Florence: Montalcino, Montepulciano & Val d Orcia with lunch

Discover the Stunning Charm of Tuscany with a Day Trip to Montalcino, Montepulciano & Val d’Orcia

If you’re looking for a way to experience authentic Tuscany beyond Florence’s well-trodden streets, this small-group day tour offers a perfect escape. Designed for lovers of history, wine, and breathtaking landscapes, it promises a mix of medieval charm, world-renowned wine tastings, and the kind of scenery that makes you want to snap photos every five minutes.

Two things we particularly appreciate about this experience are the expertly guided visits to historic villages like Montalcino and Montepulciano, and the chance to taste top-tier Brunello di Montalcino in a setting that feels both intimate and genuine. The tour also scores points for its small group size—limiting participants to just six—which makes for a more relaxed, personalized experience.

One consideration worth noting is the tour’s duration—about 10 hours. While it’s packed with sightseeing and tasting, it can feel a bit rushed for those who like to linger longer in each town. Still, if you’re eager to see as much of Tuscany’s countryside and historic spots as possible in a day, this is a solid way to do it. It’s ideal for travelers who enjoy wine, history, and scenic drives, and who value small-group intimacy for a more nuanced experience.

Key Points

• Authentic Visits: Small-group tours allow for a more personal experience, with attentive guides who are knowledgeable and flexible.
• Stunning Landscapes: Expect to travel through some of Tuscany’s most iconic scenery, from rolling vineyards to UNESCO-listed valleys.
• Medieval Villages: Montalcino and Montepulciano are wonderfully preserved towns, full of narrow streets and Renaissance architecture.
• World-class Wine: The highlight is the Brunello tasting, but you’ll also sample local specialties like olive oil and Pecorino cheese.
• Flexible Free Time: Ample opportunities to explore each town at your own pace, shop, or simply soak in the views.
• Value: The tour packs in transportation, expert guidance, tastings, and a delicious lunch—all in one day.

You can check availability for your dates here:

An In-Depth Look at Your Tuscany Day Trip

This 10-hour adventure from Florence is tailored for those eager to see the heart of Tuscany’s countryside without the hassle of driving or planning logistics. The journey begins early, with a meeting point conveniently located in front of the Starhotels Michelangelo. Once aboard, you’ll settle into a comfortable, premium vehicle that whisks you through Tuscany’s scenic roads—immediately setting the tone for a smooth, enjoyable day.

The Charm of Medieval Montalcino

Your first stop is Montalcino, a fortified medieval village famous worldwide for its Brunello di Montalcino wine. Expect to walk along narrow streets lined with artisan shops, wineries, and historic buildings, all encased within impressive boundary walls topped with towers. The town’s 14th-century fortress offers some of the best panoramic views of the Val d’Orcia, a UNESCO World Heritage Site. As one reviewer noted, this fortress provides “one of the most beautiful views onto Val d’Orcia,” and it’s easy to see why.

In the heart of Montalcino, you’ll visit a historic farm where you’ll taste Brunello and Rosso di Montalcino wines guided by a sommelier. These wines are the pride of the region, with Brunello often considered Italy’s finest red, renowned for its deep flavor and aging potential. The tasting includes local products such as extra-virgin olive oil and Pecorino cheese, offering a true taste of Tuscan culinary tradition. As one guest commented, “Lunch at the winery was excellent as well as the wines we enjoyed,” highlighting the quality of the experience.

Exploring the Enchanting Val d’Orcia

Leaving Montalcino, your journey continues through the Val d’Orcia, a landscape that looks like it belongs on a postcard. Expect rolling hills, dotted with iconic cypress trees, castles, and ancient villages. This area’s scenery is so picturesque that it’s been designated a UNESCO World Heritage Site, and for good reason. The landscape contrasts with the Chianti vineyards, offering lush greenery and a sense of expansive tranquility.

The Historic Town of Montepulciano

Next, you’ll arrive in Montepulciano, perched on a hill 600 meters above sea level. Renowned for its noble wine (Vino Nobile di Montepulciano), the town’s Renaissance buildings and steep streets provide an atmospheric setting for exploring at your own pace. With free time, you can stroll along the Renaissance piazzas, visit historic wine cellars, or simply enjoy the views over the surrounding vineyards.

A popular option is to add a second winery visit, which many find worthwhile for a deeper dive into local wine production. One reviewer emphasized the value of guided visits and tastings, noting the “knowledgeable and very flexible” guide, which made the experience particularly memorable.

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The Meal and Tasting Experience

The included lunch is more than just fuel—it’s part of the experience. Served with a panoramic view, the meal features local products, and the guided tasting of wines and oils enhances the culinary immersion. The homemade dessert offers a sweet finish, rounding out the hearty, authentic meal.

Practical Details and Reflection

Transportation is in a premium vehicle, comfortable for the small group, which means plenty of space for the scenery and conversation. The small group size (limited to 6 participants) ensures personalized attention, more interaction with the guide, and a relaxed pace.

The tour’s 10-hour duration means you’ll cover a lot of ground, which some might find slightly rushed, but most reviews highlight the well-balanced itinerary. As one guest observed, the guide “does not rush through the activities,” respecting the need for sufficient time at each stop.

Pricing is reasonable considering the inclusions—transfers, guided wine tastings, lunch, and expert guidance—offering good value for those eager to experience Tuscany’s highlights without the hassle of planning every detail themselves.

Who This Tour Is Perfect For

If you love a good glass of wine, enjoy exploring historic towns, and want to see some of Tuscany’s most iconic landscapes, this tour checks all those boxes. It’s especially suited for travelers who appreciate small groups and personal attention, making it feel more like visiting friends than a generic bus tour.

It’s ideal for those who want to combine sightseeing with tasting, and don’t mind a full day that includes some travel and walking. Since it’s not suitable for children under 10, pregnant women, or people with mobility issues, it’s geared more towards active, curious adults ready for a full immersion into Tuscany’s culture and scenery.

The Sum Up

This Florence-based tour offers a well-rounded experience that blends the best of Tuscany’s medieval charm, scenic beauty, and world-class wine. With expert guiding, personalized small-group attention, and authentic local tastings, it’s a wonderful way to deepen your understanding of Tuscany beyond the typical sights. Expect to leave with a richer appreciation for the region’s history, landscape, and culinary traditions.

The combination of stunning views, delicious food, and knowledgeable guides makes this tour especially appealing for those who want a genuine, memorable day in Tuscany. Whether you’re a wine lover, a history buff, or simply a traveler seeking beautiful landscapes and authentic experiences, this trip promises to deliver.

FAQs

How long is the tour?
The tour lasts approximately 10 hours, starting in the morning and returning in the evening. Check the specific start times when booking.

What’s included in the price?
You get transportation in a premium vehicle, wine tastings at two wineries, a guided visit, lunch with panoramic views, water, and a photo service. Guide services are also included.

Can I add extra winery visits?
Yes, there is an option to include a second winery tasting in Montepulciano, which many find enhances their experience.

Is this tour suitable for families?
It’s generally suitable for adults and older teens. It’s not recommended for children under 10, pregnant women, or those with mobility issues.

What should I bring?
Comfortable shoes, sun hat, camera, sunscreen, and water are recommended. Dressing appropriately for walking and sunny weather will make your day more enjoyable.

Do I need to worry about transportation logistics?
No, all transport is arranged and comfortable, allowing you to relax and enjoy the scenery without the stress of driving.

Is the tour canceled if the weather is bad?
You can cancel up to 24 hours in advance for a full refund, which is helpful if you’re concerned about weather conditions.

How much free time will I have in each town?
You’ll have ample free time to explore at your own pace, whether you want to stroll through Montalcino’s streets or taste wines in Montepulciano’s cellars.

Whether you’re after scenic views, historical towns, or top-notch wine, this tour offers a well-balanced slice of Tuscany that you’ll remember for years to come.

You can check availability for your dates here: