From Florence: Siena, Cortona, Montepulciano & Val D’Orcia

If you’re dreaming of rolling hills, medieval towns, and the kind of scenic landscapes that seem almost too perfect, a guided day-trip through Tuscany might be just what you need. This tour from Florence offers a well-rounded taste of Italy’s iconic countryside, with visits to some of its most film-famous towns and a good dose of local food, wine, and history. While it’s a long day—lasting roughly 9 to 11 hours—there’s enough variety and stunning scenery to make it feel like a complete escape.

What we really like about this experience is the combination of expert guidance, authentic tastings, and the opportunity to explore charming towns at your own pace. Plus, the transport is by private 8-seater mini-van, which feels cozy and personal, rather than crowded or impersonal. The fact that you’ll visit locations made famous by movies like Under the Tuscan Sun and Letters to Juliet adds a romantic, cinematic layer to your adventure.

One possible consideration is that the tour involves quite a bit of driving—sometimes up to 1.5 hours between stops—so it’s best suited for those comfortable with long day trips. Also, it’s not tailored for travelers with mobility issues, given the walking involved in towns with cobblestone streets, and it doesn’t include hotel pickup.

This tour is ideal for travelers who want a comprehensive yet relaxed introduction to Tuscany’s highlights in one day. Food lovers, wine enthusiasts, and fans of film locations will find plenty to love here, especially if you’re keen to see lesser-known spots like Cortona and enjoy authentic farm tastings.

Good To Know

• Small Group Experience: Limited to 8 participants, making it more intimate and flexible.
• Authentic Tastings: Enjoy wine, cured meats, and local products directly from a family-run farm and a 14th-century cellar.
• Film Location Magic: Visit towns made famous by movies like Under the Tuscan Sun and Letters to Juliet for a romantic, cinematic vibe.
• Stunning Landscapes: Drive through and photograph the iconic Val d’Orcia with its rolling hills and cypress-lined roads.
• Expert Guides: Guides like Antonello and Dom get rave reviews for their local knowledge and personal touches.
• Ideal for a Full Day: The approximately 9-11 hour schedule fits well for travelers wanting a rundown without multiple days out.

You can check if your dates are available here:

A Deep Dive into the Tuscany Tour Experience

Starting from Florence: Convenience and Comfort

The tour begins early, around 8:00 am, with a meet-up at Porta Romana or another designated central Florence location. The private 8-seater mini-van is perfect for small groups, giving a cozy feeling and ease of conversation. Traveling in a small group means less time waiting and more personalized attention from your guide, which can really enhance the experience.

The journey begins with a scenic drive through the Tuscan countryside, a landscape that has been celebrated in countless movies and photographs. Expect to see gentle hills, patchwork fields, and iconic cypress trees—perfect for snapping photos and soaking in the vibe.

First Stop: Cortona – Film Fame and Authentic Charm

The first town on the agenda is Cortona, a hilltop town that Diane Lane famously made popular in Under the Tuscan Sun. Here, you’ll have about an hour to wander its narrow streets, explore artisan shops, and take in the views over the Valdichiana valley.

Reviewers highlight how guides like Dom are great at pointing out the film locations and interesting landmarks. One guest mentioned that they enjoyed getting basic information and pointers about what to see at each site, with enough free time to explore on their own. The town’s blend of history, art, and vibe makes it a perfect start, especially for those who love film settings or want authentic Tuscany charm.

Farm Visit & Tasting: Nature and Nibbles

Next, about 40 minutes from Cortona, you’ll visit a local farm with a reputation for high-quality products. Here, you can meet semi-wild Cinta Senese pigs foraging naturally, walk among olive groves and vineyards, and enjoy a curated tasting board. The tasting includes cured meats, bruschetta made from garden-fresh ingredients, and local wine, all served in a rustic setting.

Reviewers like Susan praised this part of the tour, mentioning how the farm tour and tasting left lasting memories. It’s a genuine experience that connects you with Tuscan food traditions. The farm’s location and focus on natural feeding add a layer of authenticity; you’re not just tasting wines, but also understanding the farm-to-table process.

More Great Thing To Do Nearby

Montepulciano: The Twilight Saga and Award-Winning Wines

The next major stop is Montepulciano, a walled town that fans might recognize from the Twilight movies. Here, you’ll have around 1.5 hours to wander through the historic streets, admire Renaissance architecture, and visit local shops.

A highlight is the wine tasting in a 14th-century underground cellar, offered as a complimentary bonus. The guide explains the significance of the Montepulciano DOCG wine, giving insight into its unique qualities. Several reviewers emphasize the quality of the tastings, with one describing the family-run winery as a warm, inviting spot where they learned about local wine production and enjoyed a lovely lunch with great conversation.

Breathtaking Views: Val d’Orcia

Driving through the Val d’Orcia, you’ll notice why this landscape has become so iconic—gently rolling hills, golden fields, and iconic cypress-lined roads. There’s a dedicated photo stop of around 15 minutes, giving everyone a chance to capture the scenery and breathe in the tranquility.

Reviewers consistently mention how the scenery here elevates the experience, with Brandy saying it’s a trip “filled with so much beauty.” The Val d’Orcia’s landscape isn’t just a backdrop; it’s a living, breathing part of Tuscany’s identity.

Siena: Medieval Magic

The last major stop is Siena, a city that’s also featured in Letters to Juliet. You’ll have about 1.5 hours to explore its medieval streets, bustling squares, and local artisan shops. The guide helps you navigate the highlights, but there’s plenty of time for independent wandering.

Susan appreciated the local insights during her visit, noting that guides like Elise and Francesca are excellent at pointing out the best spots. Siena’s charming atmosphere, with its narrow streets and historic piazzas, provides a perfect ending to the day.

Return Journey & Final Reflections

After Siena, the group begins the return trip to Florence, with an approximate 1.5-hour drive. The tour wraps up around 8:00 pm, giving you ample time to reflect on your day of discovery.

Practical Aspects and Value

Transportation: Traveling by private mini-van keeps the experience intimate and relaxed, avoiding the crowds often associated with larger tour buses. It also allows for quick getaways and flexible stops.

Duration & Pacing: At about 9 to 11 hours, the tour offers a full day of sightseeing without feeling rushed. The itinerary balances structured visits with free time, especially in towns like Montepulciano and Siena, giving you room to explore or relax.

Price & Value: At $186.92 per person, this tour offers a lot of value—covering transportation, guiding, tastings, and entrance fees in some sites. The inclusion of food and wine tastings, especially in a family farm and a historic cellar, enhances the experience beyond mere sightseeing.

Guides & Small Group: The positive reviews consistently praise guides like Antonello and Dom for their local knowledge, friendliness, and personalized approach. Limited to 8 people, the group size fosters a more engaging experience and better interaction.

Limitations: The tour isn’t suitable for those with mobility issues or pregnant women, given the walking involved and the physical nature of some visits. Also, note that hotel pickup isn’t included, so you’ll need to meet at designated locations.

Who Should Consider This Tour?

This experience is perfect for travelers looking to maximize their day in Tuscany without the hassle of planning logistics. Food and wine lovers will appreciate the tastings and farm visits, while film buffs will enjoy the locations made famous in movies. It’s also suited for those who prefer small groups and personal interaction over large, crowded tours.

However, if you prefer a more leisurely pace or have mobility challenges, you might want to consider other options. This tour is mainly for those comfortable with a packed schedule and plenty of walking on uneven streets.

FAQs

Is hotel pickup included?
No, the tour begins at a central Florence meeting point, and there’s no hotel pickup offered.

How long is the total duration?
The tour lasts approximately 9 to 11 hours, starting early in the morning and returning around 8:00 pm.

What is included in the price?
Transportation in a mini-van, a guided tour, tastings of local wines and products, and visits to key towns are included. Hotel/hostel pickup isn’t.

Are meals provided?
You’ll enjoy a tasting board at the farm and a wine tasting in Montepulciano, but meals are not included. Expect to purchase additional food if desired.

Is this tour suitable for children or older travelers?
It’s better suited for travelers comfortable with walking and long days. It’s not recommended for those with mobility impairments or pregnant women.

How many people are in the group?
Groups are limited to 8 participants, ensuring a more personalized experience.

Can I cancel?
Yes, free cancellation is possible up to 24 hours in advance, providing flexibility if your plans change.

Final Thoughts

This full-day Tuscan tour from Florence offers a well-rounded glimpse into the region’s most anticipated towns, combined with authentic food and wine experiences. The small group setup, knowledgeable guides, and scenic landscapes make it a memorable option for those wanting an immersive yet manageable day trip.

Perfect for first-time visitors eager to see iconic film locations and taste local flavors, this tour balances sightseeing with cultural richness. While it’s a long day with some driving, the variety of stops and quality of tastings ensure you’ll leave feeling you’ve truly experienced the heart of Tuscany.

If you’re seeking an authentic, guided adventure that covers scenic beauty, charming towns, and delicious bites—all with a small group feel—this tour is a worthwhile choice. It’s especially suited for those who want to avoid the hassle of self-planning but still enjoy a personalized experience.

You can check if your dates are available here: