A day in Tuscany & Medieval Towns

When it comes to exploring Tuscany beyond the usual tourist trails, this private tour offers a chance to experience the region through the eyes of a local. For those seeking more than just the crowded city sights, this eight to nine-hour journey promises visits to secluded medieval villages, scenic countryside, and thoughtfully curated stops that most visitors miss. The all-in-one package includes private transportation, a knowledgeable guide, and a flexible itinerary tailored to your interests.

What we really love about this experience is the way it balances comfort with authenticity. You get a private vehicle to whisk you from one charming spot to another, with commentary that adds context without feeling overly scripted. Plus, the tour includes a lunch reservation at a traditional restaurant, making it easy to sample regional cuisine without the hassle of planning.

On the flip side, a possible consideration is that the tour does not include lunch — so you’ll need to budget extra for that. Also, while it’s a fantastic way to see multiple sites in one day, some travelers may find the pace a little brisk if they want to linger longer at certain spots.

Ideal for those who value personalized experiences, this tour suits travelers who prefer a relaxed, intimate day with expert insights, stunning scenery, and a touch of Tuscany’s lesser-known charm. It’s perfect for couples, small groups, or friends eager to explore with flexibility and ease.

Key Points

• Private, Customized Experience: You’re the only group, with a guide tailoring the day to your interests.
• Comfortable Transportation: An air-conditioned, private vehicle ensures a smooth ride across the countryside.
• Authentic Local Spots: Explore hidden medieval villages and scenic spots most travelers don’t visit.
• Expert Guides: Guides like Gianmarie and Francesco are praised for their knowledge and engaging personalities.
• Flexible Food Options: Lunch is at a recommended restaurant but is not included, giving you flexibility.
• Ideal for Small Groups: Cost is around $1,021 for up to 8 people, making it great value for a private experience.

Exploring Tuscany’s Off-the-Beaten-Path Charm

This tour is designed for travelers who want to go beyond the typical Florence day trip. Instead of crowded museums or popular landmarks, you’ll spend your day discovering medieval towns and hidden gems loved by locals. The journey starts with pickup from your accommodation in Florence, eliminating the hassle of navigating buses or rental cars. From there, your driver-guide takes over, sharing stories and insights as you traverse the Tuscan countryside.

The route is flexible but typically includes visits to towns like Lucca, San Donato, and other lesser-known spots. Reviewers mention that guides like Gianmarie and Francesco make the experience memorable with their friendly, knowledgeable approach. One reviewer noted that Gianmarie “planned a day in Tuscany that was unforgettable,” emphasizing how personalized and well-organized the experience can be.

The Value of Private Transportation

Having your own private vehicle means you can enjoy the scenery at your own pace. The air-conditioned van ensures comfort, especially on warm days, while the onboard commentary enriches your understanding of the landscape, history, and local culture. Travellers have appreciated the spaciousness, with some noting that groups of up to 7 or 8 fit comfortably in the vehicle.

Authentic Stops and Hidden Gems

One of the highlights, based on reviews, is the discovery of small towns and countryside that most travelers overlook. For instance, travelers mention visiting medieval villages like Monteriggioni and Pienza, with guides providing historical insights that bring these places to life. The chance to see where locals spend their weekends and to enjoy quiet streets far from tourist crowds adds genuine value.

Food and Wine Experience

While the tour does not include lunch, it arranges a reservation at a traditional restaurant, often at a family-run winery or a cozy trattoria. Reviewers rave about these meals, describing them as “delicious” and “authentic,” often with regional wines to match. Some have even enjoyed a wine tasting at a family winery, further deepening their Tuscan experience.

The Itinerary Breakdown in Detail

Stop 1: Start in Tuscany’s Hidden Corners

The tour kicks off once you’re picked up from your accommodation in Florence. The entire day is dedicated to exploring off-the-beaten-path sites. While the itinerary can be customized, most trips include visits to medieval towns such as Lucca and San Donato, places that are loved by locals but rarely on the typical tourist radar.

Visiting Medieval Villages

Traveling through narrow cobblestone streets, you’ll get a sense of Tuscany’s historical landscape. Reviewers like the one who called out Gianmarie for “making the day unforgettable” enjoyed wandering through these towns, admiring their well-preserved architecture and narrow alleys. Guides often share stories about the towns’ histories, adding a layer of storytelling that makes each stop more engaging.

Scenic Countryside & Hidden Spots

Expect plenty of scenic views, rolling hills, and vineyards. One reviewer described the experience as a perfect blend of “beautiful towns and wine tasting,” with the driver providing commentary about regional agriculture and local specialties. These vistas are ideal for photography, so don’t forget your camera.

Lunch at a Traditional Restaurant

The tour doesn’t include lunch, but it does secure a reservation at a family-run restaurant known for regional dishes. Guests often mention how the meal is a highlight—fresh, flavorful, and served in a cozy setting. Wine lovers will appreciate the suggestions for local wines to pair with their meal, elevating the whole dining experience.

Optional Wine Tasting

Some versions of this tour include a stop at a winery for tastings, which reviewers say are well worth the additional expense. It’s an opportunity to sample regional wines directly from small producers, adding a layer of authenticity to your day.

End of the Day: Return to Florence

Typically, the tour wraps up in the late afternoon, with a comfortable ride back to your accommodation. Many guests comment that the relaxed pace allows for a genuine appreciation of Tuscany without feeling rushed.

What Sets This Tour Apart?

Guides like Gianmarie and Francesco are frequently praised for their blend of professionalism and friendliness. One reviewer even claimed Francesco “was the BEST driver in all of Italy,” highlighting how a good guide/driver can make all the difference. Their in-depth knowledge and engaging personalities make learning about Tuscany a joy rather than a lecture.

The flexibility of the tour allows guides to customize stops based on your preferences, whether that’s more wine tasting, exploring a particular town, or simply soaking in the views. The private nature means fewer crowds and more tailored attention—something many travelers cherish after months of crowded museums and busy streets.

Pricing and How to Get the Best Value

At $1,021.75 for up to 8 people, this tour offers excellent value for a private experience. When you consider the cost of a private driver, transportation, and exclusive access to hidden spots, it’s a worthwhile investment for those wanting a curated, intimate look at Tuscany. The reviews suggest that the guides’ local knowledge and ability to personalize the day significantly enhance the experience, making the cost well worth it.

Who Is This Tour Best For?

This experience is perfect for travelers who crave authentic, personalized adventures rather than cookie-cutter group tours. It suits small groups or couples looking for a relaxed day exploring Tuscany’s lesser-known towns and countryside. If you’re a wine enthusiast, history buff, or simply someone wanting to avoid tourist traps, this tour will resonate.

It also works well for those who prefer comfort and flexibility—with private transportation and the ability to customize stops. If you’re someone who wants to learn about Tuscany’s culture through guided commentary, this tour provides plenty of opportunity for engaging stories and local insights.

Final Thoughts

For anyone visiting Florence and eager to see a more genuine side of Tuscany, this private tour delivers a memorable day of discovery. You’ll enjoy comfortable travel, expert guides, and a chance to step into medieval streets and quiet countryside that most visitors miss. The combination of flexible stops, authentic food, and knowledgeable guides makes it a top choice for those who want a personalized, immersive experience.

While the price might seem steep at first glance, the private nature, curated stops, and insider knowledge make this tour a solid investment in your Italian journey. It’s especially suited for small groups seeking a flexible, intimate way to explore Tuscany’s hidden charms without the stress of planning every detail.

FAQ

Is the tour suitable for all ages?
Yes, most travelers can participate, and the relaxed pace makes it accessible for many age groups.

What is included in the price?
The cost covers private transportation, an air-conditioned vehicle, onboard commentary, and all fees and taxes. Lunch is not included but reservations are made for you.

Can I customize the itinerary?
Yes, the guide can tailor stops based on your interests, focusing on medieval towns, countryside, or wine tasting.

How long is the tour?
It lasts approximately 8 to 9 hours, offering a full day of exploration without rushing.

Is pickup from my accommodation included?
Yes, pickup is offered from your chosen location in Florence, which adds convenience.

Are the guides knowledgeable?
Reviews highlight guides like Gianmarie and Francesco for their friendliness and extensive local knowledge.

What if I want to include wine tasting?
Some versions of the tour include a winery stop, and many reviewers recommend it for an authentic experience.

What should I bring?
Comfortable shoes for walking in towns, a camera, sun protection, and some cash for tips or additional purchases.

Will I have enough time at each stop?
The itinerary is designed to balance sightseeing with relaxation, but some sites may be visited briefly to fit the day’s schedule.

How far in advance should I book?
Most travelers book about 42 days ahead, especially in peak seasons, to secure their preferred date.

To sum it up, this private Tuscany tour offers a fantastic blend of comfort, authenticity, and expert guidance. It’s perfect for those who want to see the region through local eyes, exploring medieval villages, scenic countryside, and enjoying regional wines, all without the crowds or rigid schedules. If you value personalized service and unique experiences, this tour could be one of the highlights of your Italian trip.