11 Best Winery Hotels in Tuscany Italy

Tuscany is wonderful in every season. This vibrant landscape in the heart of Italy blossoms with life and color, and vineyards are its crown jewels. Think vineyards beginning to burst with color, mauve wisteria cascading down weathered stone walls, and wildflowers scattered across meadows. What’s more, every corner of the region holds a chapter in its winemaking legacy, which is what makes staying at these age-old wineries all the more special. The best and most well-known winery hotels in Tuscany, Italy, are scattered throughout the countryside. Think a smattering of ancient Borghi (hamlets/villages), some transformed into elegant wine resorts, while others are home to smaller Relais and a handful of local residents.

No matter where we went, these winery stays all offered a taste of the rural Tuscan life, with a deep connection to the landscape, warm hospitality, sweeping vineyard views, and an amazing list of wines. What’s more, they had not only the well-known varieties such as Cabernet Sauvignon and Sangiovese, but they also championed lesser-known indigenous grapes that produced exceptional labels. Here’s a roundup of the best vineyards to stay at in Tuscany.

Badia a Coltibuono, Siena

11

Looking like the backdrop of a Raffaello painting, the ancient Benedictine abbey-turned-winery stay Badia a Coltibuono, has a long and rich viticulture history. In fact, a recent archaeological dig ended up unearthing Romano-Etruscan grape seeds that are more than two millennia old! Up here, time stands still, and we could too — while unwinding and sipping on wine, of course. Did we mention that its origins go back to 1051 and it’s the first winery in Chianti? Yes!

Our tasting excursions took place in the wine library, which included not only a mellow Vin Santo but also some excellent organic olive oils. In fact, our advanced tasting excursions even included bruschetta and charcuterie. What’s more, we also explored the ancient cantinas, picnicked amongst the cineyards, and rested in the shady cloisters. Moreover, they also offered unique Tuscan cooking class experiences in their historic family kitchen. The star, though, is the outdoor pool or the magnificent Italian garden with the private hydromassage pool. Sigh. Finally, the staff take pride in the place and are knowledgeable and very attentive.

We had the choice of a handful of rooms, which were formerly the monks’ quarters, and four simple apartments. Not only did they retain original features, but they also had all modern creature comforts for living, including Wi-Fi, which was also available in all the common areas.

Al Gelso Bianco

10

When you think of hotels in Tuscany wine country, you’d hardly think anything will be kid-friendly, right? The stunning country resort Al Gelso Bianco proves that wrong. Perfectly balancing tradition and modern comfort, this 2005-founded modern farm holiday resort sits on a historic estate, offering luxury stays, authentic Tuscan experiences, and wine-tasting. Choose from a gamut of one- and two-bedroom apartments, which can either be on the ground floor or the first floor. What’s more, they’re all decked out in an utterly modern way, with fully-equipped kitchenettes to cook meals since there’s no restaurant on the property. Moreover, they also have free Wi-Fi, garden views, private bathrooms, and wonderful balconies.

View this post on Instagram

A post shared by Al Gelso Bianco (@al_gelso_bianco)

What makes this estate so kid-friendly is that they have family-friendly tours of their working vineyard and olive groves, complete with tastings of the estate’s olive oils and wines! What’s more, they also had family cooking classes every day with expert Tuscan chefs. If that wasn’t enough, they even had truffle hunting, farm-to-table dining experiences, and opportunities for scenic bike rides as a family. Did we mention they even had pasta-making classes? Yes! Moreover, the property has a stunning kid-friendly swimming pool, which comes with sweeping views of the vineyards. Besides a spa, this resort even served sumptious breakfasts every day. What more could we ask for?

Villa Le Prata, Siena

9

Most romantic. We were looking for sunset views and intimate wine tastings, which is why we chose Villa Le Prata. This extraordinary 1862-built oasis was the former hunting lodge of Count De Vecchi and the official country residence of Montalcino’s Bishop before taking on the form of this winery hotel.

Today, this stunning escape is surrounded by olive groves and iconic vineyards, which produce the locally produced and iconic Brunello di Montalcino wine. Not only were we able to sample it during the amazing wine tasting tours, but we were also able to enjoy it all over the property. For instance, we could relax poolside and sip on the wine, or even have it as part of special request meals, which we could enjoy on the lush grounds. We even enjoyed a gourmet picnic amidst the cypresses and the olive groves and an alfresco meal under the stars, all paired with the estate’s wines, of course. The best bit? The limited area of the vineyards translates into the wine’s exclusivity.

Staying here was as romantic as it got, with the limited-edition eight rooms and suites featuring luxurious details. Furthermore, they boasted prestige, comfort, and refined and authentic furnishings. For instance, the Bishop’s room, featured red walls and blended religious furnishings with mod-cons, with the dominating feature being the 17th-century golden-leaf bed.

Villa Dievole Wine Resort, Siena

8

Oldest winery. Perhaps the oldest winery on this list is the Villa Dievole Wine Resort, as Dievole has been making wine — on and off — since the year 1090! Not only is it a hotel now, but it also has a whopping 16 working vineyards across 80 hectares! The 18th-century Hamlet-turned-luxe wine estate is its latest addition, and we were thrilled to be staying here. In terms of experiences, the classic guided tours offer not only wine tastings but even olive oil tastings! So, if you’re hoping to come back from your Italian holiday after having learnt a bit of Italian cooking, this is where you should be.

We loved how the architect has reimagined the Dievole’s digs in the form of a creamy dreamscape: think linens and furnishings in pale hues, marble bathrooms, stone floors, and whitewashed ceilings. Pops of color come from the gorgeous wall-mounted Medici-style still-lifes. The signature restaurant, Novecento, is already making waves with its menu that features award-winning olive oil, local meats and cheeses, and seasonal fruit. Did we mention the traditional Tuscan cooking classes with Chef Monica? Yes!

Casa Ruffino

7

Imagine staying in a gorgeous vineyard that lies just 30 minutes from the center of Florence. Welcome to Casa Ruffino, which sits within the estate of Tenuta Poggio Casciano, bringing together hospitality, art, and wine under one roof. We went on a multi-sensory journey to discover the amazing Ruffino red wines. These included guided tours of the wine cellar as well as curated tastings that allowed us to understand the centuries-old winemaking legacy. Add to that the authentic Tuscan cuisine at the signature Tre Rane Restaurant, and it’s no wonder that this estate is extremely popular with oenophiles. Beyond that, the estate boasted a serene infinity pool that was ideal for relaxing on lazy afternoons.

With just eight rooms and suites to choose from, staying here was as intimate and exclusive as it got. What’s more, all of them faced the vineyards, so whether it was a balcony or a window, we felt as if we’d been transported right into a Tuscan countryside postcard. On the inside, there were classic Tuscan terracotta floors that complemented the modern minimal aesthetics and creature comforts.

Relais Châteaux Il Falconiere & Spa, Arezzo

6

Set inside a stunning, 17th-century Tuscan manor, Relais Châteaux Il Falconiere & Spa overlooks the lush Valdichiana and has wine in its blood, through and through. Owner, host, and Michelin-starred chef Silvia Baracchi is at the helm of this retreat today, which is surrounded by vineyards belonging to the Baracchi family estate. In fact, it was back in 1860 when wine was first produced here! The place reveals itself like a Tuscan fairytale: a cluster of historic structures, including a noble villa, a chapel, a rustic farmhouse, a spa, and two swimming pools tucked amid lavender and rosemary-scented gardens.

The amenities at this Tuscan vineyard stay are befitting of the place. We loved dining at the Michelin-starred restaurant that sat in the refined glass conservatory. It even hosted wine tastings and cooking classes and boasted stunning views. Even the spa had a wine theme; think wine therapy treatments with the leaves and grapes of the vines, as well as the wine itself. Relaxing by the infinity pool was one of the best ways to unwind under the Tuscan sun. If you’re a culinary enthusiast, you’ll love the on-site cookery school that’s helmed by Silvia Baracchi.

Choose from 22 spacious and rather grand rooms and suites. They’re all beautiful and the perfect blend of luxury and homely, and are sprinkled across the lush estate. Moreover, they’re all styled in soft pastel hues and hand-painted details, and some, like ours, even have private balconies with mesmerizing views.

Conti di San Bonifacio — Wine Resort, Grosseto

5

If organic luxe is your taste, then look no further than the Conti di San Bonifacio — Wine Resort. This stunning, five-room Tuscan farmhouse sits in the verdant hills above its own wine estate, making it an incredibly romantic and yet sustainable place to stay — with wine, of course. It wasn’t former Goldman Sachs employee Sarah di San Bonifacio’s intention to create a wine resort. Rather, she wanted a place to spiritually detox with her family. Two decades later, not only does the estate have a couple of award-winning Super Tuscans — Sustinet IGT and Docet — but it’s also an exquisite place to unwind and relax.

We had the choice of seven suites, all of which were decked out in an impeccable and chic manner. Think romantic terraces, open fireplaces, marble bathrooms with deep-soaking bathtubs, and four-poster, muslin-draped beds. They also have Asian antiques and vintage leather chairs, among other modern touches.

Aside from sipping on handcrafted wines and guided tastings, there’s a long list of amenities and activities here. The crown jewel is the infinity pool with incredible views, which is where we enjoyed sipping on wine, too. What’s more, there was also fantastic food at the Maremmana restaurant. Finally, the array of activities can calm even the most frazzled peeps: truffle hunting, mountain biking, ayurvedic massages, meditation, and private yoga.

Borgo San Felice Resort Relais & Châteaux, Siena

4

There can’t be a list of the best vineyard hotels in Tuscany without mentioning a Relais and Chateaux property, can it? Borgo San Felice Resort Relais & Châteaux sits atop a hill in Siena and is surrounded by its own parklands and vineyards. This stunning country house hotel sits in the sun-kissed Piazza San Felice in an authentic and lovingly preserved Italian village, making it a poetic escape.

We had the choice of 33 sumptuously decorated rooms and suites, with vast bathtubs in exquisite bathrooms, huge windows with amazing views, soft furnishings, draped linens, and playful hues.

We drove through rows of immaculately tended vineyards from where come some of the most celebrated wines in the region. Wine is at the heart of this former working village-turned-warm and welcoming resort, which also has two exceptional Mediterranean restaurants and a serene spa. Being a wine estate, vino is at its heart. Firstly, it’s home to a native species, Vigorello, that produced the estate’s first-ever Super Tuscan wine. There’s also the prized Pugnitello and Sangiovese grape variety. We enjoyed tastings both in the winery and the vineyard at sundown. A lovely swimming pool, tennis, billiards, and views for miles — it’s heavenly.

Castello di Vicarello, Grosseto

3

Tucked in the hills of Poggi del Sasso in southern Maremma is the extraordinary Castello di Vicarello. This 12th-century stronghold that looks straight out of a fairytale is a family legacy and a contemporary oenophile’s dream. One of the region’s most beautiful country estates, it’s set across 40 hectares of lush gardens, olive groves, and organic vineyards.

“As lifelong oenophiles, our stay at Vicarello far exceeded our expectations and even delight!”

WOW Travel

Wine is at the very heart of this estate, as their objective is to create a Tuscan version of the Noble Grapes, a.k.a., Bordeaux wines. The three vineyards produce five exceptional labels, which we enjoyed over long, long guided tasting sessions. Other amenities include the spa treatments that showcase the garden’s flowers and herbs, the stunning infinity pool, and e-bikes to explore the region. While there’s the signature restaurant, there’s something special about the alfresco dinners they arrange under the starlight.

Choose from 10 gorgeous suites, which feature a mix of Persian carpets, eastern art, 1920s Florentine club chairs, and Indonesian day beds. They’re complemented by touches like ethnic accents, four-poster beds, antique wood, and velvet upholstery. While Suite Chiesina with its shaded pergola is amazing, our favorite was the Spa Suite, which came with a hammam, a sauna, and a private outdoor jacuzzi carved from an ancient wine barrel!

Castello di Fonterutoli, Chianti

2

Best value for money. We lived like locals at Castello di Fonterutoli in Chianti, a lovely, low-key medieval village tucked at the heart of the Mazzeis’ Chianti Classico estate. The family has been making wine here for as long as 24 generations, and now they’ve turned their attention to hospitality, allowing us a taste of the local Tuscan life.

Attentive and yet low-key service made us feel like a village resident rather than a guest, and the staff helped organize a bunch of activities. Think horse riding, hiking, bike rental, and even cooking classes. Of course, the highlight was a tour of their winery, which included a few delicious tasting sessions. While the local bar-café welcomes both residents and visitors, the vibe at the Osteria is more touristy as it offers heritage dishes (wild game is the focus) with seasonal local produce. Besides free public parking, the standout for us was the swimming pool that lay amidst olive groves.

We had the choice of just 16 simple rooms and suites and 4 traditional apartments, all of which have been renovated for staying. However, they retain their charm with family antiques, terracotta floors, vaulted ceilings, and spectacular views. Modern touches include traditional Tuscan-style lounges and kitchens, coffee tables with books, comfy sofas, and fireplaces.

Il Borro Relais & Châteaux, Arezzo

1

Best overall. The restored medieval village of Il Borro is a former 12th-century stronghold sprinkled with a bit of Ferragamo fairydust. It’s home to the country-chic Il Borro Relais & Châteaux, the crown jewel of this self-sufficient working community. Perched on a rocky outcrop, it’s surrounded by acres and acres of vineyards.

View this post on Instagram

A post shared by Il Borro Toscana (@ilborro)

On the inside, the property boasts 57 rooms and suites, 37 of which are tucked in the medieval village and 20 of which are in newer and independent properties. Solid antiques, neutral hues, and natural materials are peppered throughout, but they’re designed individually in a refined manner. If you’re looking for something special, stay in the grand manor house, the Dimora Storica, or the private villas like Mulino, Casetta, and the discrete Viesca estate.

The estate features multiple experiences for wine lovers, including green wine experiences and even artistic views through winery tours that told us all about the secrets of winemaking. Along with wine tasting, Il Borro’s also offers courses in jewelry and shoemaking. Moreover, the Arte & Vino gallery showcases a collection that includes Warhol, Rembrandt, and Picasso. However, one of our favorite aspects was Il Borro’s resident artisans’ community, who welcome visitors and show them the centuries-old crafts that they keep alive. Traditional luxury amenities include the La Corte spa that offers locally inspired treatments and two restaurants serving delicious Italian cuisine.

Our Verdict!

While we loved all the winery stays in Tuscany, the ones below are our favorites.

• Best overall: Il Borro Relais & Châteaux, Arezzo
• Best value for money: Castello di Fonterutoli, Chianti
• Oldest winery: Villa Dievole Wine Resort, Siena
• Most romantic: Villa Le Prata, Siena

Where to Stay in Tuscany, Italy?

Tuscany has many amazing and well-known cities, such as Florence, Pisa, and La Spezia, to name a few. However, when it comes to winery hotels, it’s the smaller towns and villages where you should be staying. Did you know that Florence happens to be one of the most luxurious honeymoon destinations? Yes!

Firstly, there’s the small, walled medieval hill town of San Gimignano in the province of Siena. It’s one of the best-preserved Italian medieval towns, with gates, city walls, and 14 famous and intact old towers. Next, there’s the alluring Volterra in the province of Pisa, which is famed for its Etruscan origins. Besides vineyards, it also has gorgeous handicraft workshops and shops selling alabaster hand-made objects, which the region is famous for.

Thirdly, there are the walled medieval fortifications and watchtowers of the walled town of Monteriggioni. Boasting views of the beautiful Chianti region, the historic castle complex has people living in it even now. Additionally, this small town also has absolutely enchanting vineyards and wineries. History lovers will love Siena, which is one of medieval Europe’s most important cities. Not only are there many top things to do in Siena, but its historic center is also a UNESCO World Heritage Site. Aside from vineyards, it also has museums, art, cuisine, and more.

Finally, there’s the beautiful Renaissance hilltop town of Montepulciano, which is surrounded by picture-postcard Tuscan vineyards. In fact, the region is considered one of the world’s finest winemaking regions, especially the Vino Nobile di Montepulciano. Moreover, this beloved tourist destination also has hidden corners, charming squares, ancient churches, and elegant Renaissance palaces.

Meanwhile, check out the most beautiful villages in Italy worth visiting.

What should I wear to a vineyard in Tuscany?

Usually, casual daytime tastings allow for more laidback looks, while vineyard dinners are usually more formal and call for chic elegance. Additionally, choose lightweight and breathable fabrics.

How to choose a winery in Tuscany?

Family estates are a great bet, whether they’re medium or even small in size.

What is the oldest winery in Tuscany?

Barone Ricasoli in the province of Siena is the oldest winery in Italy. It’s also the one that created the Chianti Classico.