If you’re planning a trip to Florence and want to experience some of Tuscany’s most iconic towns without the hassle of driving yourself, a private tour to Siena and San Gimignano might just be the perfect choice. From what we’ve seen in reviews and tour descriptions, this experience offers a blend of scenic drives, rich history, and some of the best views the region has to offer — all tailored exclusively for your group.
What we really appreciate about this tour is how it combines a personalized service with the flexibility to customize your day, whether that’s stopping at a winery or enjoying a leisurely lunch with local wines. Plus, the fact that it’s a private experience means you can relax and explore at your own pace, away from the crowds.
On the flip side, one consideration is that lunch and wine tastings are paid for separately, so you’ll want to budget accordingly. Also, at around 8 hours, it’s a fairly full day, so it’s best suited for those who want an in-depth look at Tuscany’s treasures without feeling rushed. This tour is ideal for travelers who value comfort, flexibility, and a touch of exclusivity in their sightseeing.
If you enjoy scenic drives, historical towns, and the option to include some local wine experiences, this tour could be a fantastic fit. It’s especially good for those who prefer private, curated experiences over group tours packed with other travelers.
- Key Points
- The Itinerary: What to Expect on Your Day
- Starting Point and Schedule
- The Stop in Siena
- The Drive to San Gimignano
- Exploring San Gimignano
- Optional Extras and Flexibility
- Transportation and Comfort
- Duration and Timing
- Cost and Value for Money
- What’s included and what’s not?
- Insights from Reviewers: What Travelers Love
- Who Is This Tour Best For?
- The Sum Up
- Exclusive Private tour To Siena and San Gimignano
- Frequently Asked Questions (FAQs)
- More Private Tours in Florence
- More Tours in Florence
- More Tour Reviews in Florence
- More Florence experiences we've covered
Key Points

- Private, personalized experience tailored to your group
- Stunning views of Tuscany’s countryside and historic towns
- Flexible options for wine tastings or a relaxed lunch
- Well-reviewed for knowledgeable drivers and smooth logistics
- Cost, at around $925 for up to 6 people, offers good value considering exclusivity and comfort
- Timing and duration ensure thorough visits without feeling rushed
The Itinerary: What to Expect on Your Day

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Starting Point and Schedule
You’ll meet your driver at the Parcheggio Oltrarno in Florence at 9:00 am. From there, the journey kicks off with a scenic drive into the heart of Tuscany, where your driver—also your guide—will share interesting tidbits about the landscape and history of the region. The drive itself is part of the charm, with rolling hills, vineyards, and charming farmhouses passing by.
The Stop in Siena
Your first major stop is Siena, a city famous for its medieval architecture, winding streets, and the iconic Piazza del Campo. The tour allocates about 2 hours for exploration, which is usually enough time to stroll around the historic center, snap some photos, or grab a quick coffee. Since the admission tickets are included, you won’t have to worry about extra costs here.
One of the reviews highlights that the driver provides “all major and necessary information,” making the experience not just sightseeing but also educational. This is great if you’re the type to enjoy stories and context that bring the history alive.
The Drive to San Gimignano
After Siena, the tour continues on the scenic Chianti roads, renowned for their vineyards and lush landscapes. Depending on your preferences—if your driver has the time and your group is interested—you might stop at a local winery for tasting, or decide to have a leisurely lunch with wine at a restaurant or farm. These stops are not included in the tour price, so they’re optional and paid for locally.
Exploring San Gimignano
The highlight here is San Gimignano, known for its medieval towers and beautifully preserved architecture. This town offers a glimpse into Tuscany’s past, and the views from its hilltop are spectacular. It’s a place where you’ll want to take your time wandering the narrow streets, maybe picking up some local gelato, or just soaking in the atmosphere.
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Optional Extras and Flexibility
A major perk of this private tour is the ability to customize, if time allows. For example, the driver has mentioned they can arrange stops at local wineries or for lunch, so you can tailor the day to your interests. Many reviews praise the driver’s flexibility and knowledge, making the experience more personalized than a typical group tour.
Transportation and Comfort

The tour uses an air-conditioned vehicle, which is essential during hot Tuscan days. The cars are described as super comfortable and clean, contributing to a relaxed experience. Since only your group participates, you won’t have to contend with strangers or crowded buses—your ride is all about your comfort and privacy.
Duration and Timing
At around 8 hours and 15 minutes, this is a full-day experience, but the time is well-spent. It’s designed to balance sightseeing with leisure, giving you enough time to enjoy each town without feeling rushed. The tour starts at 9:00 am and ends back at your meeting point, providing a smooth, hassle-free day.
Cost and Value for Money

Priced at $925.73 per group for up to 6 people, this tour offers a good deal for a private experience. When you break down the cost, it’s roughly $154 per person if shared among six, which isn’t bad considering exclusive service, private transport, and the flexibility to customize your day.
Many reviews mention that the driver and guide are highly knowledgeable, and the vehicle’s comfort makes the day more enjoyable. The private nature of the tour means you can skip the large crowds and enjoy a more intimate, tailored experience.
What’s included and what’s not?
- Included: Air-conditioned vehicle, transportation, and Siena admission tickets.
- Not included: Lunch, drinks, and wine tastings, which are paid locally. This allows you to choose whether to indulge in a meal or tastings without being locked into a fixed schedule or cost.
Insights from Reviewers: What Travelers Love
Multiple reviewers highlight the stunning scenery and excellent wine options. One reviewer thanks their driver Pasquale for a “fantastic day,” emphasizing the comfort and professionalism. Another mentions that the driver, Franco, was “fun, informative, and made sure we tried small local wines,” which shows how personalized the experience can be.
The feedback also points out that this tour is well-suited for travelers who value comfort and flexibility. Several reviews mention that they appreciated the driver’s knowledge and the ability to customize stops, making for a richer, more relaxed day.
Who Is This Tour Best For?

This private experience is ideal for couples, friends, or small families looking for a hassle-free way to explore Tuscany’s most famous towns without the stress of driving or navigating public transport. If you’re someone who enjoys scenic drives, historical sites, and optional wine tastings, you’ll find this trip very rewarding.
It’s especially suitable if you’re seeking a personalized experience with a knowledgeable guide/driver, and if you prefer to avoid large tour groups. Keep in mind that the day is quite full, so it’s better for those who enjoy a well-paced but rundown of Siena and San Gimignano.
The Sum Up

All in all, this private tour to Siena and San Gimignano seems like a solid choice for anyone seeking a comfortable, customizable, and scenic day in Tuscany. The reviews suggest that the experience is not only well-organized but also enriched by the driver’s local knowledge and friendly approach. The price reflects the exclusivity and convenience, especially considering the high ratings and customer satisfaction.
If you’re after a relaxed, insider’s view of Tuscany’s historic towns, with some optional wine tastings thrown in, this tour delivers a lot of value. It’s particularly good for intimate groups who want to avoid the crowds and enjoy a tailored day with plenty of stunning views and cultural highlights.
For those who prioritize comfort, flexibility, and a personal touch, this private tour could be the highlight of your trip.
Exclusive Private tour To Siena and San Gimignano
“This was not our first trip with Tuscany Private Tours, but it is the first time I have written a review. We have visited many fascinating histori…”
Frequently Asked Questions (FAQs)

Is this tour suitable for children?
While the description doesn’t specify age restrictions, the full-day nature and focus on sightseeing and wine tastings suggest it’s best suited for older children or teenagers rather than very young kids. The private format means you could tailor the visit if traveling with teens interested in history and wines.
How many people can join the tour?
The tour is designed for groups of up to 6 people, making it an intimate experience with plenty of space and flexibility.
Are the stops at wineries included in the price?
No, wine tastings and meals are paid for separately on-site. The driver can help arrange stops if you wish, but costs are not included in the $925.73 fee.
What is the meeting point?
You’ll meet your driver at Parcheggio Oltrarno in Florence at 9:00 am. The experience ends back at the same place.
Is transportation provided?
Yes, an air-conditioned vehicle is included, ensuring comfort throughout the day.
Can I customize the itinerary?
Absolutely. The driver has mentioned the possibility of stopping at wineries or for a relaxed lunch, so you can tailor the day to your interests and schedule.
This private tour to Siena and San Gimignano offers a way to experience Tuscany’s highlights in comfort and style. Whether you’re a history buff, a wine lover, or simply looking for a scenic escape, it’s a trip worth considering.
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