From Siena: San Gimignano, Chianti, and Montalcino Day Trip

Exploring the charming towns of San Gimignano, Chianti, and Montalcino from Siena is a must-do for any traveler seeking to enjoy Tuscany’s rich history and renowned wine culture. This small group day trip promises a captivating journey through stunning landscapes, with opportunities to discover medieval architecture, indulge in tastings of the region’s finest wines, and savor the local cuisine. Whether you’re a seasoned oenophile or simply seeking to uncover the essence of this remarkable corner of Italy, this tour offers an unforgettable experience that will leave you eager to delve deeper into the wonders of Tuscany.

Key Points

• A day trip from Siena exploring historic sites and renowned wine regions, including San Gimignano, Chianti, and Montalcino.
• Tour includes transportation, wine tastings, and free time to wander the charming towns.
• Highlights encompass UNESCO-listed sites, medieval towers, and opportunities to sample Vernaccia, Chianti, and Brunello wines.
• Small group tour limited to 15 participants, available in multiple languages.
• Flexible cancellation policy and hotel pickup/drop-off for convenience.

You can check availability for your dates here:

Tour Overview and Pricing

This day trip from Siena takes travelers to explore the historic sites and renowned wine regions of San Gimignano, Chianti, and Montalcino.

The price starts from $152.33 per person for this 11-hour small group tour, limited to 15 participants. The tour is available in English, Spanish, and Italian.

This 11-hour small group tour, limited to 15 participants, is available in English, Spanish, and Italian for $152.33 per person.

Highlights include visiting the UNESCO-listed San Gimignano, touring a Chianti winery, and discovering the UNESCO-recognized Val d’Orcia and Montalcino, famous for its Brunello wines.

Tastings at the Chianti and Montalcino wineries are included, as is transportation from Siena in an air-conditioned vehicle with an expert multilingual guide.

Itinerary Highlights

The day trip from Siena takes visitors to explore several renowned UNESCO World Heritage sites and wine regions.

The itinerary highlights include:

• Visiting San Gimignano, a medieval town famous for its iconic skyline of towering stone Gothic towers and renowned for its production of Vernaccia wine.

• Exploring the picturesque Chianti wine region, with a winery tour and tastings of its signature Chianti wines.

• Discovering the Val d’Orcia, a stunning landscape designated as a UNESCO World Heritage site in 2004.

• Visiting Montalcino, home to the esteemed Brunello vineyards and renowned for its exceptional red wines.

• Enjoying free time to wander the charming streets of San Gimignano and Montalcino.

Exploring San Gimignano

San Gimignano is a captivating medieval town that beckons visitors with its iconic skyline of towering stone Gothic towers.

Wandering its winding streets, travelers can marvel at the remarkably well-preserved historic center, a UNESCO World Heritage site.

The town’s most striking features are its 14 medieval towers, some reaching 200 feet high. Visitors can climb to the top of the 13th-century Torre Grossa for panoramic views of the surrounding countryside.

San Gimignano is also known for its Vernaccia di San Gimignano, a crisp white wine that pairs perfectly with the local cuisine.

Discovering the Chianti Wine Region

After exploring the medieval charms of San Gimignano, the tour continues into the renowned Chianti wine region.

The group visits a local winery to indulge in a tasting of four distinct wines, including a Chianti Riserva and a Toscana Rosso. Paired with the wine are local salami, olive oils, and balsamic vinegars, providing a complete sensory experience.

The winery tour offers insights into the region’s winemaking traditions and the unique terroir that gives Chianti wines their signature flavor profile.

With the Tuscan countryside as a stunning backdrop, this stop is a highlight of the day’s adventures.

• Tasting of 4 Chianti wines

• Pairing with local salami, olive oils, and balsamic vinegars

• Winery tour showcasing the region’s winemaking heritage

• Opportunity to learn about the Chianti terroir

• Picturesque Tuscan scenery as a breathtaking setting

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Visiting Val D’orcia and Montalcino

Next, the tour ventures into the breathtaking Val d’Orcia region, a UNESCO World Heritage site since 2004.

This idyllic countryside is known for its rolling hills, cypress trees, and medieval towns.

The highlight is a visit to Montalcino, home to the prestigious Brunello di Montalcino wines. Participants sample a selection of these full-bodied reds, paired with local cured meats and cheeses, at a renowned wine cellar.

With free time to explore Montalcino’s historic center, visitors can admire the 14th-century fortress and browse quaint shops before returning to Siena, memories of Tuscany’s beauty and flavors in tow.

Wine Tasting Experiences

As participants venture into the Chianti wine region, they’ve the opportunity to partake in a winery tour and wine tastings.

During this experience, they can sample a selection of 4 wines, including:

• Spumante Cuvée

• Chianti Riserva

• Toscana Rosso

• Spumante Rosé

These wines are accompanied by local salami, olive oils (Frantoiano Biologico, White Truffle, Chili Pepper), and balsamic vinegars.

Later, the group visits a Montalcino wine cellar to sample 4 more wines, such as IGT Toscana Rosso or Toscana Bianco, DOC Rosso di Montalcino, and DOCG Brunello di Montalcino, paired with bruschetta, cured meats, and cheeses.

Tour Inclusions and Logistics

The day trip from Siena includes several helpful inclusions and logistical details.

Departing from Siena, guests travel in an air-conditioned minivan or minibus with an expert multilingual tour leader. Pickup and drop-off at hotels are provided for convenience.

Visitors enjoy free time to explore the charming towns of San Gimignano and Montalcino. The tour also includes wine tastings at a Chianti winery and a Montalcino wine cellar.

While lunch is at one’s own expense, an optional lunch at a Chianti winery is available. With free cancellation up to 24 hours in advance, this day trip offers an immersive Tuscan experience.

Important Information and Recommendations

This day trip offers free cancellation up to 24 hours in advance, providing flexibility for travelers.

To ensure a comfortable experience, visitors are advised to wear sturdy, walking-friendly shoes as the tour involves moderate walking. Plus, checking the weather forecast and dressing appropriately is recommended.

Wear sturdy shoes for moderate walking and check the weather to dress appropriately for a comfortable experience.

Don’t forget to bring a camera to capture the stunning Tuscan landscapes.

While tasting fees are included, lunch is at the traveler’s own expense, allowing for personalized dining options.

• Wear comfortable shoes for moderate walking

• Check weather and dress accordingly

• Bring a camera to capture Tuscan scenery

• Tasting fees included, lunch at own expense

• Free cancellation up to 24 hours in advance

The Sum Up

This captivating day trip from Siena offers an immersive experience in Tuscany’s enchanting towns and renowned wine regions. Travelers will explore the medieval charm of San Gimignano, indulge in Chianti wine tastings, and savor the renowned Brunello wines of Montalcino, all while enjoying the region’s stunning landscapes. With expert guides and comfortable transportation, this small-group tour promises an unforgettable journey through Tuscany’s rich cultural and gastronomic heritage.

You can check availability for your dates here: