One Way Private Transfer: Florence to Rome with Visit to San Gimignano and Siena

Traveling between Florence and Rome doesn’t have to be a mundane train ride or a crowded bus. This private transfer service offers a more comfortable, customizable way to get from one city to the other—plus the chance to explore two enchanting Tuscan towns along the way. With a dedicated driver, you’ll enjoy personalized commentary, scenic views, and flexibility in your stops.

What we love most about this experience is how it combines efficient transport with authentic sightseeing—no rushing, no rigid schedules. The highlight for many travelers is the opportunity to visit San Gimignano, with its famous medieval towers, and Siena, renowned for its stunning Duomo and historic square. A possible downside? The price tag might seem steep, but when you factor in comfort, flexibility, and personalized attention, many say it’s worth every euro. This tour is ideal for those who value comfort, want to avoid public transport hassles, and love discovering Italy’s hidden gems at their own pace.

Key Points

• Flexible itinerary allows you to choose between sightseeing or a winery lunch stop.
• Private, air-conditioned Mercedes minivan ensures comfort and style.
• Authentic insights from your driver enrich your understanding of each stop.
• Ideal for groups up to 7, making it a cost-effective way to explore with family or friends.
• Stops in San Gimignano and Siena are carefully timed for a relaxed visit.
• Live commentary adds context and stories to each destination, making sightseeing richer.

An Overview of What to Expect

This is a private, one-way transfer experience designed for travelers who want more than just point-to-point transport. Starting in Florence, your friendly, English-speaking driver will greet you at your centrally located accommodation, ready to whisk you away in a luxury Mercedes minivan. The journey lasts approximately two hours, but it’s what happens along the way that makes it special.

Your driver isn’t just a chauffeur; they double as a local guide. Expect lively commentary about Tuscany’s landscapes, cultural quirks, and history. You’ll be traveling through rolling hills and vineyards, with plenty of photo opportunities.

San Gimignano

Your first stop is San Gimignano, often called the “Manhattan of the Middle Ages” due to its iconic towers. When you arrive, you’ll be dropped off right at the main gate, giving you a full hour to explore this compact, picturesque village. Its medieval structures are incredibly well-preserved, and the skyline with numerous towers is truly a sight to behold.

In the reviews, travelers mention how their driver, Marco, was extremely knowledgeable and well-connected, making the experience more enriching. One guest highlighted that Marco tailored the stop to include a stunning walk through medieval streets and pointed out notable sites like the Duomo, an excellent example of medieval art.

Siena

From San Gimignano, it’s about a 40-minute drive to Siena, a city famed for its beautiful Duomo and the Piazza del Campo, site of the legendary Palio horse race. The city center was closed to traffic in 1966, making it very walkable and easy to navigate. Your driver will drop you at a convenient spot—either near the Duomo or the square—so you can enjoy a one-hour free walking tour.

Reviewers appreciated the personalized approach. Sherry B noted that Marco was “knowledgeable, friendly, and an excellent driver” who allowed ample time for sightseeing. She also mentioned how the driver asked them to regroup in just 60-90 minutes, making their visit relaxed rather than rushed.

Customizable Stops: Wine Tasting or Sightseeing

One of the most appreciated aspects of this tour is its flexibility. On the day, you can opt to stick to the original plan—visiting San Gimignano and Siena—or you can switch things up to include a lunch at a winery with wine tasting. The driver can take you directly from San Gimignano to a vineyard, where you can enjoy local wines and regional delicacies.

While lunch and wine tasting are not included in the price, the option is available, which many guests find adds incredible value to their day. After lunch, your driver will continue the journey to Rome or Fiumicino Airport, ensuring your transfer is seamless and personalized.

Why Choose This Transfer?

Traveling between Florence and Rome, especially if you’re keen to see more than just the cities, can be tricky with public transport. Trains are quick but often inflexible, and buses can be crowded and uncomfortable. This private transfer not only offers comfort and convenience but also turns a simple journey into a mini sightseeing adventure.

The deluxe Mercedes minivan ensures a quiet, smooth ride with air conditioning, and the live commentary enriches your understanding of Tuscany’s history, architecture, and way of life. The one-hour stops allow for a relaxed exploration of San Gimignano and Siena, without feeling rushed—something many travelers mention as a highlight.

The flexibility of the itinerary is a game-changer. If you’re short on time but want to see the highlights, sticking with the original plan works well. But if you love wine or local cuisine, switching to the winery stop is a fantastic way to indulge in authentic flavors. The driver’s willingness to adapt makes this experience stand out compared to rigid group tours.

The Value for Money

At $1,601.83 for up to seven people, the per-person cost might seem high at first glance. However, considering the private nature of the tour, the comfort of a Mercedes vehicle, and the personalized attention, many travelers find it excellent value—especially for groups or families.

Compared to booking separate transport and guided tours independently, this package combines convenience, flexibility, and expert insights—a real plus for those who prefer stress-free travel. The reviews reinforce that the driver’s local knowledge and friendly demeanor significantly enhance the experience.

Real Traveler Insights

Justin_P pointed out how their driver, Marco, “was extremely knowledgeable and well connected to the area,” making the stop in Siena especially worthwhile. He appreciated the flexibility to adjust plans and how Marco changed plans to ensure they reached their destination on time—a key benefit of private tours.

Sherry B also emphasized Marco’s friendliness and professionalism, noting her family’s comfort in the immaculately clean minivan and how he tailored the timing for sightseeing, making their day relaxing and enjoyable.

These reviews highlight the importance of a knowledgable and flexible driver, turning what could be a simple transfer into an engaging, personalized experience.

Practical Details and Tips

• Meeting point is typically your centrally located Florence accommodation—easy to arrange with your driver.
• The tour departs at 9:00 am, giving you ample time for stops and exploration.
• Duration of the entire experience is around two hours of driving, plus the time spent in San Gimignano and Siena.
• Food and drinks are not included, so consider bringing snacks or planning to buy food during your stops.
• You can cancel free of charge up to 24 hours in advance—perfect if your plans change unexpectedly.
• This is a private tour, only your group will participate, ensuring a personalized experience.

Who Is This Tour Best For?

This experience is perfect for groups of friends, families, or couples who want a comfortable, private way to travel between Florence and Rome while exploring charming Tuscan towns. If you’re a traveler who appreciates local stories, scenic views, and a flexible schedule, this tour ticks all boxes.

It’s also ideal for those with limited time but who want a taste of Tuscany beyond the main cities. The option to include a wine tasting makes it perfect for foodies and wine lovers eager to enjoy regional flavors in a relaxed setting.

Lastly, if you prefer avoiding crowded public transport and value personalized, flexible arrangements, this private transfer will be right up your alley.

Frequently Asked Questions

Can I customize the stops during the transfer?
Yes, the driver is flexible. You can choose to visit San Gimignano and Siena or opt for a winery lunch instead. This can be arranged directly with your driver on the day.

What is included in the tour?
The package includes live onboard commentary, transport by air-conditioned minivan, and the stops in San Gimignano and Siena. Food and drinks are not included.

How long do I have in each town?
You get approximately one hour in San Gimignano for sightseeing and a similar amount of time for Siena. The driver will organize your timing to keep the schedule relaxed.

Is this experience suitable for large groups?
Yes, up to 7 people can be accommodated in the private Mercedes minivan, making it a good value for families or small groups.

What if I want to visit a winery?
You can choose to include a winery visit for lunch and wine tasting instead of sightseeing in Siena. The driver will help coordinate this on the day.

What if my plans change?
You can cancel for free up to 24 hours before the experience. The driver is flexible and can adjust the itinerary if needed.

Do I need to speak English to enjoy this tour?
Yes, the driver speaks English and will provide commentary to enhance your understanding of the places visited.

What is the pickup location?
Pickup is offered from your centrally located Florence accommodation, making it convenient and hassle-free.

Can I book this last minute?
Most travelers book about 90 days in advance, but availability depends on the date. Confirmations are sent within 48 hours of booking.

This private transfer from Florence to Rome with stops in San Gimignano and Siena offers a combination of comfort, flexibility, and authentic sightseeing. It’s a smart choice for those who want to avoid the stress of public transport and prefer a personalized experience. The ability to switch between sightseeing and a wine tasting makes this tour adaptable to your interests.

Travelers who appreciate engaging stories from knowledgeable guides, scenic landscapes, and the freedom to craft their day will find this experience well worth it. The small group size ensures intimacy and attentive service, making it ideal for families, friends, or couples seeking a relaxed yet enriching journey through Tuscany.

While the price may seem high, the combination of private transportation, expert commentary, and custom stops provides significant value—not just a transfer, but a memorable part of your Italian adventure.

To sum it up, if you’re after a smooth, flexible, and insightful way to travel between Florence and Rome while exploring Tuscany’s treasures, this private transfer ticks all the right boxes. It’s particularly suited for those who love comfort, local stories, and personalized experiences, making your Italian trip all the more special.