Montalcino Travel Guide

Despite the popularity of the Brunello di Montalcino wine, I don’t think people spend nearly enough time visiting Montalcino. This is evident by the fact the town shuts down in the evenings, particularly in off season. The more time we’ve spent in Montalcino, the more it has revealed itself to us. Because I’ve really struggled to find a lot of information beyond the many day trips to Montalcino from Florence or Rome, I decided to put together my own Montalcino travel guide. This allows me to collect all of my recommendations in one place. I will always come back and updated it after future visits.

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Getting to Montalcino

The most effective way to visit Montalcino is to rent a car. If you’re not willing to drive, you’re going to waste a lot of time on public transportation. For reference it takes almost 4 hours to get from Montalcino to Florence on public transportation. It’s less than 2 hours by car. Similarly, it takes 5.5 hours to get from Rome to Montalcino. Exploring Tuscany by public transportation requires buses and regional trains, rather than high-speed trains. I recommend picking up a copy of Road Trips Italy to learn a little bit more about Italian driving culture. If you do rent a car, we’ve had the best experiences with Hertz and Sixt. I would not rent with Europcar, even if they are cheaper.

If you absolutely do not want to drive in Italy, taking the train and spending a few nights in Siena might be a better bet. You can also take the train to Cortona or San Gimignano. All are just a little bit easier to get to than Montalcino, Pienza, or Montalcino.

We’ve had very positive experiences driving in Italy, and it’s definitely allowed us to have deeper cultural experiences because you’re not just in the places that are easy for tourists to get to. And, even in those touristy places, most day trippers are gone by the evening and you can have an even more memorable experience!

Choosing to Visit Montalcino

Our TuscanY Sightseeing Phase

I feel like we’ve gone through several phases on our Italian hill town journey. Our interest in Tuscany was piqued by an olive oil tasting in San Gimignano while driving from Cinque Terre to Montepulciano. On that trip, we drove through the Crete Senesi and became enamored with the beautiful landscapes around Siena.

We started diving into the heart of Tuscany by visiting Montepulciano in 2018, which felt accessible and was great for sightseeing. We stayed at the beautiful Palazzo Carletti in the heart of the medieval town and used our days to explore the town on foot. From top to bottom, we roamed the streets and popped into every church we could find. (I love the diversity of architecture styles in the churches in Montepulciano.) Once we felt like we saw Montepulciano, we used it as a base to explore Pienza and the rest of the Val d’Orcia by car. This continued for a few years, and we even took my mom to Montepulciano for a night. (We wanted her to experience a true bistecca Fiorentina at Osteria Acquacheta with Giulo!) Montepulciano was our phase of sightseeing in Tuscany.

Our Tuscan FOodie Phase

In 2021, we visited Cortona for the first time, and it quickly replaced Montepulciano on our Italian itineraries. Not only did I fall in love with staying at the Monastero di Cortona hotel (and spa!), but we started to truly appreciate Tuscan cuisine. There are so many outstanding restaurants in Cortona that it quickly became one of our favorite places to do long weekends in Tuscany. I would say that our visits to Cortona helped us better understand la dolce vita, where our biggest question was where we would have apertivo before dinner. We learned to (mostly) stay put, slow down, and enjoy our meals, so Cortona was definitely our Tuscany food phase. (The Cortona basilica is beautiful, too!)

Our Tuscan Wine Phase

Today, we’re in our Montalcino wine phase. As I write this, I’m particularly stuck how our journey through Tuscany over the years has shaped our travels in so many ways. The first time we visited Montalcino, we weren’t that excited about it. It didn’t have the big, beautiful piazzas that Italy is known for (but it did have some outstanding views). We weren’t really into the wine bar scene and figured it would be expensive. Montalcino didn’t show itself as easily as Montepulciano. And, I think that’s why we love it now.

We’ve met some of the kindest souls in Montalcino. It’s even slower than Cortona and forces us to completely stop moving in most cases. We enjoy the beauty of the views, the beauty of the wines, and the beauty of the Italian people who will open up and share their passion with you if they feel like you want to learn.

Wine Tasting in Montalcino

It’s important to know that, in 2025, Italy changed some of their laws related to drinking and driving. The punishments have become much more severe. (Drinking and driving is a really bad idea, and it’s an worse idea on small roads that wine through the hill of Tuscany. If you’re going to do it, you really should consider booking a wine tasting tour with a driver.) While it can be nice to visit wineries and enjoy tastings, you also can taste many wines without ever leaving Montalcino.

Enoteca la Fortezza di Montalcino Wine Tasting

On the edge of town, you’ll find the fortress of Montalcino. And, within the fortress, you’ll find Enoteca la Fortezza and Sergio. Sergio is a sommelier with a personality, and if you want to learn, appreciate, and enjoy wine, he’ll happily share his passion with you. This is one of the oldest wine bars in Montalcino, and it offers a wide variety of producers and price points.

The first time we met Sergio, we were on a specific wine mission. We knew we wanted a certain producers and were looking for older vintages. While he certainly found all of those for us, he also encouraged us to try a few producers we didn’t know. We didn’t know Sergio was a wine legend at the time, but we’ve since learned at our monthly wine dinners how many people love Sergio because of his passion for good wine, as well as his thoughtfulness.

Imagine our surprise when we turned a few months later, he remembered us and our wine preferences. He was happy to see if he could find additional bottles for us. And, again, he encouraged us to try some different wines that he really loved at the time. It wasn’t high pressure sales, but it was Sergio saying, “hey, I have this open and I enjoy it, and I think you might, too.”

Current Vintage Brunello Tasting

Most recently, we went back and asked him if we could do an official wine tasting with him. We started with a tasting of 5 current vintage Brunellos, which we quickly bumped up to 7 because the wines were so interesting. We started with the 2020 vintages and made our way to the 2019 riserva vintages. Sergio gave us a few details on each wine and left us to form our own assessments and rankings. While we were trying those wines, he brought over a glass from our favorite producer so we could see the differences. The more questions we asked, the more he wanted to share.

We left that afternoon with a whole new appreciation for a lot of producers we hadn’t had the opportunity to try and a promise to return the following day. We were able to try some of the superstar producers of Brunello di Montalcino, but we also tried fantastic wines from small producers that would never make their way into our wine world without Sergio.

Blind Brunello Tasting of Small Producers

The next afternoon, we arrived to the fortress to find that Sergio had orchestrated a blind tasting for us. We settled down with a variety of wines, all of which were super interesting and complex. Sergio gave us all the time we needed to taste the wine and brought out charcuterie and bruscetta to enjoy with it. When we had finalized our rankings, he showed us that they were all 2019 riservas at a variety of economical price points. They were exceptional PQR (price-to-quality ratio) wines. It was easy to see how much time and care he put into finding some truly special wines for us. And again, he pulled out a bottle that hadn’t yet been released for us to try because he thought it was really special and we would enjoy it.

Ultimately, we diversified our wine collection because of the care that Sergio has put into helping us understand how different wine can be. Sometimes we can be hyper focused on what we know and what we feel is the best buy economically. Sergio found ways for us to be more open to different wines because of his deep knowledge of producers at every price point. (Enoteca la Fortezza offers free shipping for orders of 12+ bottles, and we enjoyed getting to mix and match.)

Enoteca di Piazza Wine Tasting

One of the first places that we tried Brunello di Montalcino is Enoteca di Piazza. This wine shop has several locations throughout Montalcino. We like the one right off the “main square” on Piazza Giuseppe Garibaldi. If you have the opportunity to meet Alessandro, he has been super helpful for us. I think he’s the reason that Tom became super interested in old vintages, actually.

Alessandro was very helpful and kind to locate a variety of wines and vintages that we were looking for, and he also held on to it until it was a better time to ship. We ordered wine in April and he held on to it until November for us. While most wineries and wine shops will do this during the warmer months, we appreciated it nonetheless because it is a long time to have wine taking up space in your cellar.

Choose Your Own Glasses Wine Tasting

Enoteca di Piazza uses the wine machines that allow you to pour by the glass and choose your pour size. In that way, you can try as little or as much as you would like from a variety of producers. They offer a handful of tasting options, ranging from Brunello exclusive tastings to tastings of the popular Italian wines (including Amarone, Brunello, and Barolo). You can sip and shop or you can head to one of the tables outside or at the restaurant across the street.

Choose Your Own Bottle Wine tAsting

One of the most transformative moments in our wine experience was when we found a 2012 Campo del Drago at Enoteca di Piazza. We found out that they would open the bottle for us to enjoy at La Taverna di Baietto. We were able to order food and allow the wine to open up. (The truffle tagliere board paired perfectly with the older vintage!) We were so excited about it that we offered Alessandro and his colleagues to try the wine with us… and in turn, they shared some of their favorite wines with us. It was a beautifully human moment that really helped reaffirm that great wine is meant to be shared with folks that will enjoy it.

Visiting Wineries around Montalcino

To be completely honest, we started visiting Montalcino because of the wineries that we wanted to visit. (Well, to be honest, we started visiting because I wanted to stay at Castiglion del Bosco, but that’s it’s own discussion below.) However, we decided we needed to stay in Montalcino because there were some very specific wineries we wanted to visit. While there are many Brunello wines that are exported to the United States, you can find older vintages and a most robust collection of wines by visiting the winery.

We love meeting the winemakers and learning more about their processes, too. While we obviously have our favorites, here are a few wineries that we love around Montalcino. All of these wineries offer affordable and approachable visits. (I’ve definitely done a double take at the cost to visit some of the most famous producers. I’m not there yet, particularly because I can visit Sergio at La Fortezza.)

Best Brunello Wineries to Visit

• Castiglion del Bosco – We’re wine club members because my husband fell in love with the 2015 Brunello di Montalcino here. I won’t tell you how much of their wine is in our cellar, but even “bad” vintages are great here. They offer a variety of tastings including red wine and white wine tastings, as well as Brunello vertical tastings. (My mom isn’t a red wine person, but she really enjoyed the Chardonnay at CdB. We might have also started converting her to red wines.) The members wine cellar is one of the most beautiful tasting rooms we’ve ever seen. They also have a wine lounge in Florence if you want to book a tasting there. (We love Gianmario!!)
• Tenuta Buon Tempo – Our introduction to Buon Tempo was at Le George in Paris (one of my favorite restaurants in the world!). We loved it so much that we went and found Filippo on a November trip to Tuscany with my mom. Getting down to Buon Tempo was an entire experience, but it was fantastic. We have not found Buon Tempo in the United States, so we bring it back from Italy. It’s rare that we find it. However, Filippo’s sister owns Enoteca Bellini in Florence, and you can find and try Buon Tempo wines there. The Rosso di Montalcino is fantastic, but we really love their Brunello, too.
• Ciacci Piccolomini – This is probably Tom’s second favorite Brunello. We’ve visited this winery twice, and Shenelle has been the best guide on both trips. The first time we did a general overview of their wines (all reds), and the second time we visited, we did a vertical tasting of the Brunello di Montalcino. They make some interesting Super Tuscans, so if you aren’t a Brunello drinker, this might be your best bet in the Montalcino area.
• Mocali – We did a visit to Mocali on a terribly rain winter day in March. Alessandra made us feel so welcome and was happy to show us the cellar. The smell was unbelievable, and they have a small museum of ancient winemaking tools that you can view (not unlike the exhibition at the museum in Montefalco!) While this tasting was very simple, it felt very authentic and close to the ground.
• Altesino – We stayed at Altesino, and they included a tasting as part of our stay. They did a great job of explaining the relationship between Altesino and Caparzo and showing us the vineyards. We really enjoyed trying their wines, especially the Super Tuscan, which was definitely Tom’s favorites. Just an FYI – Altesino is far less expensive in Italy than it is in the United States. If you’re looking to buy some great Italian wine as souvenirs for friends or family, these are wines to pick up. They would also make great hostess gifts. (Our wine suitcase pays for itself over and over.)

Where to Eat when Visiting Montalcino

Montalcino is such an interesting place. If you ask people where to eat in Montalcino, chances are, they will give you a list of restaurants in the area, not the town. Don’t sleep on the recommendations that are outside Montalcino. We’ve had some amazing meals outside of the city center of Montalcino. Remember, we like to travel during off season, so it’s usually slower. Some restaurants have seasonal closures, so it’s always important to call in advance, make reservations, and have a back up plan.

Pizzeria San Giorgio – Montalcino

One of the things that can sometimes be hard to find in Tuscany is good pizza. I’ll admit – I was a little dubious when Tom suggested San Giorgio, but he was so excited about the wine list that I agreed to use one of our dinners for it. They have a great selection of wines by the glass, but they also have a lot of wines that you won’t necessarily find anywhere else.

This might be my favorite pinci all’aglione that I’ve ever had, especially outside of Cortona. Pinci all’aglione is a hand-rolled pasta with a garlic tomato sauce that is made with the large garlic bulbs that are specific to Tuscany. It’s succulent and flavorful when it’s done right, and this was no exception. Our pizza was cooked to perfection – with the perfect sauce, cheese, and topping ratios.

So, let’s talk about the wine. We had come in with a couple of very specific producers that we wanted to try. Many were sold out because that’s reality about the 2019 vintage. I don’t blame the restaurant. When we couldn’t come up with an alternative, the waiter took my husband to the wine cellar and they debated the pros and cons of each wine based on what we were ordering. He was fiercely honest about what he thought was too young and wouldn’t pair well. (Fantastic.) Once we settled on a bottle of rosso di Montalcino, he proceeded to bringing out serval additional glasses for us to try from 2013-2020. It was absurdly kind. We ended up buying a few bottles of the things he showed us, and when I did my research, most of them are bottles that are not readily available.

A little kindness goes a long way in opening the hearts of Italians, even in the heart on what many would deem to be a very touristy hill town in Italy.

Enoteca Grotta del Brunello – Montalcino

Grotta del Brunello is a wine bar in the center of Montalcino. It’s located in a wine cave (hence the name), and it has fantastic ambiance and a very kind staff. We decided to do dinner here one evening when wanted something easy. They make some of the most beautiful charcuterie boards in Montalcino, and everything was very tasty. We let our waiter recommend his favorite Brunello wines, and we ended up trying a small producer we didn’t know and one that Tom had been wanting to try.

It was quiet, cozy, romantic, and we would absolutely return. This is also a great place to buy some tasty souvenirs as they have a great selection of olive oils and other local products. Prices are very fair.

Enoteca Bacchus – Montalcino

On a cold, rainy night in November, we left Castelgiocondo in search of dinner with my mom. Bacchus was one of the only wine bars open, and we were venturing towards hangry status. I can’t imagine they were excited to see us, but they gave us a table and really went above and beyond to make us comfortable. They worked hard to find a white wine that my mom would enjoy, and Tom and I rotated through a couple of their red wines by the glass. The menu is simple – panini, basic pastas, and traditional Tuscan meat and cheese boards. Our pastas were served in wine bottles that had been recommissioned into serving dishes (very creative), and everything was made fresh. While I wouldn’t say the food was extraordinarily memorable, it was good. What stands out most was how patient and kind they were.

And, because of that, when we went back to Montalcino and wanted to buy wine for our dinners at our vacation rental, we bought from Bacchus… and they made such to send us home with a corkscrew, just in case. They are changing management, but I hope this spirit remains.

Trattoria Il Pozzo – Sant’Angelo in Colle

Every single person that we know in and around Montalcino recommended Il Pozzo to us. Honestly, I’m sad that it took us so long to get there because it was truly a lovely experience. This is a simple Tuscan trattoria with the one of the best bistecca Fiorentinas that I’ve ever had in Tuscany. It was truly cooked to perfection and beyond tender. Seriously – it was like cutting butter and the meat just melted in your mouth. We also really enjoyed our antipasti – we ordered Il Pozzo, which provided us with bruschetta, crostini, a variety of meats, and different aged pecorino cheeses. It was obvious that the pasta was made by hand, and the crostada for dessert almost stole the show.

But then we have to talk about the wine list. Il Pozzo has one of the best wine lists in Tuscany at very fair prices. It’s a mix of high quality wines and many lesser-known prodcuers. We ordered a 2015 Brunello from Sesti (one of my favorite hard-to-find Brunellos) for our bistecca, and the 2019 Piccolomini for our first courses. Neither disappointed, and we had a great conversation with the restauranteur about the wines. We loved being able to order older vintages with our dinner, a privilege generally reserved for our meals at home.

We will absolutely be back here.

Caffe Sant’Angelo – Sant’Angelo-Cinigiano

Located a stone’s throw from all the most famous wineries in Montalcino, Caffe Sant’Angelo is everything your looking for in an Italian restaurant. Skip the expensive tasting menus at the wineries nearby and come here. It has a short hand-written menu (exclusively in Italian) that changes with the day and the season. The menu is comprised of traditional Tuscan favorites, so it’s a great way to be introduced to the local cuisine. Prices are reasonable and everything is made Fresh. Take your Italian language skills and put them to work. Caffe Sant’Angelo is inexpensive, hearty and fresh.  I really enjoyed my handmade spicy tomato pasta with pecorino.

Vineria Aperta – Castelnuovo dell’Abate

The first time someone told me to go to beach club in Montalcino, I laughed. While the sea does impact parts of Montalcino’s vineyards, there isn’t a beach that close to Montalcino. Eventually I convinced Tom that we should have a late lunch at Vineria Aperta after visiting some of the wineries nearby. The vibe is laid back, casual, comfortable, and a bit tongue in cheek. We loved it.

They have a fantastic selection of wines by the glass, but they also have a wide variety of wines by the bottle to try. The Montalcino beach club offers a couple of wine tastings (book in advance, they aren’t always available on demand), if you would rather enjoy your tasting with a view and with food. If you are new to Brunello di Montalcino, they offer a tasting that includes the 4 different areas of Montalcino. There is a definite difference in the wines, so it’s a great way to figure out what you like. (If you tell me that you don’t like Brunello, I’ll always ask which ones you’ve tried.)

Osteria La Canonica – Castiglion del Bosco

The “casual” restaurant at the Rosewood Castiglion del Bosco property is the most upscale restaurant on this list, and even if you aren’t staying at the resort, it’s a great option for a truly special meal. What we like to do when we’re not staying on property is book lunch at La Canonica and follow up with a wine tasting at the Castiglion del Bosco winery. La Canonica is open for both lunch and dinner, and they have a light menu outside of their official seatings. It focuses on local, seasonal ingredients, and it’s not uncommon to see the chef heading out to the garden to get herbs and vegetables for the day’s meals. It’s classic Tuscan fare.

If it is your first time in Tuscany, I recommend trying the pappa al pomodoro or the wild boar tagliatelle. They also have a fantastic pici all’aglione. If it’s truffle season, try the truffle. It’s simple and they do a fantastic job of letting the flavors shine. (It’s a splurge worth making, I promise.) And, if the lasagnetta is on the menu, order it. Lasagnetta is a deconstructed lasagne, and my mouth is watering just writing about it. They also have a great pizza if you’re wanting something easy. The 2019 Castiglion del Bosco Brunello pairs perfectly with their diavola pizza.

If we’re talking about secondi piatti, the bistecca Fiorentina here is incredible. Let them cook it the way Italians eat it. It’s perfection. I would pair it with an older Brunello, and the sommeliers are great at making recommendations that make sense for your budget. They are incredibly kind. Their wine list also includes wines beyond CdB, but we love being able to their wines in the restaurants.

If you want an even more elevated experience Ristorante Campo del Drago is their two Michelin starred restaurant. It is only open for dinner on Tuesday-Saturday and offers a couple of tasting menus, as well as a la carte dining. It’s more creative than La Canonica.

Where to Stay in Montalcino

We’ve had a lot of different with accommodations around Montalcino. When we want a rural experience, we’ve stayed in easily accessible vineyards that are a short drive from the Montalcino city center. We’ve rented an apartment in the Montalcino city center. We’ve stayed at luxury wine resorts that you (I) don’t want to leave. And we’ve stayed at some wine resorts that are nearly impossible to get to if it’s rainy.

The great thing about Montalcino is that it’s widely accessible to almost any budget. While it’s true that you get what you pay for, it’s also possible to have a good stay on a budget. When choosing accommodation in Montalcino, you need to plan for the season. While you may to stay in the verdant vineyards in September, it will likely come at a price because it’s during the harvest. By contrast, you may be able to find some really fantastic deals if you come during off season. There may be less wineries and restaurants open, but you can have a truly memorable experience.

The Corner Nest – Apartment in Montalcino

I spent a lot of time trying to find the best place to stay in the Montalcino old town. Tom REALLY wanted to stay in the town, and I really didn’t want to stay in a lackluster hotel. Ultimately, given our propensity for off-season travel, we ended up renting an apartment. (This made Tom VERY happy, and it’s become the fastest way to make him happy if we’re going to Montalcino.) We’ve stayed at The Corner Nest in Montalcino three times, and we’re already booked for a fourth stay. The Corner Nest is a three-story one-bedroom apartment within the city walls of Montalcino. It’s on the edge of the old city and the bedroom overlooks the Tuscany countryside. (It’s also where I saw the Northern Lights for the first time!) The kitchen overlooks one of the old city gates.

Antonio, an architecture in Montalcino has two properties across the street from each other – The Corner Nest and the Panoramic Nest. He is SO very personable and kind, and he is always as accommodating as possible. I know that a lot of people like the contactless options for vacation rentals, but there really is something lovely about having someone meet you, show you how everything works, and make sure you’re comfortable for your stay. Give me more human interactions please!

Anyway, the apartment has a kitchen and a half-bathroom is on the ground floor. It has a hightop table and two doors that lead to the back of the property (which offers a small sitting area where you can enjoy a glass of wine and a view). You have everything you need to cook your meals at home, including a dishwasher! Antonio includes a lot of extras that you would normally have to bring – like laundry detergent. The apartment has a washer/dryer combination, which is very European and very helpful at times.

On the second floor, there is a living room with a couch and a desk. It’s not quite as naturally well-lit as the ground floor, but there are lamps and you can make it work for zoom calls. (This apartment is very functional if you need to work and wine.) On the third floor, you find the the bedroom and larger bathroom with a walk-in shower. Antonio includes towels, shampoo, and body wash in the apartment. I was impressed with how fluffy and soft the towels were, and there is plenty of hot water with good water pressure. I found the bed and pillows to be comfortable enough.

There is shelving available so you can unpack and there are more than enough hangers. Further, the bedroom has a large window that can be opened, and it offers beautiful views of the sunrise… and if you’re really lucky (like me!), the Northern Lights. (How lucky that I did not close the shutters…!!!) The bedroom doesn’t face the street, so you don’t get much of the road noise at night. This is probably the quietest area in Montalcino with some of the best views of the countryside.

Parking is included, but it is about a 10-minute walk from the apartment. You can load and unload your car at the apartment though. (Sometimes you can find street parking, though it’s just easier to use the parking passes that Antonio provides.)

Altesino Suites – Apartments near Montalcino

Within a 15 minute drive from the town of Montalcino, Altesino Suites have full apartments available within the vineyards of Montalcino. Their apartments, or suites, are named after colors and are indicative of what to expect. We booked the yellow suite, and it was a yellow suite! Similar to The Corner Nest, Altesino Suites feel traditional and rustic, but they offer a few upgraded touches.

We booked a one-bedroom apartment that had a small living area and a full kitchen. The bedroom had a ceiling fan, one of the first I’ve ever seen in Italy. (You would definitely need it the summer.) As a self-proclaimed bed snob (and someone whose body demands a good bed), it was not super comfortable. It was doable for a few days, but it was not great. The bathroom did make up for that with a large walk-in shower with good water pressure and plenty of hot water. There was plenty of storage space available to fully unpack. Some of the apartments have small private pools, which are available for use during the summer. (It was far too cold when we were there.)

I think the staff at Altesino are one if it’s greatest assets. They are extraordinarily kind. We took advantage of a complimentary tasting of the Altesino wines (rosso di Montalcino, Brunello di Montalcino, and Super Tuscan) during our stay. They provided us a quick tour of the vineyard and the cellar, and we really enjoyed chatting with the staff.

Frescobaldi CastelGiocondo Wine Hotel

Tenuta CastelGiocondo is where you go to slow down. It’s mid-range luxury and a fantastic value for the area where luxury wine resorts can run well over $1,000/night in the off season. It’s not where I would go if I wanted to spend time in Montalcino. We took my mom there in the off-season and it was a quiet place to recharge after spending a few days in Verona and Florence. For the most part, we just stayed at the resort and enjoyed the spa. Breakfast is included with your booking, and we only left for lunch or dinner (there isn’t a full-service restaurant on site) and for wine tastings at Buon Tempo and Castiglion del Bosco. In retrospect, we would have brought picnic provisions to enjoy the fall sunsets at the resort instead of having to drive 25 minutes to Montalcino at night.

The rooms are housed in beautifully restored stone buildings, and the rooms are large, modern, and comfortable. Both our room and my mom’s room included a table and sitting area, a canopy bed (which was VERY comfortable), and modern bathrooms. Our room had both a large walk-in shower and a bathtub, as well as a separate bathroom with dual sinks. Water pressure and hot water were both good. While the room was not exceptionally well-lit, it was definitely cozy and romantic. The windows opened and we had exceptional sunset views.

We didn’t have a lot of interaction with the staff beyond check-in and breakfast. It was very quiet. We found out when we arrived that we needed to reserve the spa. They have a website for that, but it’s not super intuitive. In retrospect, I would have reached out to better understand what to expect and how to book tastings. (Castelgiocondo is one of Tom’s favorite 2018 Brunellos.) It also shares a property with Luce, but we didn’t realize that until we arrived. I think I expected it to be a lot more like the Meneghetti wine hotel, but it was a lot more self-service and hands off than I expected.

Note: The internet in our building wasn’t great and we didn’t have a lot of cell service in the area. It’s pretty remote. However, the internet was better in the spa building, and we moved over there to work. I had a hard time taking phone calls, and we couldn’t effectively use zoom in our room. If you need to work while on vacation, I would not book this hotel. I was a bit stressed while we were there, and when we go back, it will be when we can truly unplug.

Rosewood Castiglion del Bosco – Luxury Tuscany Resort

You already know. There’s nowhere I love more than Castiglion del Bosco. It’s my favorite splurge hotel in Tuscany. For awhile, I had a hard time imagine staying anywhere else. Then I realized that staying at the Rosewood isn’t staying in Montalcino. If I wanted to go to the Rosewood, then I needed to make Montalcino work for Tom. Marriage is about compromise. 🙂 I don’t go to the Rosewood to go to Montalcino though. I go to the Rosewood to stay at the Rosewood. We’ve stayed at Castiglion del Bosco four times since 2022. Tom will tell you. First we came for one night, then we came for two nights, and now we stay for four nights. (I’ve already booked our fifth and sixth stays for 2025, too.)

Everything about Castiglion del Bosco is Tuscan luxury and they pay a lot of attention to details. From weighted blankets, to candles, to dimmer switches, to bath salts, CdB is made for relaxation and comfort. The “standard” junior suite is just as comfortable as their standard suites. Almost all of our suites have been larger than our first apartment together. (They also have villas if that’s your travel style. We’ve heard from our friends in the wine club that it is the most epic way to experience a family vacation in Tuscany, but that’s not necessarily our travel style.)

They’ve thought of everything. The beds are comfortable, the linens are luxurious, and if you forgot anything, it’s already in the room – just in case. There are deep soaking tubs and huge walk-in showers. Bath amenities are from the famous Santa Maria Novella pharmacy in Florence, and I’m obsessed. (The spa also offers a facial with SMN products, and it is fantastic.) You have private terraces with views of the surrounding countryside. I’ve never been anywhere more luxurious, more comfortable, or more relaxing.

The Rosewood Tuscany offers everything from wine tasting, to on-site cooking classes, to truffle hunting, to art classes, and stargazing experiences. In the winter, they have an ice skating rink and a small Christmas village on property. The infinity pool is covered so you can swim throughout the year. They are also happy to organize off-site excursions to wineries, to Florence or Siena, and can customize tours to your interests.

Castiglion del Bosco is best booked with a Rosewood Elite luxury travel agent like me! This can get you free breakfast, a hotel credit for the restaurants or spa, room upgrades, and more!