Embark on a Siena Chianti and Wine Tasting captivating journey from Florence into the heart of Tuscany, where time seems to stand still amidst rolling hills and historic walled towns. This full-day tour offers a perfect escape from the city, allowing you to immerse yourself in the rich history, stunning landscapes, and culinary delights of the region. From the soaring towers of San Gimignano to the magnificent Duomo of Siena, this experience is a true testament to the enduring beauty of medieval Italy.

Your adventure begins with a comfortable bus ride, providing a panoramic view of the iconic Tuscan countryside—a tapestry of sun-drenched vineyards, silver olive groves, and golden wheat fields. An experienced live tour guide will accompany you, sharing fascinating stories and historical facts about the places you’ll visit, making the journey as enriching as the destinations themselves.

Your first destination is the enchanting walled town of San Gimignano, a UNESCO World Heritage site often referred to as the “Medieval Manhattan” due to its remarkably preserved towers. As you step inside its ancient walls, you’ll feel transported back in time. The town’s narrow, winding streets are filled with artisan shops, charming cafes, and hidden courtyards. You’ll have approximately two hours of free time to explore this gem at your own pace. Climb to the top of one of its few remaining towers for a breathtaking view, discover local art in its numerous galleries, or simply relax in the central square, Piazza della Cisterna, and soak in the historic atmosphere.

After exploring San Gimignano, the tour takes you deeper into the Tuscan hills for a special experience: a visit to a traditional Chianti winery. Here, you will be treated to a delightful three-course lunch, featuring authentic local dishes. The meal is perfectly complemented by a guided wine tasting, where you’ll have the chance to sample the famous Chianti wines, renowned for their fruity notes and elegant character. This is more than just a meal; it’s a sensory experience that connects you directly with the land and the passion of Tuscan winemakers.

Following lunch, the tour continues to the historic hamlet of Monteriggioni. This small, perfectly preserved fortress town, with its formidable walls and towers, is a sight to behold. A short stop here allows you to walk through its peaceful main square and imagine life in a medieval stronghold. The village’s authenticity and charm make it a memorable part of the tour, a quiet interlude before the final, grand destination.

The day culminates in Siena, a city of breathtaking beauty and a UNESCO World Heritage site. As you stroll through its historic center, you’ll be captivated by its medieval streets and the stunning Gothic architecture. The highlight of Siena is the iconic Piazza del Campo, the shell-shaped main square where the famous Palio horse race is held twice a year. You can also visit the magnificent Basilica of San Domenico, and for those who choose the optional upgrade, the awe-inspiring Siena Cathedral (Duomo), a masterpiece of Italian Gothic architecture. With its intricate facade, stunning marble floors, and priceless art, the cathedral is an absolute must-see. You’ll have free time to explore the city’s highlights, from its bustling squares to its tranquil back alleys.

In conclusion, this tour to Siena and San Gimignano is an exceptional way to discover the heart of Tuscany’s medieval past. It combines the freedom to explore at your own pace with the convenience of organized transport and expert guidance. From the iconic towers of San Gimignano to the artistic treasures of Siena and the delicious flavors of Chianti, this journey is a rich tapestry of culture, history, and beauty. While the tour requires some walking and is not suitable for wheelchair users, the reward is a day filled with unforgettable memories of one of Italy’s most beautiful regions.

Highlights of Siena Chianti and Wine Tasting Lunch

• Visit two UNESCO World Heritage sites
• Tour the beautiful Siena Cathedral, led by a local guide
• Enjoy wonderful views of Tuscan rolling hills and Chianti countryside
• Stop at a Chianti winery for lunch and a guided tasting of three different wines

• Transportation by air-conditioned bus
• Multilingual tour escort on board
• Lunch with wine tasting
• Local guide in Siena (if option selected)
• Siena Cathedral entry ticket (if option selected)
• Siena Cathedral guided visit (if option selected)

• Hotel pickup and drop-off

.An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station. It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the Tour, nor to have a refund or reschedule the tour.

Not suitable for

• Wheelchair users

What to bring

• Comfortable shoes

Not allowed

• Pets

Know before you go

• This tour involves uphill and downhill walking routes in hilltop villages. Therefore we regret to inform you that it is not suitable for people with wheelchairs or with impaired mobility.
• Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation
• Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.