Two days of Tuscany discovering the Nobile, Brunello, Chianti area

If you’re dreaming of Tuscany’s rolling hills, historic towns, and exquisite wines, this two-day tour promises to deliver just that. While we haven’t personally been on it, reviews suggest it’s a well-rounded experience that balances scenic beauty, cultural highlights, and tastings of some of Italy’s most renowned wines. It’s designed for those who want to see a lot without the hassle of planning every detail themselves.

One of the best things about this tour is how it combines visits to iconic towns like Montalcino, Montepulciano, Pienza, Siena, San Gimignano, and Castellina in Chianti — all packed into just two days. Plus, the inclusion of wine tastings at top estates means you get a real taste of Tuscany’s viniculture. We also love that the group is private, which adds a personal touch to the experience, and the guide seems to be knowledgeable and thoughtful.

A potential consideration is the pace — with so much to see and do, you’ll need to be prepared for some busy days. Also, meals are not included, so you might want to plan ahead if you’re hungry after the tastings or sightseeing.

This tour feels best suited for travelers who want a comprehensive, stress-free way to explore the Tuscan countryside, indulge in regional wines, and enjoy a mix of culture and scenic beauty. If that sounds like you, read on for a detailed breakdown of what to expect.

Key Points

• All-inclusive experience: Private transportation, wine tastings, and a comfortable overnight stay in an agriturismo.
• Rich cultural stops: Iconic towns like Siena, San Gimignano, and Montalcino are included, each offering unique sights.
• Wine lover’s dream: Tasting sessions at renowned wineries like Contucci Cantine, Piombaia, and Casa Emma.
• Flexible exploration: Some stops allow you to explore at your own pace, making it more personalized.
• Beautiful scenery: Expect stunning views of the Val D’Orcia and classic Tuscan landscapes.
• Ideal for those seeking convenience: No need to worry about transportation or bookings — it’s all handled.

An In-Depth Look at the Tuscany Tour

Setting the Stage: What Makes This Tour Stand Out?

This two-day Tuscany tour is carefully crafted to give travelers a taste of both historic Italy and world-class wines. For around $1,070, you get a comprehensive itinerary that covers many of Tuscany’s most celebrated towns and wine regions. While the price might seem steep, it’s important to see it as a package that saves you from planning logistics, booking multiple tours, and navigating unfamiliar roads.

It’s a private group experience, meaning your party gets exclusive attention from your guide, which often translates to a more personalized and flexible day. Plus, the inclusion of air-conditioned transportation and WiFi on board adds to the comfort, especially after long days of sightseeing.

Day 1: From Montepulciano to Montalcino

The day kicks off early at Piazza Adua in Florence, where you’ll meet your guide and begin your journey. The first stop is Piazza Grande in Montepulciano, a charming square famous for its medieval architecture and vibrant atmosphere. You’ll have about 1 hour and 30 minutes here to take in the views, walk around, and snap photos. Expect to see the Duomo and the Palazzo Contucci, which add historical depth to the visit.

Following this, there’s a stop at Contucci Cantine, a cellar where you’ll taste Nobile di Montepulciano, one of Italy’s prized red wines. The experience lasts about 30 minutes and is a great way to learn about local wine-making traditions.

Next, the tour takes you to Pienza, a tiny town renowned for its Renaissance architecture and stunning vistas of the Val D’Orcia. With 45 minutes to explore, you might stroll through its narrow streets or admire the panoramic views that have made it a UNESCO World Heritage site.

The afternoon continues with Montalcino, famed for its Brunello di Montalcino. You’ll visit the Fortezza and the Priori Palace, soaking in more history and local character. Afterward, a special visit to Piombaia wine cellar allows you to taste Brunello and learn about Sangiovese grapes — a highlight for wine enthusiasts. This tasting session lasts about an hour and is included in the tour.

Day 2: Siena, San Gimignano, and Chianti

The second day begins with a visit to Siena’s historic center, where the Duomo and Piazza Il Campo dominate the scene. With 1 hour and 30 minutes, you’ll have time to appreciate the medieval architecture, visit the famous tower “Torre del Mangia,” and see the fountain “Gaia.” Your guide will help you navigate and perhaps share some stories behind these landmarks.

Next, you’ll head to San Gimignano, often called the “Manhattan of the Middle Ages” for its skyline of medieval towers. Here, you get 1 hour and 30 minutes to wander, visit the Duomo, and—most famously—taste Vernaccia wine and the world-champion gelato at Gelateria Dondoli. This stop is perfect for a relaxed stroll and some delicious treats.

The afternoon includes a visit to Casa Emma, a renowned winery where you’ll taste Chianti and Supertuscan wines. You can also sample local olive oil and vinegar while learning about the Sangiovese grape, making this a sensory experience. The visit lasts about 1 hour and 15 minutes.

Finally, your tour concludes with a visit to Castellina in Chianti, a charming medieval town with the Via delle Volte and a fortress. This stop only lasts about 30 minutes but offers a lovely glimpse into Chianti’s history and landscape.

What’s Included and What’s Not

The tour fee covers all fees and taxes, making it easier to budget. It includes breakfast, two wine tastings, overnight accommodation in an agriturismo, and private transportation with WiFi. The driver is dedicated, so you won’t be sharing the ride with strangers, and the vehicle is air-conditioned for comfort.

Note that lunch is not included, so you should plan to bring snacks or plan for meals on your own. This allows flexibility for personal taste or dietary needs.

Our Honest Take: Is It Worth It?

From reviews, one standout element is the guide — Mario, who was praised for customization, kindness, and deep knowledge about the areas. This personal touch often makes a difference when exploring new regions, especially in a place as layered as Tuscany.

The wine tastings are a highlight—not just for the variety but for the quality and insights about the different wines and grapes. The stops at Pienza, Siena, and San Gimignano offer a good balance of cultural history and scenic beauty, while the visits to wineries give you a deeper appreciation for Tuscany’s winemaking traditions.

However, a busy schedule means you’ll be on the go pretty much all day. For some travelers, this pace might feel rushed, especially if you want to linger longer in each town. Also, since meals aren’t included, you’ll want to budget for lunch and dinner.

Who Will Love This Tour?

If you’re someone who enjoys wines and good company, this tour is a winner. It’s also great for those who want to see a lot of Tuscany without the stress of planning transportation or booking multiple tours. History buffs and architecture lovers will appreciate the stops in Siena and San Gimignano, while food and wine enthusiasts will find plenty to indulge in.

It’s particularly suited to travelers who value comfort and convenience—the private transfers, guided visits, and included tastings make it a hassle-free way to explore.

This two-day tour provides a thorough introduction to Tuscany’s top towns, scenic landscapes, and renowned wines. It’s well-suited for those who want a structured yet personalized experience, with a good mix of cultural sights and tasting opportunities. The inclusion of expert guides and private transport adds a layer of ease that many travelers will appreciate.

While the pace might be intense for some, the chance to sample Brunello, Nobile, Chianti, and Vernaccia wines—paired with visits to iconic hill towns—makes it a compelling choice. It’s especially ideal for those who enjoy wine, history, and stunning vistas all in one trip.

If you’re after a stress-free, immersive experience in Tuscany, this tour could be just what you need to make your dream trip a reality.

Is this tour suitable for families or children?
This tour is primarily designed for adults interested in wine, history, and sightseeing. While not explicitly family-focused, older children or teens with an interest in wine and culture could enjoy it.

Are meals included?
No, lunch is not included, so you may want to plan to bring snacks or dine in towns on your own.

What is the price per person?
The tour costs around $1,070.58 per person, which includes private transport, wine tastings, and one overnight stay.

How long are the stops at each town?
Stops vary between 30 minutes and 1 hour 30 minutes, allowing for sightseeing, tasting, and walking around.

Is transportation comfortable?
Yes, the transportation is air-conditioned with WiFi on board, making long drives more pleasant.

Can I customize the experience?
It’s a private tour, so your guide can tailor the experience to your needs, as noted by previous travelers.

What is the tour starting point and time?
Meet at Piazza Adua in Florence at 8:30 am. The tour concludes back at the same meeting point.

How far in advance should I book?
On average, travelers book about 41 days ahead, so planning early is advisable to secure your preferred dates.

Is this tour suitable for solo travelers?
Yes, although it’s a private group, solo travelers are welcome and will still enjoy the personalized service.

What happens in case of bad weather?
The tour is dependent on good weather. If canceled due to weather, you’ll be offered a different date or full refund.

This tour offers a well-rounded taste of Tuscany’s best towns and wines without the stress. If you’re ready to indulge in scenery, culture, and vino, it’s a solid choice for your trip.