A Practical Look at the Florence to Rome Private Transfer with Stops in San Gimignano and Siena

Planning a trip between Florence and Rome? If you’re considering a private transfer, this experience offers more than just a ride — it’s a chance to enjoy some of Tuscany’s most iconic villages along the way. Based on reviews and detailed descriptions, this tour seems to strike a good balance between comfort, flexibility, and scenery, making it a solid choice for travelers who want to cover ground without feeling rushed or stuck with rigid schedules.
What really catches the eye is the opportunity to visit two beautiful towns, San Gimignano and Siena, with live commentary from your driver. Plus, the convenience of door-to-door service by a deluxe Mercedes minivan keeps things comfortable and hassle-free. However, it’s worth noting that the price tag ($1,673.36 for up to 7 people) makes this a more premium option, suited best for those who value privacy and a flexible itinerary.
Our favorite features include the personalized stops—whether you want to explore medieval towers or enjoy a wine tasting at a winery—and the friendly, knowledgeable driver who acts as both guide and chauffeur. On the flip side, some travelers might find the cost steep if they’re just after a straightforward transfer without the stops or extras. This experience is best suited for travelers seeking comfort, local insights, and a more leisurely pace between two bustling cities.
Key Points

- Comfortable private transport eliminates the hassle of public transit.
- Flexible itinerary options allow choosing between sightseeing or wine tasting.
- Stops in San Gimignano and Siena offer a scenic and cultural glimpse of Tuscany.
- Live commentary from your driver adds personalized storytelling.
- Ideal for small groups (up to 7 people) seeking privacy and convenience.
- Cost reflects high-quality service and flexibility, making it a good value for those who prioritize comfort.
Prefer personalized experiences? Here are other private options we've covered in Florence
The Inside Scoop on the Transfer Experience

Traveling from Florence to Rome can sometimes feel like just a quick hop, but this private transfer elevates the journey into an experience. Instead of hopping on a crowded train or bus, you’ll be whisked away in an air-conditioned Mercedes minivan, which makes a huge difference in terms of comfort—especially if you’re traveling with a lot of luggage or just prefer a quieter ride.
The driver is an important part of this experience. With the ability to speak English and offer live commentary, your driver becomes a sort of casual guide, sharing stories about Tuscany’s traditions, history, and local life. This added layer of narration makes the ride more engaging and helps pass the time, especially on a route that takes around 2 hours.
Flexibility and Customization
One of the standout features is the flexible itinerary. You can opt for the classic visit to San Gimignano and Siena, or choose to incorporate a winery stop for lunch and wine tasting. This flexibility is a rare perk in private transfer services, especially since the driver is open to adjusting the schedule based on your preferences. After all, some might prefer to linger longer in Siena’s beautiful main square, Piazza del Campo, or explore San Gimignano’s towers and Duomo at their own pace.
In the reviews, Justin praises the driver’s ability to alter plans on the fly to ensure they made it to their destination on time while still enjoying a memorable stop. Similarly, Sherry highlights the driver’s friendliness and the spotless, comfortable vehicle that made the day enjoyable.
The Stops: San Gimignano and Siena
San Gimignano: Often called the “Manhattan of the Middle Ages,” this tiny village is famous for its skyline of medieval towers. Your driver will drop you off at the main gate, giving you around an hour free to walk, explore, and snap photos of its well-preserved architecture and the Duomo. It’s a perfect snapshot of medieval Italy, and the free time allows you to soak it all in without feeling rushed.
Siena: About 40 minutes from San Gimignano, Siena is renowned for its stunning Duomo and the Piazza del Campo, where the famous Palio horse race takes place twice a year. The city center is traffic-free, making it easy and enjoyable to walk. The driver can drop you close to the Duomo or wherever you prefer, giving you about an hour to explore. Many reviews emphasize Siena’s beautiful streets and vibrant history, making this stop a highlight.
Optional Winery Lunch and Tasting
If you opt for the winery stop, you’ll have a chance to enjoy lunch paired with wine tasting — though food and drinks are not included in the package. This could be a real treat if you’re a wine enthusiast or just want to experience a local vineyard in the tranquil Tuscan countryside. After lunch, your driver will continue to Rome, making this a full, relaxed day rather than just a transfer.
While in Florence, here are other experiences we've covered
- Private Transfer To or From Florence Airport ,Station and Hotel
- From Florence To Rome Direct Transfer In A Private Car
- Florence Airport Private Departure Transfer
- Florence Airport Private Transfer to the City
- Private Departure Transfer: Tuscany Hotels to Rome Fiumicino Airport or Rome Hotels
- Private Transfer from Florence and nearby to Sorrento or Positano
Pricing and Value

At $1,673.36 for a group of up to seven, the cost might seem high if you’re on a budget. But when you consider the private vehicle, the flexibility, and the stops, it starts to look more reasonable, especially if traveling with friends or family. For those who value comfort and personalized service, this is a good investment.
Compare this to public transport options, which can be less comfortable, more rushed, and less flexible. The fact that you’re paying for a door-to-door service and personalized attention means you’re paying for convenience — perfect for travelers who don’t want to worry about schedules, tickets, or navigating unfamiliar routes.
Who Is This Tour Best For?

This experience suits travelers who prefer comfort over cost and enjoy a more relaxed, personalized journey. It’s especially ideal if you want to maximize sightseeing time in San Gimignano and Siena without the hassle of public transit. If you’re traveling with a group, the price per person becomes more appealing, and the private nature means you can tailor the stops to your interests.
Plus, those who appreciate local insights shared by their driver will find this a plus. If you’re arriving in Florence and heading straight to Rome, or vice versa, and want to make the most of the scenery and culture along the way, this service fits well.
Final Thoughts

In any case, this private transfer from Florence to Rome, with stops at San Gimignano and Siena, offers a blend of luxury, flexibility, and cultural exposure. It’s not the cheapest option, but the personalized experience and scenic stops could make it worthwhile, especially for those wanting to avoid the crowds and enjoy a more intimate look at Tuscany.
If you value comfort, flexibility, and insider info, this service could be just the thing. It’s a good choice for travelers who prefer a tailored experience over a rigid schedule, or for those who want a scenic, hassle-free way to connect two of Italy’s most beloved cities.
One Way Private Transfer: Florence to Rome with Visit to San Gimignano and Siena
“Marco is extremely knowlegable and well connected to the area. I would recommend him for transfers and tours. We were rushed because we had plann…”
FAQ

Is this tour suitable for families?
While the tour isn’t specifically targeted at children, the comfortable private vehicle and flexible schedule could work well for families with older kids who enjoy sightseeing stops.
How long are the stops in San Gimignano and Siena?
You’ll have about 1 hour in each town for free walking tours, which is enough to see the main sights and get a feel for the place without feeling rushed.
Can I customize the stops?
Yes, the driver is flexible. You can choose to visit San Gimignano and Siena or opt for a winery lunch instead, depending on your preferences.
What is included in the price?
The price covers transport in an air-conditioned minivan and live commentary on board. Food, drinks, and entrance fees are not included.
How far in advance should I book?
Most travelers book around 90 days in advance, which suggests it’s a popular option worth reserving early.
What about cancellation?
You can cancel free of charge up to 24 hours before the experience, which is helpful if your plans change.
Is this a group tour or private?
It’s a private tour, so only your group participates, ensuring a more personalized experience.
What are the pickup locations?
The driver will pick you up at your centrally located Florence accommodation, making the start seamless.
Choosing this private transfer means opting for comfort, flexibility, and a touch of local charm — perfect for a memorable day traveling between Florence and Rome.
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- Florence: Private Photo Shoot
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- Florence: Gelato Making Class
- Private lessons in a Craft Lab with a Local
- Florence: Walking Tour & Wine Window – Small Group
- Florence: Accademia Gallery Timed Entry Ticket
- Florence Renaissance walking tour
- Wine Tour 6 hours 2 top wineries of Chianti Classico Limo Service
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