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

An Authentic Two-Day Journey Through Tuscany’s Finest Towns and Wineries

This two-day Tuscan tour offers an immersive experience in some of Italy’s most iconic towns, including Montalcino, Montepulciano, Pienza, Siena, San Gimignano, and the Chianti region. Priced at $1,070.58 per person, the trip is designed for those eager to explore Tuscany’s historic streets, stunning landscapes, and world-famous wines without the hassle of driving. The tour is ideal for small groups, ensuring a personalized experience led by knowledgeable guides, with private transportation and air-conditioned vehicles.

While the tour covers a lot of ground in just two days, the carefully curated stops and wine tastings make it a comprehensive introduction for anyone interested in Tuscan culture, history, and wine. Travelers should note that lunch is not included, so planning for meals during free time is advisable. This guided journey offers a balanced mix of sightseeing, tasting, and cultural appreciation, perfect for a quick yet fulfilling escape into Tuscany’s most celebrated regions.

Key Points

• Two days of exploring Tuscany’s most renowned towns and wine regions
• Includes guided visits to towns like Montalcino, Montepulciano, Pienza, Siena, and San Gimignano
• Wine tastings at two select wineries, with a focus on Nobile, Brunello, Chianti, and Vernaccia
• Private transportation ensures comfort and flexibility during the trip
• Tour departs from Florence at 8:30 am and includes a overnight stay in an agriturismo
• Suitable for most travelers, with confirmation received at booking and free cancellation options

Starting in Florence: The Meeting Point and First Impressions

The tour begins at Piazza Adua in Florence at 8:30 am, where the guide will greet the group before setting off. The transportation is private and air-conditioned, with WiFi onboard for added convenience. This start time allows travelers to make the most of the two days, and the small group setting ensures a personalized experience.

The comfortable vehicle makes scenic drives through Tuscany’s countryside, giving a preview of the rolling hills and vineyards that define the region. The tour is well-organized for most travelers, with near public transportation access at the meeting point.

Exploring Montalcino’s Historic Charm and Brunello Wineries

The first day features a visit to Montalcino, famous for its Brunello di Montalcino wine. The tour stops at the Fortezza and the Palace of the Priori, where the historic squares and medieval walls create a picturesque backdrop. The 45-minute visit offers a look at Montalcino’s ancient architecture and panoramic views.

A highlight is the stop at Piombaia wine cellar, where the group samples Brunello wine, Rosso di Montalcino, and Sant’Antimo. The tasting includes insights into wine production and Sangiovese grapes, making it an educational experience as well as a sensory delight. The 1-hour tasting is included in the tour price, offering a chance to appreciate local wines directly from the producers.

Discovering Montepulciano’s Artistic Streets and Nobile Wines

Next, the tour explores Montepulciano, with a 1 hour 30-minute stop at Piazza Grande, the town’s historic square. The Duomo, Palazzo Contucci, and other notable buildings frame the square, providing a sense of medieval grandeur. The Contucci Cantine visit allows for a tasting of Nobile di Montepulciano, a red wine with a free admission to the cellar.

This stop combines architecture, history, and wine culture, giving visitors a taste of what makes Montepulciano special. The guide explains the production of Nobile wine, helping to deepen appreciation during the tasting.

Pienza’s Small-Town Brilliance and Local Flavors

The tour continues to Pienza, the capital of the Val D’Orcia, famous for its Renaissance architecture and charming streets. The 45-minute walk through the historic center includes visits to Pienza’s key sites, offering sweeping views of the countryside. The town’s medieval and Renaissance features make it a favorite photo stop.

Visitors have time to enjoy the local atmosphere, and the guide shares insights into Pienza’s history. Though no specific tasting is listed at Pienza, the sightseeing and scenery provide a relaxed yet enriching experience.

The Second Day Begins in Siena’s Artistic Heart

The second day starts with a 1 hour 30-minute visit to Siena, where the Duomo, Piazza Il Campo, and Public Palace showcase the city’s medieval richness. Entry to the Duomo is included, allowing a close look at Siena’s stunning Gothic architecture. The third highest tower in Italy, Torre del Mangia, adds to the skyline.

This stop emphasizes art, history, and local culture, with enough time to explore at a leisurely pace. The guide’s commentary enhances understanding of Siena’s unique Palio di Siena traditions.

San Gimignano’s Medieval Skyline and Vernaccia Tasting

Next, the group visits San Gimignano, known as the “Manhattan of the Middle Ages” for its towers. The 1-hour 30-minute stop includes visits to Piazza Sant’Agostino, the Duomo, and Piazza Cisterna. Tasting Vernaccia di San Gimignano wine is a highlight, complemented by Gelateria Dondoli’s renowned gelato, considered a world champion.

This part of the tour offers stunning views, historic streets, and local flavors, making it a favorite among visitors for its charm and delicious ice cream.

Chianti’s Heritage and Casa Emma’s Wine Cellar

The final stop is Castellina in Chianti, with a 30-minute visit to Via delle Volte and the Chianti Classico fortress. The group then proceeds to Casa Emma, where they taste Chianti and Supertuscan wines, along with olive oil and wine vinegar. The 1 hour 15-minute tasting at Casa Emma provides insights into Sangiovese grapes and local production methods.

This experience wraps up the tour with a focus on wine appreciation and the Chianti region’s countryside charm. The ability to explore Chianti at your own pace with a private driver adds comfort and flexibility.

Accommodations and Included Comforts

Overnight stays are arranged at an agriturismo, offering a chance to relax amidst Tuscany’s natural beauty. The tour includes breakfast, all fees and taxes, and WiFi on board, making logistics smooth and enjoyable. Since lunch is not included, travelers should plan for meals during free periods.

Flexibility and Cancellation Policies

The tour offers free cancellation up to 24 hours in advance, providing peace of mind for travelers. Confirmation is received at booking, and the experience is suitable for most travelers, with most participants able to join.

Who Will Appreciate This Tour Most?

This two-day Tuscan tour suits those seeking a rundown of Tuscany’s hill towns, wine estates, and cultural landmarks. It’s especially ideal for travelers wanting to avoid driving and enjoy a personalized, guided experience**. The focus on wine tastings, combined with visits to famous towns, makes it perfect for wine enthusiasts and history lovers alike.

Final Thoughts on the Tuscany Discovery Tour

This private guided tour balances sightseeing, culture, and wine tasting in a way that few other experiences can match. The inclusion of specific wineries like Contucci and Casa Emma, along with stops at Montalcino, Montepulciano, and San Gimignano, provides a well-rounded taste of Tuscany’s diverse heritage.

The comfort of private transportation and expert guides elevate the experience, making it suitable for first-time visitors or those looking for a convenient way to explore key Tuscan highlights. While lunch is not included, the tour’s structure encourages exploring local eateries or enjoying the surroundings during free time.

This tour offers authentic encounters with Tuscan towns and wines, delivering lasting memories of this beautiful region—especially for those eager to explore the best of Tuscany in just two days.

Frequently Asked Questions

Is this tour suitable for people with mobility challenges?
Most stops involve walking through historic towns, so some walking is required. Check with the provider for specific accessibility information.

How many wineries are included?
Two wineries are part of the experience, including Contucci Cantine and Casa Emma.

Can I customize the itinerary?
This is a private tour, so guides may tailor some aspects to your interests, but the core stops are fixed.

What is included in the price?
The price covers all fees and taxes, private transportation, air-conditioned vehicle, WiFi, two wine tastings, and breakfast at the agriturismo.

Is lunch included?
No, lunch is not included, giving flexibility to choose local eateries during free time.

How far in advance should I book?
Most bookings are made about 41 days in advance, ensuring availability.

What is the best time of year for this tour?
While not specified, most travelers prefer visiting Tuscany in favorable weather, typically spring through early fall.

What makes this tour stand out?
The combination of towns, wineries, and cultural sites with private transportation and personalized guidance creates a rich, hassle-free experience.

Can I cancel if my plans change?
Yes, full cancellation is available up to 24 hours before the tour, with no penalty.

How long are the stops at each location?
Stops range from 30 minutes at Piombaia winery to 1 hour 30 minutes in Siena and San Gimignano, allowing ample time for sightseeing and tasting.