Tuscany’s medieval gems shine bright on this full-day tour from Florence. Explore the historic towns of Siena, Monteriggioni, and San Gimignano, each brimming with captivating architecture and enchanting stories. Marvel at Siena’s magnificent cathedral and the iconic Piazza del Campo, then savor the panoramic vistas from San Gimignano’s towering medieval structures. In between, discover the charm of Monteriggioni’s walled town. But the highlights don’t end there – a Tuscan lunch and wine tasting at a picturesque vineyard promise to delight the senses. With a seamless blend of culture, history, and culinary delights, this tour offers a true taste of the Tuscan experience.
Key Points
- A full-day tour from Florence to the historic Tuscan towns of Siena, Monteriggioni, and San Gimignano, including a lunch and wine tasting experience.
- Highlights of the tour include visits to the Leaning Tower of Pisa, the medieval towers of San Gimignano, and the Palio horse race venue in Siena.
- The tour includes transportation in a private minivan, with an English-speaking driver, and the option to customize the itinerary upon request.
- The tour features a stop for a traditional Tuscan lunch and guided wine tasting at a countryside estate, but is not accessible for wheelchair users.
- The tour provides an opportunity to explore the UNESCO World Heritage sites of Pisa, San Gimignano, and Siena, as well as the well-preserved medieval town of Monteriggioni.
Tour Overview

This full-day tour takes visitors from Florence to the historic Tuscan towns of Siena, Monteriggioni, and San Gimignano.
Operated by ItalyBestExcursions, the tour includes hotel pickup and drop-off in a private, air-conditioned minivan that can accommodate up to eight passengers.
Passengers have the option to customize the tour if requested at booking.
The excursion covers key highlights such as the Leaning Tower of Pisa, the medieval towers of San Gimignano, and the Palio horse race venue in Siena.
Lunch and wine tasting at a countryside estate are also included, with soft drinks for underage guests.
The tour is suitable for most travelers, though it’s not wheelchair accessible.
You can also read our reviews of more tours and experiences in Florence
Highlights of the Itinerary
The tour first visits the iconic Leaning Tower of Pisa and other highlights at the Piazza dei Miracoli, including the cathedral, baptistery, and cemetery.
Next, it explores the medieval town of San Gimignano, a UNESCO World Heritage Site known for its Gothic and Romanesque towers.
In Siena, the group will discover the city famous for the Palio horse race, visiting the town cathedral and the Piazza del Campo.
Along the way, they’ll pass by the medieval town of Monteriggioni.
The tour also includes a light lunch and wine tasting at Tenuta Torciano in the Tuscan countryside.
Pisa and Piazza Dei Miracoli

The tour begins at the iconic Leaning Tower of Pisa, one of Italy’s most famous landmarks.
Visitors will have the opportunity to explore the remarkable Piazza dei Miracoli, home to the cathedral, baptistery, and cemetery.
The Leaning Tower’s distinctive tilt is the result of its poor foundation and soft ground, which caused it to gradually lean over time. Guests can opt to climb the 294 steps to the top of the tower, offering stunning panoramic views of the city.
The piazza’s architectural masterpieces, blending Gothic, Romanesque, and Renaissance styles, create a breathtaking ensemble and a UNESCO World Heritage Site.
Exploring San Gimignano

After leaving the iconic Pisa, the tour then ventures to the medieval town of San Gimignano.
This UNESCO World Heritage Site is renowned for its impressive Gothic and Romanesque towers that dot the skyline. Visitors can explore the charming streets, discovering quaint shops, cafes, and historic churches.
The group will have time to wander at their own pace, soaking up the town’s unique atmosphere. San Gimignano’s strategic hilltop location provides panoramic views of the surrounding Tuscan countryside, making it a highlight of the day’s itinerary.
With its well-preserved architecture and captivating history, this Tuscan gem offers a glimpse into a bygone era.
Discovering Siena

Next, the tour heads to the historic city of Siena, known for its captivating Palio horse race.
Visitors will discover the city’s renowned landmarks, including:
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The Siena Cathedral, a magnificent Gothic cathedral featuring intricate marble striations and a bell tower with a distinctive spire.
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Piazza del Campo, the famous shell-shaped town square where the Palio race takes place every July and August.
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The Palazzo Pubblico, a towering civic building housing the Museo Civico and its stunning frescoes.
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The Basilica of San Domenico, a 13th-century church known for its renowned art collection and the relics of Saint Catherine of Siena.
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Monteriggioni Medieval Town

As the tour continues, visitors are treated to a picturesque drive through the Tuscan countryside towards the medieval town of Monteriggioni. This well-preserved 13th-century walled town sits atop a hill, its defensive walls and towers still intact. Strolling through the quaint streets, visitors can imagine life in the Middle Ages, with each building and cobblestone evoking a sense of history. The town’s strategic location made it a crucial stronghold, and today it remains a testament to the region’s rich heritage.
| Feature | Description |
|---|---|
| Walls | Fully intact 13th-century defensive walls |
| Towers | 14 towers still standing, offering panoramic views |
| Architecture | Romanesque and Gothic styles throughout the town |
| History | Crucial medieval stronghold, now a preserved landmark |
Lunch and Wine Tasting

Following the drive through the picturesque Tuscan countryside, the tour takes a break for a light lunch and wine tasting at Tenuta Torciano.
The minimum drinking age for the wine tasting is 18, but soft drinks are available for younger guests. The lunch and tasting offer a chance to sample the region’s renowned wines and local cuisine.
The experience includes:
- A light, traditional Tuscan lunch
- A guided wine tasting of the estate’s finest varietals
- An opportunity to purchase wines to take home
- Stunning views of the surrounding vineyards and rolling hills.
Transportation and Accessibility

The tour provides air-conditioned, fully insured transportation in a private vehicle with a professional English-speaking driver.
Shared tours may involve 2-3 stops for passenger pickup and dropoff, which could result in arrival times varying by 15-30 minutes.
The vehicle isn’t wheelchair accessible, but suitable for most travelers. Infant seats are available upon request.
While tipping isn’t included, it’s appreciated by the driver for their excellent service in ensuring a smooth and comfortable journey through the scenic Tuscan countryside.
Frequently Asked Questions
What Is the Cancellation Policy for This Tour?
The cancellation policy for this tour is non-refundable, meaning customers can’t get their money back if they cancel their booking. This is a standard policy for many tours and activities.
Are Any Discounts Available for Children or Seniors?
The tour does not offer any discounted prices for children or seniors. However, soft drinks are available for younger guests during the wine tasting portion of the tour.
Can the Pickup/Dropoff Location Be Customized?
The pickup and dropoff locations for this tour can be customized upon request at the time of booking. The tour operator offers private tours, allowing for a more personalized experience.
What Is the Maximum Group Size for the Private Tour Option?
The private tour option allows for customizable pickup and dropoff locations and has room for up to 8 passengers. Guests can request customizations at the time of booking with the tour operator, ItalyBestExcursions.
Are There Any Dietary Restrictions Accommodated for the Lunch?
The tour accommodates dietary restrictions for the lunch, including vegetarian, vegan, and gluten-free options. Guests must notify the tour operator of any dietary needs at the time of booking.
Siena Monteriggioni San Gimignano With Lunch&Winetasting Fullday From Florence
Sum Up
This full-day tour from Florence offers a captivating exploration of Tuscany’s historic gems. Visitors will marvel at the stunning cathedrals and medieval towers, savor a delightful Tuscan lunch and wine tasting, and enjoy the region’s rich culture and picturesque landscapes. It’s the perfect blend of history, gastronomy, and scenic beauty, making it an unforgettable experience for anyone seeking to discover the charm of Tuscany.






















