33 of the Best Wineries in Tuscany, by Distance from Siena House

Southern Tuscany is one of the great wine destinations of the world, and Siena House sits right in the middle of it. Within a short drive you’ll find the cellars of Vino Nobile di Montepulciano, Brunello di Montalcino and the Orcia valley; a little further afield lie the famous estates of Chianti Classico, and beyond them the coastal Super Tuscans of Bolgheri and the Maremma.

To make planning easy, we’ve ordered the wineries below by driving distance from Siena House — starting with the ones closest to our door and working outward to the estates that are worth a longer journey. Every entry includes the address, website and approximate drive time, so you can build a tasting day that suits you.

As your hosts, we know many of these estates personally. If you’re staying with us, just ask — we’re always happy to suggest the right wineries for your taste and to help with bookings, as most require a reservation.

Tuscan Wineries by Distance from Siena House

A quick overview of all 33 wineries, nearest first. Click any name to jump to its full details.

The five great names to know: Vino Nobile di Montepulciano and Brunello di Montalcino (both within an hour, and our local heroes), Chianti Classico from the hills toward Siena and Florence, the white Vernaccia di San Gimignano, and the coastal Super Tuscans of Bolgheri and the Maremma. You don’t need to be an expert to enjoy them — just thirsty and curious.

Closest to Siena House — under 30 minutes

Donatella Cinelli Colombini – Fattoria del Colle, Trequanda

• Address: Località Il Colle, 53020 Trequanda SI, Italy
• Distance from Siena House: 12 km (~15 minutes)
• Website: https://www.cinellicolombini.it/en/
• Instagram: @donatellacinellicolombini

Situated in Southern Chianti, Fattoria del Colle is an enchanting XVIth-century estate that harmoniously blends historic charm with forward-thinking winemaking. Surrounded by 336 hectares of unspoilt countryside, including 17 hectares of vineyards and 6 hectares of olive groves, it provides a picturesque escape into Tuscany’s past and present.

The estate’s historic cellar, built in 1592 by the Socini family, houses a medieval hermitage transformed into a Brunello infernotto, alongside ancient cellars and modern barrel rooms. Unique to Italy, the Casato Prime Donne winery is entirely run by women, reflecting the estate’s dedication to excellence and innovation. Visitors can also enjoy the estate’s vineyards, olive groves, and the latest addition: a video room offering virtual vineyard experiences.

Montemercurio, Montepulciano

• Address: Via di Totona, 25, 53045 Montepulciano SI, Italy
• Distance from Siena House: 17 km (~20 minutes)
• Website: https://www.montemercurio.com/en/
• Instagram: @montemercurio_winery

Montemercurio’s legacy began in the early ’60s when Grandfather Damo planted the first vine, laying the foundation for a remarkable winemaking journey. Today, the Anselmi family has expanded this vision, growing the vineyard to 10 hectares dedicated to producing quality wines that honor the land and tradition of Montepulciano.

The “Vino Nobile Damo D.O.C.G.” stands as a testament to the family’s dedication, reflecting the unique characteristics of the Montepulciano hills. Every step, from manual harvesting to aging in traditional Tuscan barrels, is meticulously carried out to preserve the wine’s intrinsic flavors. Montemercurio also offers a taste of Tuscan tradition with their Vin Santo “1986,” a sweet symbol of the land, perfect for special occasions.

Canneto, Montepulciano

• Address: Via dei Canneti, 14, 53045 Montepulciano SI, Italy
• Distance from Siena House: 17 km (~25 minutes)
• Website: https://www.canneto.com/en/
• Instagram: @canneto_montepulciano

Nestled on the western slopes of Montepulciano, near the iconic church of San Biagio, Canneto offers breathtaking views and a scenic landscape ideal for exploration.

Canneto is a certified organic farm producing top-quality wines, including Vino Nobile di Montepulciano. The estate covers 48 hectares with 31 hectares of vineyards and 4 hectares of olive groves. Canneto’s commitment to organic farming and the use of nitrogen in tastings to preserve wine quality ensure a unique and enriching visit.

The estate’s picturesque location has also been featured in popular media, including Quantico3 and Dolce and Gabbana’s perfume advertisement.

Avignonesi, Montepulciano

• Address: Via Colonica, 1, 53045 Montepulciano SI, Italy
• Distance from Siena House: 26 km (~25 minutes)
• Website: https://www.avignonesi.it/
• Instagram: @avignonesiofficial

Expansive winery surrounded by rolling hills, offering tours & tastings, plus food pairings.

Salcheto Winery, Montepulciano

• Address: Via Villa Bianca, 15, 53045 Montepulciano SI, Italy
• Distance from Siena House: 19 km (~30 minutes)
• Website: https://salcheto.it/en/
• Instagram: @salcheto

Salcheto Winery, rooted in the historic Nobile di Montepulciano region, is renowned for its dedication to Sangiovese, quality, and sustainability. Established in 1984 as a traditional multi-crop farm, Salcheto has evolved into a 60-hectare estate of organic vineyards, all cultivated according to systemic sustainability principles. In 2011, the winery unveiled a new cellar designed for energy efficiency and to enhance the area’s touristic appeal.

The architectural design of Salcheto’s cellar integrates energy-efficient features like vertical gardens, solar skylights, and a biomass power plant. Visitors can explore the Enoteca and Winehouse, located at the heart of the production area, where they can taste wines and enjoy brunches inspired by the estate’s vegetable gardens.

Croce di Febo, Montepulciano

• Address: Via Fontelellera, 19/a, 53045 Montepulciano SI, Italy
• Distance from Siena House: 20 km (~30 minutes)
• Website: https://www.crocedifebo.it/en/
• Instagram: @croce_di_febo

Nestled in Montepulciano, Tuscany, Croce di Febo at the “Pietra del Diavolo” farm invites you to explore their vineyards and learn about their commitment to biodynamic farming and biodiversity. This family-run estate cultivates just over 4 hectares of vineyards in two plots, each with a unique terroir, creating a distinctive character in their wines.

Experience the natural wine expressions of the land through an intimate wine tasting session. Taste the Rosso di Montepulciano, Vino Nobile di Montepulciano, and one of their Tuscan IGTs. The biodynamic approach ensures a sensitive balance with nature, enhancing the purity and authenticity of their wines. Tastings are private and must be booked in advance, providing a personalized and educational experience.

Fèlsina, Castelnuovo Berardenga

• Address: Via del Chianti, 101, 53019 Castelnuovo Berardenga SI, Italy
• Distance from Siena House: 37 km (~30 minutes)
• Website: https://www.felsina.it/en/
• Instagram: @felsina_wines

Founded in 1966 by Domenico Poggiali, Fèlsina represents a harmonious blend of tradition and modernity. Known for their commitment to quality and innovation, the Fèlsina team has crafted some of Tuscany’s finest wines, including the renowned Fontalloro and Rancia. Their dedication extends beyond wine to olive oil production, ensuring a holistic approach to terroir.

Fèlsina is strategically located on the southeastern edge of the Chianti Classico appellation, where the Chianti hills meet the Ombrone valley. This extensive estate spans 600 hectares, with 95 hectares dedicated to vineyards. This unique positioning makes Fèlsina a “frontier land,” bridging the Chianti Classico and Crete Senesi areas towards Montalcino.

The estate offers an immersive experience into the world of Chianti Classico, with picturesque views stretching from the Chianti hills to the Crete Senesi, making it a must-visit for wine enthusiasts.

A short drive — 30 to 45 minutes

Sasso di Sole, Montalcino

• Address: 53024 Torrenieri, Province of Siena, Italy
• Distance from Siena House: 31 km (~35 minutes)
• Website: https://www.sassodisole.it/

The Terzuoli family, with a winemaking legacy dating back to the seventeenth century, embodies generations of wisdom and experience. Combining technological innovation with respect for tradition, they produce high-quality wines from their ten hectares of Sangiovese Grosso vineyards in Montalcino, nestled within the UNESCO park of Val d’Orcia.

At an elevation of 280 to 320 meters, with south/south-west exposure and medium-textured, stone-laden soil, these vineyards yield grapes perfect for structured wines with long aging potential. The winery employs slow fermentation with indigenous yeasts, followed by malo-lactic fermentation in steel tanks. Tradition permeates their barrel room, where large Slavonian oak barrels preserve the wine’s integrity and enhance its elegance.

San Felice, Castelnuovo Berardenga

• Address: Località S. Felice, 1, 53019 Castelnuovo Berardenga SI, Italy
• Distance from Siena House: 46 km (~40 minutes)
• Website: https://www.sanfelice.com/en
• Instagram: @sanfelice_official

San Felice is a prestigious wine estate located in the heart of Chianti Classico, just minutes from Siena. The estate spans over 600 hectares at an altitude of 400 meters, offering ideal conditions for producing highly acclaimed wines and oils.

Visitors can explore the 18th-century cellars, taste wines at the contemporary enoteca, and enjoy tours of the vineyards. San Felice is renowned for creating Vigorello, the first Supertuscan, and continues to produce exceptional wines with a commitment to quality and tradition.

Tenuta di Arceno, Castelnuovo Berardenga

• Address: 53010 Localita Arceno, 53019 San Gusmé SI, Italy
• Distance from Siena House: 42 km (~40 minutes)
• Website: https://www.tenutadiarceno.com/en
• Instagram: @tenutadiarceno

Tenuta di Arceno, an ancient Tuscan estate, boasts a rich winemaking heritage dating back to the 16th century. Nestled at the southernmost edge of Chianti Classico in Castelnuovo Berardenga, this estate produces high-quality wines that celebrate both native Sangiovese and international varieties. The estate spans 1,000 hectares, with 92 hectares dedicated to vineyards and 50 hectares to olive orchards.

Tenuta di Arceno’s diverse wine portfolio includes three Chianti Classico DOCG wines centered on Sangiovese and three Toscana IGT wines showcasing international varieties like Cabernet Franc, Merlot, and Cabernet Sauvignon. The picturesque vineyards, set against the backdrop of the ancient town of San Gusmè, provide a stunning setting for wine enthusiasts.

Vallepicciola, Pievasciata

• Address: SP 9 di Pievasciata, 21, 53019 Pievasciata SI, Italy
• Distance from Siena House: 52 km (~40 minutes)
• Website: https://www.vallepicciola.com/en/
• Instagram: @vallepicciola

In the late 1990s, the Bolfo family revitalized an old monastery into the prestigious Hotel Le Fontanelle, from which Vallepicciola’s story began. The estate spans 265 hectares, featuring centuries-old woods, over 4,000 olive trees, and 107 hectares of meticulously cultivated vineyards.

Caparzo, Montalcino

• Address: Strada Provinciale del Brunello, 53024 Montalcino SI, Italy
• Distance from Siena House: 40 km (~45 minutes)
• Website: https://www.caparzo.com/
• Instagram: @caparzo_winery

Caparzo is a place that captures your heart even before you understand why. Situated in the serene, green expanse of Montalcino, it offers a perfect escape from the hustle of big cities. The Terroir of Montalcino, with its unique blend of barren clays, golden tuffs, and lush vegetation, is beautifully reflected in every glass of wine produced here.

Since its founding in the late 1960s by a group of friends passionate about Tuscany and wine, Caparzo has grown into a celebrated producer of Brunello di Montalcino.

Cantina di Montalcino

• Address: Loc. Val Di Cava, 53024 Montalcino SI, Italy
• Distance from Siena House: 42 km (~45 minutes)
• Website: https://cantinadimontalcino.it/en/
• Instagram: @cantinadimontalcino

Cantina di Montalcino, established in 1970, stands as the only cooperative winery in the renowned Brunello region. Located on a hilltop in the ancient village of Montalcino, this winery benefits from the unique pedoclimatic characteristics of the area. The 94 small farms that make up the cooperative cultivate 160 hectares of vineyards, producing top-quality grapes for wines like Rosso di Montalcino DOC and Brunello di Montalcino DOCG.

The winery itself is a marvel of architecture, designed to echo the rolling Tuscan hills. Part of the Toscana Wine Architecture circuit, it seamlessly blends traditional winemaking with modern design. Nestled in a UNESCO World Heritage site, Cantina di Montalcino offers an immersive experience amidst stunning landscapes of meadows, olive trees, and vineyards.

Fattoria dei Barbi, Montalcino

• Address: Loc. Podernovi, 170, 53024 Montalcino SI, Italy
• Distance from Siena House: 42 km (~45 minutes)
• Website: https://www.fattoriadeibarbi.it/en/
• Instagram: @fattoriadeibarbi

Owned by the Cinelli Colombini family since 1352, Fattoria dei Barbi is one of the most historic and renowned wineries in Montalcino. With a legacy spanning over six centuries, this estate is a testament to the rich tradition and innovative spirit of Tuscan winemaking. The property covers 350 hectares in Montalcino, Scansano, and Chianti, and has been producing award-winning Brunello since 1892.

Visitors to Fattoria dei Barbi can explore the historical ageing cellars, which house over 300 wooden wine barrels and thousands of bottles of Brunello. The cellar tours offer a unique opportunity to understand the vinification process, the art of ageing wine, and the storied history of the estate. Highlights include the collection of bottles dating back to 1870, making it the most complete wine collection in Italy.

Ricasoli 1141 Winery at Castello di Brolio

• Address: SP484, 18, 53013 Gaiole in Chianti SI, Italy
• Distance from Siena House: 48 km (~45 minutes)
• Website: https://www.ricasoli.com/en/
• Instagram: @ricasoli1141

Ricasoli 1141 Winery, nestled within the historic Brolio Castle, is the quintessential Chianti Classico wine producer. Spanning 1,200 hectares, this estate boasts nearly 240 hectares of vineyards and 26 of olive groves, creating a vibrant landscape of colors around the castle. Under the innovative leadership of Baron Francesco Ricasoli since 1993, the winery has embraced sustainable practices, including meticulous soil studies and the clonal selection of Sangiovese.

The family’s deep historical roots, dating back to Emperor Charlemagne’s court, and their pivotal role in the birth of Chianti wine in 1872, add a rich historical backdrop to the winery’s modern achievements.

A day out — 45 to 75 minutes

Poggio Antico, Montalcino

• Address: Loc. Poggio Antico, 53024 Montalcino SI, Italy
• Distance from Siena House: 43 km (~50 minutes)
• Website: https://www.poggioantico.com/en/
• Instagram: @poggioanticowinery

Nestled on the highest hills of Montalcino, Poggio Antico’s vineyards cover 35 hectares (86 acres) at an impressive altitude of almost 500 meters (1,640 ft). The calcareous rock and galestro (marl) soils force the Sangiovese grape to express its finest qualities, resulting in complex and elegant wines, particularly their iconic Brunello.

Poggio Antico offers a unique experience in Tuscany, providing stunning views from its elevated position. Visitors can explore the meticulously managed vineyards and cellar, gaining insights into the winemaking processes. The tours conclude with a tasting of their exquisite wines. The estate’s Wine Shop, housed in a beautifully renovated ancient building, balances modern functionality with classic Tuscan charm.

Poggio Antico’s Brunello gained international fame when President Obama gifted a reserve bottling to Speaker Boehner, highlighting its prestige and exceptional quality.

Podere di Pomaio, Arezzo

• Address: 19 Località Pomaio, 52100 Arezzo AR, Italy
• Distance from Siena House: 44 km (~50 minutes)
• Website: https://www.pomaio.it/en/
• Instagram: @pomaio_wines

Walking into Podere di Pomaio is a unique experience. Nestled on a 550-meter plateau above Arezzo, this estate offers a breathtaking view and an eco-designed cellar. Guests can savor organic wines and enjoy the colorful vineyards that dominate the valley. The star attraction is the Sangiovese cru, Porsenna, known for its elegance and rare mineral taste.

Podere di Pomaio combines ancient traditions with modern sustainability. The winery, built with sandstone boulders, breathes naturally without extra energy consumption. Visitors are treated to a detailed wine tour, which includes a walk through the vineyards, a visit to the bio-architecture cellar, and a tasting session on the upper floor with panoramic views.

The estate produces 15,000-20,000 bottles annually, mainly from Sangiovese and Merlot, showcasing the unique terroir with wines like Pomaio Origini, Chianti D.O.C.G., Clante, and the celebrated Porsenna.

Castiglion del Bosco, Montalcino

• Address: Località, 53024 Castiglion del Bosco SI, Italy
• Distance from Siena House: 47 km (~60 minutes)
• Website: https://wine.castigliondelbosco.com/?lang=en
• Instagram: @castigliondelbosco

Nestled within a UNESCO-listed Natural Park, Castiglion del Bosco is an exquisite estate that boasts the beauty of rolling hills, lush forests, and scenic ridge-lines. With a history dating back to 1100 A.D., the estate has been transformed by Massimo and Chiara Ferragamo into a top-tier winery, renowned for its exceptional Brunello di Montalcino and hospitality.

Visitors can explore the picturesque Capanna vineyard and indulge in a variety of wine tours and tastings, including barrel tastings, cheese pairings, and vertical tastings of rare vintages.

Podere Le Ripi, Montalcino

• Address: 53024 Montalcino, Province of Siena, Italy
• Distance from Siena House: 50 km (~60 minutes)
• Website: https://www.podereleripi.com/
• Instagram: @podereleripi

Led by Francesco Illy of the Illy coffee family, this biodynamic winery offers a unique blend of tradition and innovation. Known as an “ORGANISMO AGRICOLO,” the farm embodies a holistic approach, considering not just the land and its produce, but the entire ecosystem. For over a decade, Podere le Ripi has adhered to biodynamic farming principles, reminiscent of old farmhouses where communities cultivated with deep respect for nature.

Our wine tours and tastings are private and require reservations, ensuring a personalized and quality experience. Guided by our team of wine experts, winemakers, cellar masters, and agronomists, you’ll explore the farm from the vineyards to the wine cellar, concluding with a choice of two wine tastings.

In 2019 we were named one of the 12 best Wine Tours and Tastings around Florence by Condé Nast Traveler.

Banfi, Poggio alle Mura

• Address: Castello di Banfi, 53024 Poggio alle Mura SI, Italy
• Distance from Siena House: 52 km (~60 minutes)
• Website: https://www.banfi.it/hospitality/
• Instagram: @castellobanfi_wineresort

Banfi, founded in 1978 by the Italian-American Mariani brothers, John and Harry, has grown into a state-of-the-art winery known for its premium wines. Situated south of Montalcino, the estate spans 7,100 acres, with vineyards, olive groves, fruit trees, and woodlands.

Banfi is celebrated for its innovative approach, incorporating advanced technology and rigorous research to enhance winemaking processes. The estate’s dedication to quality is evident in its projects, including clonal studies of Sangiovese and the development of their “Horizon” microvinification area. Banfi’s wines, particularly their reds, undergo meticulous vinification and aging in over 7,000 customized barrels, ensuring strength, elegance, and longevity.

Castello di Fonterutoli – Marchesi Mazzei, Fonterutoli

• Address: Via Ottone III di Sassonia n. 5 Loc, 53011 Fonterutoli SI, Italy
• Distance from Siena House: 70 km (~60 minutes)
• Website: https://eu.mazzei.it/
• Instagram: @marchesimazzei

Castello di Fonterutoli has been under the stewardship of the Mazzei family since 1435. This rich legacy, paired with half a century of Sangiovese research, enables the estate to produce wines of exceptional diversity and complexity. Spanning 650 hectares, with 117 hectares dedicated to vineyards, the estate meticulously manages 120 different parcels located between 230 and 500 meters above sea level.

Castello di Fonterutoli’s state-of-the-art cellar enhances each parcel’s unique characteristics through separate vinification and aging processes. The winery employs gravity in its winemaking, using a three-level system to allow grapes to “drop” naturally during various stages, ensuring minimal handling. The underground cellar, maintaining a consistent temperature and humidity naturally, houses over 3,000 oak barrels, where wines develop their complexity and smooth, elegant tannins. The estate offers eight distinct wines, including three Chianti Classico and five IGT Toscana.

Castellare di Castellina

• Address: Località Caselle, SP130, 53011 Castellina in Chianti SI, Italy
• Distance from Siena House: 76 km (~60 minutes)
• Website: https://www.castellare.it/en/castellare-di-castellina/
• Instagram: @castellarewine

Situated in the heart of the Chianti Classico region, Castellare di Castellina spans 80 hectares, with 33 hectares dedicated to vineyards and 20 to olive groves. The vineyards form a natural south-east facing amphitheater at an average height of 370 meters, producing well-structured, intense wines perfect for aging.

The winery, known for its pioneering use of small French oak barrels, offers a unique experience with its combination of concrete and steel tanks, following the principles of renowned winemaker Giacomo Tachis. Each year, the labels feature a different rare bird, reflecting the estate’s commitment to nature.

Castello Nipozzano-Frescobaldi, Florence

• Address: Località Nipozzano, 50060 Nipozzano FI, Italy
• Distance from Siena House: 96 km (~75 minutes)
• Website: https://www.frescobaldi.com/en/estates/castello-nipozzano
• Instagram: @marchesifrescobaldi

Castello Nipozzano, the ancient defensive stronghold of Florence dating back to the year 1000, is the most celebrated and historic property of the Frescobaldi family. Known for its lack of water, the area is ideal for grapevine cultivation. Renowned since the Renaissance, artists like Donatello and Michelozzo Michelozzi frequently purchased wine from this estate.

Nestled in the vineyards and hills of Chianti Rufina, just 20 minutes from Florence, Castello Nipozzano offers an authentic Tuscan experience. The castle’s ancient underground cellars invite guests for a tasting of the estate’s wines, including the prestigious Mormoreto, produced from vines cultivated since 1855.

Antinori nel Chianti Classico

• Address: Via Cassia per Siena, 133, 50026 Bargino FI, Italy
• Distance from Siena House: 100 km (~75 minutes)
• Website: https://www.antinori.it/en/
• Instagram: #antinorichianticlassico

Antinori nel Chianti Classico, inaugurated in October 2012, stands as a testament to the Antinori family’s deep-rooted connection to their ancestral lands. This architectural marvel was crafted with local materials like terracotta, wood, corten, and glass, reflecting the earthy tones of its surroundings. Designed for low environmental impact and energy efficiency, the winery integrates gravity flow vinification and optimal conditions for wine production and aging.

Its unique design features a facade that blends seamlessly into the Tuscan landscape, highlighted by an impressive spiral staircase linking its three levels. Voted the world’s top vineyard in 2022, it welcomes visitors to explore its terraces amidst vineyards of Sangiovese and other historic varieties, offering a direct engagement with Antinori’s philosophy of quality-driven, passionate wine production.

Tenuta Ruffino Poggio Casciano

• Address: Via Poggio al Mandorlo, 1, 50012 Bagno a Ripoli FI, Italy
• Distance from Siena House: 100 km (~75 minutes)
• Website: https://www.ruffino.it/
• Instagram: @ruffino_1877

Ruffino is one of Tuscany’s most renowned wine labels, celebrated for its consistency and quality across a vast selection of wines sourced from growers throughout the region. With numerous estates under its umbrella, Ruffino has established itself as a leading name in Chianti production.

Tenuta Ruffino Poggio Casciano offers a perfect blend of Renaissance charm and modern elegance. Nestled in the Tuscan hills near Florence, this 14th-century villa features stunning grounds and an impressive underground barrique tunnel used for soil and microclimate research.

The vineyards, situated at 320 meters, cultivate Sangiovese, Cabernet Sauvignon, Cabernet Franc, and Merlot, producing iconic labels like Modus Toscana IGT and Alauda Toscana IGT.

Worth the journey — the coast & Maremma

Castello ColleMassari, Maremma Toscana

• Address: Localita, 58044 Poggi del Sasso GR, Italy
• Distance from Siena House: 74 km (~90 minutes)
• Website: https://collemassari.it/
• Instagram: @collemassari

Nestled near Cinigiano in the foothills of Mount Amiata, ColleMassari sits at an altitude of 320 meters above sea level, offering a picturesque view of the Montecucco DOC. The estate, named after the 14th-century Castle of ColleMassari, boasts a modern cellar built with bioarchitecture principles and a gravity flow system to ensure gentle wine production.

Visitors to ColleMassari can embark on a captivating journey through the wine world, starting with a tour of the innovative cellar and concluding with a tasting session in a dedicated room that offers stunning views of the castle and surrounding vineyards. The estate features primarily Sangiovese grapes, with aging done in large Slavonian oak casks, barriques, and tonneaux. Additionally, the nearby Tenuta di Montecucco luxury resort offers a restaurant serving local organic products and the estate’s exquisite wines and olive oil. The entire estate is certified organic, emphasizing sustainability and quality.

Rocca di Frassinello

• Address: Località Poggio la Guardia, 58023 Giuncarico GR, Italy
• Distance from Siena House: 120 km (~90 minutes)
• Website: https://www.castellare.it/en/rocca-di-frassinello/
• Instagram: @roccadifrassinello

Rocca di Frassinello is a prestigious collaboration between Castellare di Castellina and Domaines Barons de Rothschild-Château Lafite, uniting the best of Italian and French winemaking. Located in Gavorrano, this estate spans 500 hectares, with 83 dedicated to vineyards, producing exceptional wines from Sangioveto, Cabernet Sauvignon, Merlot, Syrah, and Vermentino.

Designed by the renowned architect Renzo Piano, the winery is an architectural marvel, seamlessly blending functionality with elegance. The cellar, with its revolutionary space division, relies on gravity for the initial winemaking process, preserving grape quality. Visitors can explore the impressive barrel room illuminated by a sun-capturing tower, and the modern pavilion perfect for tastings and events. The estate also features an Etruscan archaeological site and stunning terracotta terrace offering panoramic views of the Maremma hills.

Le Mortelle – Marchesi Antinori, Maremma Toscana

• Address: 58043 Ampio, Province of Grosseto, Italy
• Distance from Siena House: 135 km (~90 minutes)
• Website: https://www.antinori.it/en/tenuta/estates-italy/le-mortelle-estate/
• Instagram: @marchesiantinori

Located in the heart of Maremma Tuscany, Le Mortelle estate, just a few kilometers from Castiglione della Pescaia, offers an exceptional combination of natural beauty and historical heritage. Owned by the Antinori family since 1999, the estate spans 270 hectares, with 170 dedicated to vineyards.

Le Mortelle is renowned for its state-of-the-art underground winery, designed to blend seamlessly with the surrounding environment. Visitors can explore the cylindrical three-story structure, featuring an impressive helical staircase and a living green roof. The tour covers grape reception, fermentation vats, and the stunning barrel cellar, culminating in a wine tasting experience.

Tenuta Ammiraglia-Frescobaldi, Maremma Toscana

• Address: Località La Capitana, 58051 Montiano GR, Italy
• Distance from Siena House: 140 km (~2 hours)
• Website: https://www.frescobaldi.com/en/
• Instagram: @marchesifrescobaldi

Located in the heart of the Maremma, Tenuta Ammiraglia epitomizes contemporary Mediterranean Tuscany. Designed by architects Piero Sartogo and Nathalie Grenon, the estate blends seamlessly with the landscape, embodying the harmony of modernity and nature.

Tenuta Ammiraglia is a haven for wine lovers seeking fresh, mineral-rich wines influenced by the sea. The estate’s innovative architecture resembles a ship’s bow, pointing towards the Tyrrhenian Sea, symbolizing the discovery of new horizons. Visitors can enjoy personalized tours and tastings, explore the verdant, technology-enhanced cellar, and savor local cuisine. Signature wines include Alìe Rosé, Massovivo Toscana IGT, Terre More Maremma Toscana Cabernet DOC, and the iconic Aurea Gran Rosé Toscana IGT.

Caiarossa, Riparbella

• Address: Strada Comunale di Montescudaio, 59, 56046 Riparbella PI, Italy
• Distance from Siena House: 133 km (~2 hours)
• Website: https://www.caiarossa.com/en/
• Instagram: @caiarossa

Caiarossa, nestled in the hills of Riparbella, is a 100-hectare estate blending the ancient wine-making traditions of Tuscany with biodynamic principles. Established in 1998, Caiarossa boasts 40 hectares of vineyards alongside olive groves, forests, and wildflower meadows. The Albada Jelgersma family, who also own Bordeaux estates Château Giscours and Château du Tertre, acquired Caiarossa in 2004, bringing their passion and expertise to this vibrant terroir.

Caiarossa offers a unique fusion of oenological precision and natural beauty, from its eco-friendly winery designed with Feng Shui principles to its breathtaking views of the Tyrrhenian Sea. Visitors can explore the estate, learn about biodynamic farming, and enjoy wine tastings that showcase the diverse expressions of its eleven different grape varieties.

Prima Pietra, Riparbella

• Address: loc. i Prati, 56046 Riparbella PI, Italy
• Distance from Siena House: 140 km (~2 hours)
• Website: https://www.tenutaprimapietra.com/en/
• Instagram: @primapietra

Nestled in the serene, picturesque village of Riparbella, Prima Pietra offers an escape from the bustling tourist spots of Bolgheri. This tranquil estate, purchased by Massimo Ferragamo, has been crafting exceptional Bordeaux blends since 2007. The vineyard is surrounded by Mediterranean scrub and boasts a high, windy location ideal for organic viticulture.

Visitors can explore the state-of-the-art cellar, renovated within a centuries-old farmhouse, and enjoy guided tours and tastings.

Tenuta San Guido, Bolgheri

• Address: Località Capanne, 27, 57022 Bolgheri LI, Italy
• Distance from Siena House: 145 km (~2 hours)
• Website: https://www.tenutasanguido.com/en
• Instagram: @tenuta_sanguido

Tenuta San Guido is a legendary estate, celebrated as the birthplace of the iconic Sassicaia wine, one of Italy’s original Super Tuscan wines. Established in the 1940s and nestled in the heart of Maremma, this estate has thrived under the stewardship of the Incisa della Rocchetta family, combining a rich historical legacy with modern innovation.

Renowned for its unique terroir and the microclimate created by the surrounding hills and sea breezes, Tenuta San Guido produces three exceptional wines: Sassicaia, Guidalberto, and Le Difese. Each wine represents a different expression of the estate’s diverse land.

Ornellaia, Bolgheri

• Address: Località Ornellaia, 191, 57022 Bolgheri LI, Italy
• Distance from Siena House: 150 km (~2,5 hours)
• Website: https://www.ornellaia.com/en/
• Instagram: @ornellaiawinery

Founded in 1981, Ornellaia is a testament to vision and determination, immediately embarking on a quest for excellence under the ownership of the Frescobaldi family. The estate, overseen by Marchese Ferdinando Frescobaldi and CEO Giovanni Geddes da Filicaja, embodies timeless elegance and the Italian lifestyle. The Ornellaia Archivio Storico, inaugurated in 2017, continues to chronicle the estate’s prestigious history.

Ornellaia’s vineyards, extending between Bolgheri and the coast, benefit from diverse soils—marine, alluvial, and volcanic—producing exceptional wines from varieties like Cabernet Sauvignon, Merlot, Cabernet Franc, and Petit Verdot. The estate also cultivates white varieties, creating a unique portfolio of elegant wines.

Visitors to Ornellaia can expect a guided tour that reveals the estate’s historical vineyards and contemporary cellar, showcasing the Vendemmia d’Artista project. The barrique cellar, where French oak barrels age the estate’s blends, leads to the Archivio Storico, the estate’s heart.

Planning Your Tuscan Wine Tour from Siena House

With Vino Nobile di Montepulciano, Brunello di Montalcino and the Orcia valley all within easy reach — and Chianti Classico and the coast within a day’s drive — Siena House makes an ideal base for exploring Tuscan wine at your own pace. Most estates require a reservation, and a car is essential to reach them; if you’d rather not drive between tastings, we can help arrange a local driver.

As your hosts, we know many of these estates personally — some are intimate and personal, others grand and easy to visit at short notice. If you’re staying with us, just ask for our recommendations and we’ll help make your wine tour truly memorable. Ready to plan your trip? Choose your room or explore more of the area in our Tuscany Guide.