Maddalena P. Chionne

Published on November 5 2025

Tuscany is a region synonymous with breathtaking landscapes, Renaissance art, and, perhaps most famously, exceptional wine. For the discerning traveler seeking a luxurious and immersive experience, the wine routes offer a journey through history, culture, and, of course, the world's most elite vineyards. This guide highlights the most famous cities along the Tuscan wine routes, from the heart of Chianti to the prestigious hills of Montalcino and the coastal charm of Bolgheri.

Greve in Chianti: The Gateway to Chianti Classico

Nestled in the heart of the Chianti Classico region, Greve has served as the area's primary market town since the Middle Ages. Its history dates to the 11th century, and it gained prominence due to its strategic location on trade routes connecting Florence, Siena, and the Valdarno river markets. This rich commercial past is reflected in its unique triangular piazza, which bustled with merchants and traders for centuries. Today, Greve remains a bustling hub for travelers exploring the storied Chianti region.

Top attractions:

• The central Piazza Matteotti is the town's social heart, surrounded by shops, restaurants, and covered loggias that once hosted merchants.
• A short hike or drive from the main square is the perfectly preserved medieval village of Montefioralle, a walled hamlet offering stunning views and a taste of old-world charm.
• For a culinary deep dive, a visit to the Antica Macelleria Falorni, a historic butcher shop, is essential for sampling local cured meats and other Tuscan delicacies.
• Wine lovers should not miss a tour of the Castello di Verrazzano, the birthplace of explorer Giovanni da Verrazzano, which offers tours and tastings in a historic setting.

Top High-End Hotels:

• Como Castello del Nero: a luxurious stay awaits at this 12th-century castle, offering modern comfort, a world-class spa, and stunning views of the surrounding countryside.
• Villa Bordoni: this boutique hotel provides a romantic and intimate experience, with unique rooms and a peaceful atmosphere.
• Hotel Le Fontanelle: for a five-star experience in the heart of the Chianti Classico region, this hotel offers pristine luxury and scenic tranquility.

High-End Restaurants:

• Vitique: this restaurant is known for its sophisticated and modern approach to Tuscan cuisine.
• Ristoro di Lamole: enjoy excellent food and wine with a view at this restaurant situated in a scenic location just outside of Greve.
• Enoteca Ristorante il Gallo Nero: dine on Tuscan classics like handmade pasta and oak-grilled meats in a charming setting.

Elite Vineyards and Wines:

• Antinori nel Chianti Classico, housed in a spectacular modern building, is a must-visit for its historic roots and exceptional wines.
• Fontodi is a benchmark for high-quality Chianti Classico, with its rich, full-bodied expressions from the renowned Conca d'Oro area.
• The estates of Querciabella and Castello di Ama also produce top-rated Chianti Classico Gran Selezione and are celebrated for their quality and viticultural practices.

Montalcino: The Home of Brunello

Perched on a high hill south of Siena, the medieval town of Montalcino is famous for producing Brunello di Montalcino, one of Italy's most celebrated and age-worthy red wines. In the Middle Ages, the town was largely independent but was eventually absorbed by Siena. However, it served as a refuge for Siena's nobles after the Florentine conquest in 1555. The town's modern prosperity is largely a result of the immense success of Brunello, which was pioneered by local farmers in the 19th century.

Top Attractions:

• The imposing 14th-century Fortezza di Montalcino dominates the town, offering spectacular views of the Val d'Orcia from its ramparts.
• For a spiritual and artistic experience, visit the beautiful Romanesque Abbazia di Sant'Antimo, nestled in a peaceful valley nearby.
• The UNESCO World Heritage site of Val d'Orcia, with its picturesque rolling hills and cypress trees, surrounds the town, providing endless opportunities for scenic drives and photography.
• The Museo Civico e Diocesano d'Arte Sacra offers a collection of religious art that details the town's history.

High-End Hotels:

• Castello di Velona Resort: a 5-star hotel and thermal spa located in a stunning medieval castle, offering panoramic views.
• Castel Monastero Resort: an upscale resort housed in a former monastery, featuring fine dining and a tranquil atmosphere.
• Rosewood Castiglion del Bosco: this luxury resort, situated on an expansive estate, offers a high-end stay with a wine bar and outdoor pool.

High-End Restaurants:

• Boccon Divino: this restaurant provides artfully presented dishes and sweeping views from its terrace.
• La Taverna: located within the Castello Banfi estate, this restaurant offers exquisite Tuscan cuisine paired with its world-renowned wines.
• Alle Loggie di Piazza: this highly-rated restaurant on the central square is perfect for a refined dining experience.

Elite Vineyards and Wines:

• Biondi-Santi Tenuta Greppo is a pioneer of Brunello, producing sought-after vintages. 
• Castello Banfi is a large estate known for its consistent quality and stunning location. 
• Casanova di Neri is a smaller estate that consistently receives top ratings for its Brunellos.
• The legendary Soldera Case Basse produces some of the most powerful and long-lived Brunellos. The most elite wines are the Brunello di Montalcino Riserva and the top-tier single-vineyard bottlings from these producers. 

Montepulciano: The Renaissance Hill Town

Montepulciano is a magnificent medieval and Renaissance hill town with roots tracing back to the Etruscans and Romans. During the Renaissance, it experienced a period of great artistic and cultural flourishing, attracting renowned architects who built magnificent palaces and churches. After losing its strategic importance in the mid-16th century, its significance waned until the unification of Italy. Today, its historic elegance and acclaimed Vino Nobile have re-established it as a top destination.

Top Attractions:

• The heart of the town is the grand Piazza Grande, surrounded by architectural gems like the Palazzo Comunale and the Duomo.
• The impressive Tempio di San Biagio, located just outside the town walls, is a masterpiece of Renaissance architecture. For a unique experience, explore the ancient subterranean cellars and tunnels beneath the town's historic buildings.
• Climbing the tower of the Palazzo Comunale offers spectacular panoramic views of the town and surrounding countryside.

High-End Hotels:

• Villa Cicolina: this historic villa provides classic Tuscan hospitality and scenic views.
• Precise Tale Poggio Alla Sala offers an upscale accommodation experience with a natural spa.
• Palazzo Carletti: stay in a beautifully restored historic palace with elegant interiors and frescoes.

High-End Restaurants:

• Le Logge del Vignola offers refined cuisine and a romantic dining experience.
• L'Altro Cantuccio Ristorante provides inventive Tuscan dishes in a rustic-chic setting.
• La Vineria di Montepulciano: A cozy wine bar that serves excellent charcuterie boards and small plates in an old-world ambiance.

Elite Vineyards and Wines:

• Avignonesi is a pioneer in biodynamic winemaking and produces some of the region's most respected Vino Nobile. 
• Poliziano is a large estate known for its consistently high-quality wines. 
• Contucci, one of the oldest wineries in Montepulciano, has historic cellars directly beneath the town. 
• Boscarelli is a family-run winery that produces traditional and elegant Vino Nobile.

Recommended Day Experiences:

San Gimignano: The City of Fine Towers

Known as the "Manhattan of the Middle Ages" for its iconic towers, San Gimignano is a medieval walled town with Etruscan origins. During its peak in the 13th and 14th centuries, rival patrician families competed to build the tallest towers as symbols of their wealth and power. The town flourished as a relay point on the Via Francigena, the pilgrimage route to Rome. Though only 14 of the original 72 towers remain, the town has perfectly preserved its feudal appearance and is a UNESCO World Heritage site.

Top Attractions:

• Climbing the Torre Grossa, the tallest of the remaining towers, offers the best panoramic views of the town and the surrounding countryside.
• The central Piazza della Cisterna, with its medieval buildings and central cistern, is a picturesque setting.
• The Duomo di San Gimignano, or Collegiate Church, is a must-see for its spectacular frescoes.
• The Historic Centre itself is an attraction, with its narrow streets, ancient architecture, and numerous shops and restaurants.

High-End Hotels:

• Hotel La Collegiata: a romantic and elegant stay in a former convent.
• Hotel Casolare Le Terre Rosse offers excellent facilities and great value just outside the historic center.
• Castello Di Casole: a luxurious resort set within a historic castle and estate.

High-End Restaurants:

• Cum Quibus - Ristorante Toscano provides high-end, contemporary Italian food.
• Zafferano by Casanova di Pescille: known for excellent dining with views of the countryside.
• La Mandragola: a classic restaurant offering a fine dining experience.

Elite Vineyards and Wines:

• San Gimignano is celebrated for its Vernaccia di San Gimignano, one of Italy's most prestigious white wines. Tenuta Guardastelle is a boutique, organic winery known for its highly-rated Vernaccia and hospitable atmosphere.
• Podere La Marronaia is another highly regarded organic and biodynamic winery with lovely views and well-made Vernaccia.
• Fattoria Il Piano is also praised for its high-quality and affordable Vernaccia and Chianti.

Recommended Day Experiences:

• Wine and Food Tasting in an Organic Family Winery
• Tuscany Wine Experience and 3 Wineries Tour with Lunch

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