Tuscany Day Trip: San Gimignano, Siena, Chianti - Lunch & Wine
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Overview
Discover Tuscany's magic on the San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting. This full-day adventure takes travelers to the heart of Italy's most beautiful region. Explore medieval towns, taste delicious wines, and enjoy a traditional Tuscan lunch.
What to Expect: The journey begins in San Gimignano, known for its stunning towers and walls. Visitors will walk through Piazza della Cisterna and marvel at the views from the old Walls of San Gimignano. The tour then moves to Monteriggioni Hamlet (*). Next, the tour goes to a Chianti winery for a Tuscan lunch with wine tasting. The final stop is Siena, where a local guide shows the historic center, including Piazza Salimbeni and the famous Piazza del Campo. Depending on the selected option, the guided tour may include Siena Cathedral and Piccolomini Library.
Included is transport by air-conditioned coach, a 3-course Tuscan lunch, and wine tasting. Guests will sample three Chianti wines, olive oil, and “vin santo.” A licensed tour leader provides commentary. The order of visits may change. Please note that the Shared Round Transport option does not include the Siena Guided Visit or Cathedral admission. From November to March, the tour excludes the stop at Monteriggioni and arrives back in Florence approximately 30 minutes earlier.




Highlights
Explore San Gimignano: See the famous towers of this medieval town and walk its historic streets.
Discover Siena's History: Visit the Piazza del Campo and learn about Siena's rich culture with a local guide.
Taste Chianti Wines: Enjoy a tasting of three different Chianti wines at a local winery.
Enjoy a Tuscan Lunch: Savor a traditional 3-course Tuscan lunch at a Chianti Winery.
Sentiment Analysis
Customers generally enjoyed the tour, praising the scenery, food, and guides. However, some felt rushed and wanted more time at each stop.

Customers loved seeing beautiful places in Tuscany.
They enjoyed the wine tasting and lunch.
The guides were very good and told interesting facts.
Many people thought it was a great way to spend a day.
Some customers felt that the tour was rushed.
Some customers felt that there was not enough time in each location.
The Journey
San Gimignano
Step back in time in San Gimignano, a UNESCO World Heritage site celebrated for its remarkably preserved medieval architecture. This hilltop town, famed for its iconic towers that once symbolized the wealth and power of its leading families, offers a captivating glimpse into the past. Wander through its historic center, adorned with stunning frescoes and invaluable works of art, and immerse yourself in the enchanting atmosphere that has remained intact through the centuries. Two hours of free time allows for a fascinating self-discovery.
Piazza della Cisterna
Discover the heart of San Gimignano at Piazza della Cisterna, a charming triangular-shaped medieval square paved with ancient stones. This central gathering place is named after the historic cistern at its center, once the town's primary water source. Surrounded by well-preserved medieval towers and historic buildings, the square exudes a timeless atmosphere, offering visitors a captivating focal point within this UNESCO World Heritage site.
Walls of San Gimignano
Experience the history and beauty of San Gimignano by walking along its well-preserved 13th-century walls, known as the "Mura." Originally built for defense and as a symbol of civic pride, these walls now offer a scenic promenade with breathtaking panoramic views of the town, its iconic towers, and the picturesque Tuscan countryside. Capture stunning vistas and immerse yourself in the medieval ambiance of this enchanting town.
Monteriggioni
Venture just a short distance from San Gimignano to the charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous and remarkably intact walls. Explore within these ancient fortifications and imagine life in this strategic stronghold. (*Note: From November to March, the tour may not include a stop at Monteriggioni, resulting in an earlier return to Florence.)
Chianti Winery
Indulge in the flavors of Tuscany at a cozy winery nestled in the rolling hills of Chianti. Relax and immerse yourself in the world of Chianti wine and typical local products with a tasting of three fine wines and balsamic vinegar. Savor a delicious Chianti-style lunch, a three-course meal featuring "zero food miles" products, concluding with the traditional "cantucci e vin santo" dessert, a perfect pairing of almond biscotti and sweet dessert wine.
Siena Historic Center
Discover the historical heart of Siena, where a professional local guide will lead you through its narrow medieval streets, lined with splendid palaces and historic shops. Stroll past architectural gems and hidden corners, gaining insights into the city's rich history and vibrant culture. Prepare to be enchanted by the unique atmosphere of this captivating city.
Piazza Salimbeni
Begin your Siena adventure at Piazza Salimbeni, home to the Palazzo Salimbeni, the historical headquarters of the world's oldest bank. Marvel at the architecture and historical significance of this ancient palace, a testament to Siena's enduring legacy in the world of finance.
Piazza del Campo
Experience the grandeur of Piazza del Campo, Siena's main public space and the site of the famous Palio horse race. Admire the Palazzo Pubblico (Town Hall), the square's focal point, and soak in the vibrant atmosphere of this iconic location. Its unique shell shape and historic significance make it a must-see destination.
Siena Cathedral
Behold the spectacular Siena Cathedral, a masterpiece of 12th-century architecture. Admire its magnificent facade and the splendor of its polychrome marbles, showcasing the artistry of the era. (Inside visit available only if the cathedral entrance option is selected). Its elaborate design and artistic treasures make it a highlight of any visit to Siena.
Piccolomini Library
Enter the Piccolomini Library (only with cathedral entrance option), a Renaissance gem housed within the Duomo di Siena. Admire the vibrant frescoes by Pinturicchio, commissioned by Pope Pius III, which depict scenes from his life. This cultural and artistic treasure within the Siena Cathedral offers a glimpse into the opulence and artistry of the Renaissance era.
Chiantigiana Road
Embark on a scenic drive along the Chiantigiana road, a legendary route that winds through the picturesque Chianti region. Traverse rolling hills adorned with vineyards, olive groves, and charming villages. Encounter classic Tuscan landscapes, medieval castles, and renowned wineries producing the world-famous Chianti wine. Enjoy a delightful blend of cultural richness, culinary delights, and breathtaking views, capturing the essence of the authentic Tuscan experience.
Know Before You Go
This tour includes transport by G.T. air-conditioned coach and a 3-course typical Tuscan lunch in a Chianti Winery. It also includes a tasting of three different Chianti Wines, extra virgin olive oil & “vin santo”. If the option is selected, a Siena Cathedral interior Guided Visit including the entrance fee is included. The tour has a Licensed Tour Leader with live commentary on board. From April to October, the visit in Siena is monolingual. The Shared Round Transport option does NOT include the Siena Guided Visit or Cathedral admission. From November to March, the itinerary does not include the stop at Monteriggioni.
Hot Tip
Some customers suggest wearing comfortable shoes, as there is a lot of walking. Also, they advise bringing a water bottle to stay hydrated, especially during the summer months.