Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Florence

A Full-Day Slice of Tuscany: Siena, Monteriggioni, San Gimignano, and Pisa

This private tour from Florence promises a taste of Italy’s most beloved medieval towns, iconic landmarks, and scenic rolling hills. With a carefully curated itinerary, you’ll visit Pisa’s famous Leaning Tower, wander through the UNESCO-listed streets of San Gimignano and Siena, and enjoy a leisurely wine tasting in the Tuscan countryside. The tour is designed for those who want an in-depth, flexible experience — with the comfort of private transportation and the ability to customize your day.

What I really like about this experience is its blend of sightseeing and authentic local flavor. First, the scenic drive through Tuscany’s lush hills offers a calming break from city crowds. Second, the wine tasting at Tenuta Torciano is a highlight — a chance to sample excellent wines and try a delicious light lunch amidst the countryside. However, a potential consideration is its price point — at over $900 per person, this isn’t a budget option, but the quality and personalization could well justify the cost.

One possible drawback: since the driver cannot accompany you inside the major sites, you’ll need to plan your sightseeing time accordingly. Still, the driver’s tips and guidance are noted as very helpful, making navigation easier.

Key Points / Takeaways

Private, customizable experience offers flexibility to tailor your day
Visit two UNESCO World Heritage sites: Siena and San Gimignano, both packed with history and charm
Enjoy a scenic drive through Tuscany’s picturesque hills, perfect for landscape photography
Includes a wine tasting with light lunch at an exclusive farm winery, a real treat for wine lovers
Excellent guides and drivers make sure you get insider tips and a friendly vibe
Pisa’s Leaning Tower is a must-see icon, with plenty of nearby architectural gems to explore

Exploring Tuscany in Style: The Itinerary Breakdown

This tour is a well-balanced mix of must-see landmarks and authentic local experiences. Starting early from Florence, the pickup in a private, air-conditioned minivan sets a comfortable tone. As someone who appreciates smooth travel, I find that having a dedicated driver makes a big difference, especially when juggling multiple destinations.

First Stop: Pisa’s Piazza dei Miracoli
You’ll get a quick, efficient look at the famous Leaning Tower along with the cathedral, baptistery, and cemetery. The guide or driver can offer tips on the best angles for photos and where to go next, but keep in mind you’ll be on your own inside these sites. This stops is ideal for those who want a picture of the tower and some quick sightseeing without the hassle of navigating alone.

Next: San Gimignano
Known as the Town of Fine Towers, San Gimignano is a postcard-perfect medieval hilltop village. With about a dozen towers still standing, it’s fascinating to walk through the UNESCO World Heritage-listed streets. The views from the walls are especially noteworthy — you’ll love the way the landscape unfolds beneath you. Many travelers, including one reviewer who called it an “unforgettable skyline,” find San Gimignano’s medieval skyline truly breathtaking.

En route to Siena: The Tuscany Countryside and Monteriggioni
The drive through gently rolling hills is the kind of scenery that makes Tuscany famous. Before reaching Siena, the tour includes a visit to Monteriggioni, a walled medieval town that’s like stepping into a living history book. Its stone halo atop the hill creates a striking silhouette and offers a real sense of stepping back in time, as one reviewer described it as “one of the most memorable towns in Italy.”

Final stop: Siena
Declared a UNESCO site, Siena is a feast for the senses — its cathedral, the Piazza del Campo, and winding streets exude medieval charm. You’ll have about two hours to explore at your leisure, which is ample time to soak in the sights. Many reviews praise the guides, like Elena, for being knowledgeable yet personable, making the experience lively and engaging. The city’s famous Palio horse race, held twice a year, adds extra excitement to its vibrant, historic atmosphere.

Wine Tasting and Light Lunch at Tenuta Torciano
This exclusive farm winery offers stunning panoramic views and a chance to taste some of Tuscany’s finest wines. The included light lunch is a real bonus — a chance to relax, savor local flavors, and enjoy the countryside ambiance. Many travelers rave about the quality of the wines and the friendliness of the hosts, with one reviewer calling it “spectacular” and highlighting the “good value for money.”

Here are more great tours and experiences we've reviewed in Florence

Transportation and Timing: What to Expect

Travel is in a private, fully insured, air-conditioned minivan, which can accommodate up to eight people. This makes the journey both comfortable and intimate. The tour starts early at 8:00 am, giving you plenty of time to enjoy each stop without feeling rushed. Since the driver cannot go into the sites with you, plan to spend your time exploring independently once you arrive.

The total duration of about 9 hours means you’ll get a full day of sightseeing, but still have time to relax and reflect during the drive back to Florence. Many reviews mention how the driver or guide adds value, sharing tips and local insights that enhance the experience.

Who Will Love This Tour?

This experience is best suited for travelers who value a private, flexible itinerary and wish to see multiple highlights of Tuscany in one day. It’s ideal if you enjoy scenic drives, medieval towns, UNESCO sites, and wine tasting — and you’re comfortable with a somewhat luxurious price point.

Couples, small groups, or families looking for a personalized day trip will appreciate the attention to detail and the opportunity to customize. It’s especially good for those who want to avoid crowded tours and prefer a more intimate, authentic experience.

Price and Value Analysis

At $921.92 per person, this tour isn’t cheap. But considering the private transportation, guided insights, wine tasting, and the opportunity to visit five key locations, the value becomes clearer. The convenience of a dedicated driver, combined with high-quality experiences and the flexibility to tailor your day, could make this a worthwhile splurge — especially for those celebrating a special occasion or seeking a more personalized view of Tuscany.

Final Thoughts

This tour offers a carefully curated taste of Tuscany’s most iconic towns, combined with the comforts of private transport and expert guidance. You’ll walk away with stunning photos, a good knowledge of local history, and perhaps a few bottles of delicious regional wine.

While the price might be steep for some, the combination of flexibility, authentic experiences, and scenic beauty makes it a compelling choice for those wanting a comprehensive yet relaxed day in Tuscany.

If your goal is to experience Tuscany’s highlights without the hassle of planning or navigating public transport, this private tour could be your best option. It’s perfect for travelers who want a richer, more personalized look at Italy’s medieval heart.

Here's some more things to do in Florence

FAQ

How early does the tour start?
The tour begins at 8:00 am, giving you a full day of sightseeing without feeling rushed.

Is this a private tour?
Yes, this is a private experience, meaning only your group will participate, and it can be customized if you request it in advance.

What transportation is used?
You’ll ride in a fully insured, air-conditioned minivan driven by a professional English-speaking driver.

Are guides included at each stop?
A dedicated local licensed guide is available in Siena if you select that option, but the driver provides tips and guidance for other locations.

How much time do I have in each town?
You’ll spend about an hour in San Gimignano, two hours in Siena, and a brief stop in Pisa, with flexibility depending on your interests.

Is there a wine tasting?
Yes, a wine tasting and light lunch are included at an exclusive farm winery in the Tuscan countryside.

Can I customize the itinerary?
Yes, the tour can be tailored to your preferences, making it ideal for those who want a personalized experience.

What should I wear?
Comfortable shoes for walking and layers for variable weather are recommended, especially since you’ll be exploring medieval streets.

In sum, this full-day private tour offers a well-rounded, authentic taste of Tuscany’s best. It’s perfect for those who want comfort, flexibility, and meaningful encounters with Italy’s timeless towns and landscapes.