyped 2019 Brunello, and we’re excited to see how it continues to evolve.

The wine tasting includes a visit to the production facility, the most gorgeous wine cellar in the world, and if you’re lucky, a trip to the vineyards. In the spring, we were able to visit the vineyard that is used for the Campo del Drago Brunello di Montalcino, which was gorgeous. I don’t consider myself a wine snob or even a sophisticated wine drinker, but I have a discerning palate for red wine. We REALLY love the Castiglion del Bosco wines. I do wonder if I have a greater affinity for the wines of the places we’ve visited merely because of the positive connections of those moments in my mind, but when we’ve shared these wines with others, they’ve really enjoyed them as well.

We returned to the winery as part of our 10th anniversary trip to Tuscany, and we celebrated with a Brunello vertical tasting and joining their Brunello wine club. We’re looking forward to returning in a few months. We took my mom and my sister to the Castiglion del Bosco wine lounge in Florence in November, and Gian Mario provided an equally lovely tasting experience for us.

Another Montalcino winery I recommend visiting is Tenuta Buon Tempo. It’s about 30 minutes away from the Rosewood Castiglion del Bosco hotel. We had their Brunello at Le George at the Four Seasons Paris, and their wines are absolutely lovely.

Fresh Pasta Cooking Class in Tuscany

The cooking school is located within Osteria La Canonica, which is incredible. You get to cook in the luxurious open kitchen on the second floor of the osteria! The classes are taught by the restaurant’s chef and include a visit to the kitchen garden. We literally picked fresh vegetables and herbs for our pasta dishes at the start of the day.

Our pasta class was a private experience, and we learned to make tagliatelle and chitarra pastas, as well as a filled tortelli. We made a sweet and savory meat sauce for the tagliatelle and a butter sage sauce for the tortelli. For dessert, we made a tiramisu. Once we were done cooking, we were served our own creations in subsequent courses (with Castiglion del Bosco wine!) at a table at La Canonica. It was a truly leisurely and luxurious experience. My favorite course was the tortelli. The portions are large and you won’t need after this class.

I’m really excited to take the Flavors of Tuscany cooking class or go truffle hunting on our next trip.

Osteria La Canonica

We were originally dubious about dining on-property at the Rosewood, not because we were worried about the quality, but because we were worried about missing out on some great local restaurants near Montalcino. (Caffe Sant’Angelo is still one of my favorite random restaurants we popped into on a cold winter afternoon in 2019!) However, one of the things we love about staying at the Rosewood is that you don’t HAVE to leave the resort (and we don’t!).

La Canonica is the more casual resort restaurant, and it is open for lunch and dinner. It focuses on local ingredients and the menu changes with the season. It’s classic Tuscan fare, and if it is your first time in Tuscany, I recommend trying the pappa al pomodoro and the wild boar tagliatelle as primi courses. Pici all’aglione is also one of my favorite pastas in Tuscany. The bistecca Fiorentina here is incredible. Let them cook it the way Italians eat it. It’s just perfection. (They also have great pizza if you’re wanting a light and easy meal.)

The waitstaff is incredibly kind, and they are happy to make recommendations for wine that will complement with your meal. We have started ordering some of the older vintages when we are staying at the resort. There’s just something extra delicious about having the wine in its place.

Campo del Drago is only open for dinner on Tuesday-Saturday. It’s a two Michelin starred restaurant with a couple of tasting menus, as well as a la carte dining. The menu is creative and modern with a focus on seasonal and local products.

Focus on Health and Wellness

Fitness, Swimming and Golf

In addition to the fitness center, the Rosewood offers yoga and pilates classes, bike rentals and tours, and hiking activities to keep you active and enjoying the beauty of Tuscany. We really love hiking through the property and winding our way through the vineyards. There is even a medieval church on-site that has been beautifully restored. Castiglion del Bosco translates to small castle in the forest, and it’s easy to explore both the forest and the vineyards on foot.

In the middle of the property, there is an infinity pool that overlooks the Val d’Orcia. The swimming pool is heated and enclosed in winter, so you don’t have to wait until summer to enjoy it. (In the warmer months, there is a pool bar available.) In the winter, there is a small Christmas market in the village and they open an ice rink near the pool. How cool is that?!

We aren’t golfers (especially not on vacation), but the private golf club at Castiglion del Bosco has to be one of the most beautiful golf courses in the world. (Okay, maybe the Ritz Carlton Half Moon Bay course is equally as beautiful.)

The Spa at the Rosewood Castiglion del Bosco

The spa at the Rosewood is very intimate and provides a serene experience for its guests. Its extensive spa treatment menu focuses on the natural products of Tuscany and their healing properties. (Think lavender, olive oil, and wine.) I took advantage of the Lost Remedies and booked a Tuscan Herbal Ritual. My therapist was incredibly talented, and she was quite concerned with the amount of stress my body was carrying. I felt so relaxed afterwards.

One of my most favorite spa treatments at Castiglion del Bosco has been the Santa Maria Novella Pharmacy facial, from the famous Florence pharmacy founded in 1221. I found it to be deeply hydrating and relaxing. Leti did an amazing job! If you are a facial person, I strongly recommend booking the Santa Maria Novella facial! (They also have a lot of the perfumes available to try, which is a good way to find your signature scent. I personally love the Acqua, Iris, and Angeli di Firenze scents!

Further, the spa includes a nice sauna and steam room, which are available by reservation, which ensures a private and relaxing experience. In the spring and summer, you can enjoy the serenity of the spa pool and garden. Tom and I both really enjoyed the spa, and I’m excited to go back and dive further into their treatment menu.