Private Best of Tuscany Hill Towns Tour with lunch from Florence

Tuscany’s rolling hills and medieval towns have long captivated travelers, and this private tour offers a thoughtfully curated way to enjoy some of its most famous spots—Siena and San Gimignano—without the hassle of driving or navigating public transport. While it’s priced at around $662.98 per person, the experience is designed to blend comfort, personalized attention, and authentic Italian charm.

What truly sets this tour apart are the knowledgeable guides, stunning scenic routes, and the opportunity to sample local wines paired with a traditional Tuscan lunch. However, as with any guided experience, some may find the schedule tight, especially if you’re hoping for extensive time in each town or a more casual pace.

This tour is ideal for travelers who want a stress-free, comprehensive day out with a personal touch, especially if they value expert insights and local flavor over self-guided exploration.

Key Points

• Private Tour Experience: Enjoy a personalized, small-group feel with an expert driver-guide.
• Two Iconic Hill Towns: Visit Siena and San Gimignano, each with a unique medieval charm.
• Culinary & Wine Tasting: Indulge in a Tuscan lunch and sample regional wines.
• Comfort & Convenience: Travel in a private, air-conditioned Mercedes van with pickup from Florence.
• Scenic Routes: Admire breathtaking countryside views along the way.
• Timing & Schedule: Expect a full, well-paced day with approximately 9 hours of exploration.

What Makes This Tour Special

This private Tuscany day trip strikes a nice balance between guided structure and authentic exploration. From the moment you’re picked up in Florence, you’re whisked away in a comfortable, air-conditioned Mercedes vehicle—whether a sleek A/C minivan or similar—guided by an English-speaking driver with a deep knowledge of the region. This means you’re not just sightseeing; you’re gaining insights into Tuscany’s history, culture, and hidden gems every step of the way.

The tour’s flexibility allows for a custom experience, with the itinerary subject to change based on logistics or group preferences. This can be a real advantage, especially if your driver-guide is skilled at tailoring the day to highlight the towns and sights that resonate most with your interests.

Visiting Siena: The Horse Race and Medieval Atmosphere

Siena is the first highlight—famous for its Palio di Siena, a vibrant horse race held twice annually in the main square, Piazza del Campo. While the tour doesn’t seem to include a live race, you’ll get a sense of the town’s lively spirit through its architecture, narrow streets, and history.

One of the standout features here is the local guide in Siena, Adele, who reportedly shares an engaging, personal side of the city, walking you through neighborhoods and revealing stories that go beyond the usual tourist fare. Reviewers mention that she’s very knowledgeable, making the visit more meaningful.

You might find Siena’s Gothic cathedral impressive, and the town’s atmosphere is a mix of history and everyday life, creating a perfect backdrop for photos and soaking up the medieval vibe.

San Gimignano: The Tower-filled Town and Scenic Views

San Gimignano is often called the “Medieval Manhattan” for its skyline dotted with medieval towers—built for wealthy families to showcase status. This town exudes charm, with cobblestone streets, artisan shops, and stunning vistas of the Tuscan countryside.

We loved the way the tour allows for a relaxed stroll, giving ample time to visit the Torre Grossa—the tallest tower that offers panoramic views—and admire the town’s Gothic and Romanesque architecture. Don’t miss the chance to sample the famous gelato in Cistern Square, a treat highlighted by reviewers who say it’s the best way to cool down after exploring.

The visit to San Gimignano also includes a walk through the town’s cathedral and some time for photos of the picturesque streets and surrounding hills, which truly look like they belong on a postcard.

Wine Tasting and Tuscan Lunch: Savoring Local Flavors

An essential part of this tour is the visit to a carefully selected winery, where you’ll sample regional wines amidst scenic vineyard settings. Reviewers describe the wine tasting as generous, sometimes offering nearly a full glass per person—more than typical tastings in the U.S., which some found to be a delightful surprise.

The included Tuscan lunch is a traditional affair, featuring local dishes and a chance to relax and soak up the countryside atmosphere. Some reviews mention that the lunch is a shared cheese, salami, and prosciutto platter, which is a nice way to taste the region’s flavors without a formal sit-down meal.

Interestingly, a few visitors noted that the winery lunch might serve as a replacement for a restaurant meal, so if you’re expecting a full, sit-down lunch, you might want to confirm this with the provider.

Transportation & Timing: Comfort and Pacing

Travel is in a private Mercedes minivan or similar, which means less crowding and more comfort compared to larger group tours. The total duration is about 9 hours, starting at around 8 am and returning to Florence by 5 pm. The schedule includes plenty of scenic stops, photo opportunities, and enough time in each town to get a feel for the place.

Reviewers highlight the importance of this comfort—especially when compared to bus tours—allowing for a more relaxed experience. One review mentions that the timing was tight at certain points, but overall, the pacing was well-managed.

The tour’s flexibility is a plus—guides might change the order of stops depending on traffic or other logistical considerations, which helps keep the day smooth.

Small Group & Personal Attention

While the tour is described as private, it’s often booked as a small group, ensuring personalized attention. Guests frequently mention their guides’ friendliness, knowledge, and willingness to customize the experience—adding personal anecdotes, taking extra photos, or providing additional insights into local life.

Review highlights include stories from guides like Giuliano and Lorenzo, who were described as friendly, informative, and engaging, making the day more memorable.

Is This Tour Worth the Price?

At $662.98 per person, this experience is on the higher end, but the value comes from the private, tailored approach, expert guides, and the convenience of door-to-door service. For travelers wanting a curated day without the stress of driving or planning, this tour offers a lot of bang for your buck.

The inclusion of a wine tasting and Tuscan lunch adds to the value, especially when you consider the cost of similar experiences in Italy—where private guides, tastings, and meals can quickly add up. The reviews suggest that most find the quality of the guide, the scenery, and the overall experience to justify the price.

The Sum Up

This private tour from Florence to Siena and San Gimignano offers a well-rounded, authentic taste of Tuscany’s historic towns and countryside. It’s perfect for those who appreciate personalized service, expert insights, and a relaxed pace that allows you to truly take in the views and flavors of the region.

While the schedule might be a bit packed for those seeking a more leisurely exploration, the quality of guides, stunning scenery, and delicious wine tasting make it a memorable way to spend a day outside Florence.

If you’re after a hassle-free, insightful, and scenic experience that covers Tuscany’s highlights with a touch of luxury, this tour could be your ideal choice.

FAQs

How long is the tour?
The tour lasts approximately 9 hours, starting around 8 am and returning to Florence by 5 pm.

Is transportation comfortable?
Yes, you’ll travel in a private, air-conditioned Mercedes vehicle, which offers more comfort and space compared to larger group buses.

Can I customize the itinerary?
The itinerary is flexible in that the order of stops may change, depending on logistics, and guides often tailor the experience based on your interests.

Does the tour include a guided walk in Siena and San Gimignano?
Yes, you’ll have local guides in each town, like Adele in Siena, who share detailed insights and personal stories to enrich your visit.

What’s included in the wine tasting and lunch?
You’ll enjoy a visit to a carefully selected winery with wine tasting, which reviewers describe as generous. The traditional Tuscan lunch is a shared platter of local specialties, often including cheese, meats, and prosciutto.

Are children allowed?
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 enthusiasts?
Definitely. The scenic routes, panoramic views from San Gimignano, and picturesque towns provide ample photo opportunities.

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

Is there a minimum number of participants?
Yes, the experience requires a minimum number of travelers; if not met, the tour might be canceled or rescheduled with a full refund offered.

What if I need to cancel?
You can cancel free of charge up to 24 hours before the tour start time for a full refund.

This private Tuscan hill towns tour combines comfort, authenticity, and expert guidance, making it an excellent choice for travelers seeking a memorable, stress-free day among some of Italy’s most beautiful landscapes and towns.