PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

Exploring Tuscany in Style: A Deep Dive into the Private Full-Day Tour from Florence

This private tour promises a relaxed, personalized way to soak in some of Tuscany’s most iconic sights — Siena, San Gimignano, Monteriggioni, and a possible wine and food experience at a Chianti farm. It’s tailored for those who want to avoid the hassle of driving, prefer a guided experience, and enjoy a mix of cultural exploration and authentic local flavors.

What stands out most is how this tour combines comfort, flexibility, and local insight, all wrapped in a seamless package. The inclusion of door-to-door transportation in a luxury Mercedes van means you can sit back, take in scenic views, and focus on the experience rather than logistics. However, a key consideration is that this is a private tour with no official guide in the cities, which means the guiding relies heavily on your driver’s local knowledge and storytelling.

This experience suits travelers who love culture, are keen on tasting regional wines, and appreciate a carefully curated itinerary. If you’re looking for a full day of discovery with an emphasis on authentic Tuscany, this could be your ideal choice. Just be prepared for a busy schedule, and consider if a winery lunch (an optional addition) fits your pace and interests.

Key Points

• Private, personalized experience with door-to-door transportation in a luxury Mercedes van.
• Flexible itinerary, including free time at each stop for exploration or shopping.
• Expert driver with in-depth local knowledge — no official guide is included, so tips come from the driver.
• Ideal for wine lovers with an optional farm-to-table lunch and tastings.
• Efficient use of time with thoughtfully spaced stops, allowing plenty of sightseeing and picnicking.
• Highly rated — a perfect 5-star rating based on over 200 reviews, with many calling it a “must-do” in Tuscany.

A Closer Look at the Itinerary

Siena: The Jewel of Medieval Tuscany

Our journey kicks off in Siena, the undisputed star of Tuscany’s medieval scene. The city’s UNESCO-listed historic center is packed with architectural gems, winding streets, and a lively atmosphere. The main highlight here is the Piazza del Campo, famous for its distinctive shell shape and hosting the biannual Palio di Siena horse race. It’s not just a pretty square; it’s a hub of local life, where you can watch street performers, sip coffee, or browse artisan stalls.

Another stop is the Siena Cathedral (Duomo di Siena), a masterpiece of Italian Gothic architecture. Built in striking Italian Gothic style, this cathedral’s façade and interior are stunning, with intricate mosaics, frescoes, and a breathtaking marble floor. Reviewers have raved about the freedom to explore at your own pace, with one noting that “plenty of time was given at each stop,” which really helps in soaking up the atmosphere without feeling rushed.

Monteriggioni: A Medieval Fortress

Next, the tour visits the tiny, well-preserved fortress of Monteriggioni. Surrounded by original medieval walls, it’s a perfect spot for a quick walk and some photos. The quiet charm of this village makes it a relaxing contrast after Siena’s bustling streets. Since there’s no entrance fee, this is a leisurely break where you can wander along the ramparts, imagine medieval life, or enjoy a meal at a local restaurant.

Reviewers have said it’s “a lovely spot for a short walk after lunch,” and many appreciated the chance to stretch their legs in a setting that’s very much like stepping back in time. It’s a quick, authentic experience rather than a tourist trap — ideal for those wanting a taste of history without a big time commitment.

The Optional Chianti Winery Lunch

One of the true highlights — or optional extra — is a visit to a biodynamic farm or winery in Chianti, where you can indulge in organic, freshly prepared dishes paired with local wines. Many reviews emphasize how exceptional this experience is. Guests loved the cuisine, describing it as “fantastic,” with local specialties like fresh pasta, cured meats, and seasonal vegetables, complemented by Super Tuscan, Chianti, and Vernaccia wines.

The setting offers panoramic views of vineyards and olive groves, making the meal a feast for both the senses and the eyes. Reviewers frequently mention how this lunch adds a special touch, turning a sightseeing day into a full-on indulgence in Tuscan flavors. It’s a chance to learn about organic and biodynamic farming while enjoying a relaxed meal away from the crowds.

San Gimignano: The Manhattan of the Middle Ages

The final stop is San Gimignano, famous for its skyline of medieval towers. Often called the Manhattan of Tuscany, this town looks like a fairytale, with towers rising dramatically from narrow streets. Visitors can explore at their own pace, with time to visit shops, admire the view from the town walls, or enjoy the world-renowned Dondoli ice cream shop, praised by many as the best in the world.

Reviewers love how San Gimignano feels like stepping into a time capsule from 1300 AD. The town’s unique architecture and lively piazza make it a perfect place for a relaxed walk and some souvenir shopping. Since it’s the last stop, it’s a great way to end the day on a high note.

Transport and Timing: Making the Most of Your Day

The tour’s transportation is a luxury Mercedes minivan, which is roomy enough for your private group of up to 8 people. This means everyone can stretch out and enjoy the countryside views comfortably. Travel times are carefully planned, with roughly 2 hours allocated to Siena, Monteriggioni, and San Gimignano, plus extra time for the optional winery lunch — usually about 2 hours for that.

Departure is suggested at 9:00 am, but flexible scheduling is available during reservation. The tour lasts about 8 to 9 hours, giving you a full day of sightseeing without feeling rushed. The driver is also your guide, sharing insights along the way, although there’s no official guide in the cities. This works well for those who enjoy a more conversational, informal insight rather than a structured tour.

Authentic Experiences & Authentic Drivers

Multiple reviews highlight how knowledgeable and friendly the drivers are. Many guests mention Alessandro, who’s often praised for his storytelling, enthusiasm, and flexibility. One reviewer shared, “Alessandro was fantastic with his knowledge of wine and the area,” which clearly adds value to the experience. You’ll also appreciate that the tour is exclusive to your group, so all your questions and interests are accommodated without having to compete with strangers.

Price & Value: Is This Worth It?

At $377.35 per person, the tour might seem like a splurge, but considering it covers transportation, a private driver, and the potential for a gourmet winery lunch, it offers great value. The reviews consistently praise the quality of service, the flexibility, and the depth of local insight—making it a worthwhile investment for those wanting a seamless, high-end Tuscany experience.

For travelers who prefer not to rent a car or navigate public transport, this all-in-one package saves time and effort. Plus, the opportunity to taste organic wines and local dishes elevates the experience beyond just sightseeing.

Who Will Love This Tour?

This experience is perfect for wine enthusiasts, history buffs, and food lovers who want a personalized, comfortable day exploring Tuscany’s highlights. It’s also ideal for travelers who prefer flexible schedules and enjoy a mix of guided insight and free time.

If you’re traveling with family, friends, or a small group, the private nature and tailored pace make it particularly appealing. However, if you’re seeking a guided city tour or strict group schedule, this might not be the best fit.

The Sum Up

This private full-day tour from Florence offers a smart, comfortable way to explore Tuscany’s most celebrated towns without the stress of driving or navigating public transport. The combination of beautiful scenery, engaging driver-guide, and optional gourmet lunch makes it a well-rounded experience for those who love authentic local flavors, medieval architecture, and picturesque views.

The flexibility and quality of the service mean you can truly customize the day, whether it’s focusing on sightseeing, shopping, or wine tasting. It’s a particularly good choice for travelers who want a comprehensive, hassle-free day and are happy to pay a bit more for the added comfort and personalized attention.

Overall, if you’re after a memorable, well-organized Tuscany experience with excellent reviews to back it up, this tour is a strong contender. Just remember to book early — over 100 guests tend to plan this trip about four months in advance, which shows how popular it is.

FAQ

Is the tour suitable for families with children?
Yes, it’s a private tour that can be tailored for families. Just note that minors under 18 aren’t allowed to drink wine, but the experience is still engaging and educational for children.

How long is the travel time between stops?
The itinerary allows for about 2 hours at each major site, with driving times spaced out comfortably so you can enjoy the scenery without long car rides.

Is lunch included in the price?
The winery lunch is an optional extra, costing between €55 and €65 per person. Many reviews say it’s well worth the extra, especially for wine lovers.

What if it rains?
Umbrellas are provided by your driver, so you can still enjoy the outdoor parts of the tour in light rain.

Can I customize the itinerary?
Yes, during reservation you can specify preferences or ask for arrangements like a winery lunch or additional stops, within the tour’s structure.

How many people are in a typical group?
This tour is exclusive to your private party, with a maximum of 8 guests, ensuring a personalized experience.

Is a guide included in the cities?
No, the driver serves as your guide, sharing insights during the drive and at each stop. Reviewers appreciate the knowledgeable and friendly driver, Alessandro.

Can I cancel if my plans change?
Yes, cancellations are free up to 24 hours before the tour, allowing flexibility if your plans shift.

This comprehensive, well-reviewed tour offers a wonderful mix of culture, scenery, and flavor — all in a day that feels both relaxed and packed with discovery. Whether you’re a first-timer or a seasoned Tuscany lover, it’s a hassle-free way to make the most of your time in Florence’s surroundings.