Private Best of Tuscany Hill Towns Tour with lunch from Florence

Imagine cruising through rolling Tuscan landscapes in a comfy private Mercedes minivan, with an expert guide sharing stories about medieval towers, legendary horse races, and world-class wines. That’s exactly what you get with this Private Best of Tuscany Hill Towns Tour with Lunch from Florence. For around $663 per person, you’ll spend about nine hours exploring two of Italy’s most picture-perfect towns: Siena and San Gimignano. Plus, you’ll enjoy a typical Tuscan lunch paired with wine tastings at a carefully selected vineyard.

What we really love about this tour is the personalized attention that comes with a private guide and driver, making the experience both intimate and flexible. It’s not a rushed bus trip—this is about savoring Tuscany at a relaxed pace, soaking in the views, and learning from locals. Another highlight is the scenic drive through countryside, offering countless photo opportunities and a true sense of rural Italy.

One possible consideration is the price point—at over $660, it’s an investment, but one that many feel is justified given the inclusions and comfort. You should be ready for a full day out, with some walking involved in town centers, and prepare for a busy schedule if you want to maximize your experience.

This tour suits travelers who appreciate a mix of culture, history, and wine, and who prefer a more tailored experience than a large group excursion. If you’re keen on personalized service, authentic small-town charm, and delicious food and wine, this trip is likely to be just right.

Key Points

• Private & personalized: Smaller group, more flexible, and guided by an expert driver-guide.
• Cultural highlights: Visit Siena’s famous Palio di Siena square and San Gimignano’s medieval towers.
• Tasting experiences: Includes visits to a winery with wine tasting and a traditional Tuscan lunch.
• Comfortable transport: Travel in a luxury, air-conditioned Mercedes vehicle.
• Scenic routes: Enjoy the beauty of Tuscany’s countryside with plenty of photo stops.
• Value for money: The tour includes entrance-free visits, a sumptuous lunch, and wine tastings, all in one package.

Starting Out: A Comfortable Departure from Florence

The tour begins conveniently in the heart of Florence, at Piazza della Repubblica. Expect to meet your driver-escort early—around 8 am—which gives you plenty of time to settle in and prepare for a day filled with scenic drives and historical sights. The vehicle is a luxurious Mercedes with air conditioning, ensuring a comfortable ride through Tuscany’s curvy roads and picturesque landscapes.

The small group size means you won’t feel lost in a crowd. Several reviews praise the friendly, knowledgeable guides like Giuliano, Lorenzo, or Fabrizio, who not only drive but also share fascinating stories about the towns and the region’s culture.

The First Stop: Siena’s Enchanting Historic Center

Your first major destination is Siena, famed for its Palio di Siena, an annual horse race that electrifies the town. While the tour doesn’t specify a certain time for the Palio, you’ll get plenty of time to walk around Siena’s main square, Piazza del Campo. Here, you can appreciate its distinctive shell shape and medieval architecture, with old towers and charming cafes lining the square.

A highlight is the local guide in Siena, who often shows visitors the city’s lesser-known nooks and crannies—places you might miss alone. Expect to learn about Siena’s medieval history and its unique Gothic architecture, with some reviews praising guides who “showed us a personal side of the city.”

Lunch and Wine Tasting: A True Taste of Tuscany

After Siena, the journey continues with a Tuscan lunch—a shared platter of cheeses, meats, and local specialties at a winery or a dedicated restaurant. Many reviews mention the generous wine servings, sometimes nearly a full glass or more, which can be a delightful surprise but also something to consider if you prefer lighter tastings.

The winery visit is a major part of the experience, with wine tasting included. The vineyards are described as hospitable, with growers eager to share their craft. While some guests mention the wines may not be to everyone’s palate, the overall sentiment is positive, especially if you enjoy sampling local varieties in beautiful settings. One reviewer noted that “the scenery was remarkable,” and the wines were reasonably priced.

The Medieval Charm of San Gimignano

Next, you’ll head to San Gimignano, often called the Medieval Manhattan because of its iconic towers. The town’s skyline is instantly recognizable, and it’s easy to see why visitors fall in love with its charming streets and panoramic views. You’ll have about an hour and a half here, giving enough time to climb Torre Grossa for sweeping vistas, visit the cathedral, or simply enjoy a gelato in Cistern Square.

Many guests describe San Gimignano as “beautiful” and “picturesque,” with the towers offering an authentic glimpse into medieval Italy’s history of wealth and power. Some reviews highlight the stunning scenery and the medieval architecture as the highlights of this stop.

Scenic Return and Final Reflections

As the day winds down, the tour takes you back to Florence through scenic countryside. Along the way, your guide might point out additional sights or share stories about the region’s agriculture, pottery, and local traditions. The entire experience wraps up around 5 pm, back at the starting point.

What Makes This Tour Stand Out?

Beyond the obvious charm of the towns, many reviewers praise the expert guides and drivers. For example, one reviewer emphasized that “our guide Yaris was the best—knowledgeable and giving us the experience of a lifetime,” which speaks to the quality of personalized attention you can expect.

You’ll also appreciate the value that comes with the inclusions: entrance-free visits, a local lunch, and wine tastings—all in one package. For many, the comfortable transportation and small-group setting make a big difference in enjoying the day without feeling rushed or crowded.

Possible Drawbacks to Consider

While most reviews are glowing, a few mention the size of the wine servings—which can be quite generous—and the price might seem steep for some travelers. Plus, the itinerary order may vary, and there’s a lot to pack into one day, so if you prefer a slower pace or more time in each town, this might not be ideal.

This experience is perfect for travelers who want a personalized, hassle-free day exploring Tuscany’s most iconic hill towns. It’s suited for those who value expert guidance, comfortable transportation, and culinary delights in a small-group setting. If you’re eager to enjoy wine tastings in beautiful vineyards, see Siena’s medieval splendor, and take in San Gimignano’s skyline, this tour hits all the right notes.

It’s also ideal for visitors who might feel overwhelmed planning their own day—this tour provides a well-organized itinerary with a local touch. However, if you prefer a very leisurely pace or want to explore each town independently, consider whether the busy schedule matches your travel style.

This private tour offers a comprehensive taste of Tuscany’s best hill towns, combined with delicious food and wine and personalized service. The expert guides and luxurious transport elevate the experience beyond just sightseeing, creating a memorable day that balances education, relaxation, and indulgence.

For those who want an authentic, well-curated experience without the chaos of larger tours, this is a strong choice. The reviews confirm that many guests leave feeling that their day was “one of the best experiences in Italy,” and with good reason.

However, the cost might be a consideration for budget travelers, and the full schedule requires a bit of energy. If you’re a history lover, a wine enthusiast, or simply want to see Tuscany in style and comfort, this tour is likely to deliver more than you expect.

What towns does the tour visit?
You’ll visit Siena and San Gimignano, two of Tuscany’s most famous medieval towns. The order may vary.

How long does the tour last?
The entire experience is about 9 hours, typically starting at 8 am and returning around 5 pm.

Is the transportation comfortable?
Yes, you’ll travel in a private Mercedes or similar vehicle, equipped with air conditioning, ensuring a smooth and comfortable ride.

What’s included in the tour?
The package includes visits to Siena and San Gimignano, a winery tour with wine tasting, a traditional Tuscan lunch, and the services of an expert English-speaking driver-guide.

Can children participate?
Yes, most travelers can participate, but children must be accompanied by an adult. All passengers pay the same rate regardless of age.

Is this tour suitable for photography?
Absolutely. You’ll have opportunities to take photos of scenic countryside, town views, and landmarks such as Torre Grossa. Some reviews mention that the timing might be tight for extensive photography.

What should I wear?
Dress comfortably and appropriately for the weather, as the tour operates in all conditions. Comfortable shoes are recommended for walking in towns.

How far in advance should I book?
Most travelers book about 125 days ahead, especially during peak seasons, to secure availability.

What happens if I need to cancel?
You can cancel for free up to 24 hours before the tour. Cancellations made less than 24 hours in advance are non-refundable.

This detailed look at the Private Best of Tuscany Hill Towns Tour reveals a well-rounded, authentic experience suited for travelers seeking comfort, personalization, and a taste of Tuscany’s highlights. It offers a chance to enjoy Italy’s countryside, history, and culture without the stress of planning every detail yourself—perfect for those wanting to indulge in a memorable day out.