Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d'Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm!

Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.

Small-Group Montepulciano and Pienza Day Trip from Siena

Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round the Fortress of Monteriggioni, explore the UNESCO World Heritage-listed town of San Gimignano, and visit an alabaster workshop in Volterra. Enjoy a delicious lunch on a small Tuscan farm and spend time at your leisure exploring these rustic hill towns that are steeped in rich Italian history.

Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.

Small-Group San Gimignano and Volterra Day Trip from Siena

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni's perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included.

(*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the region. With your expert guide, visit Castello di Brolio, renowned as the birthplace of Chianti wine. Sample the esteemed Chianti Classico wine, enjoy an authentic Italian lunch at a Tuscan wine estate and tour the cellars to learn about the passion behind this traditional wine directly from the producer. Enjoy some of the region's best wines directly at the winery. 

Numbers are limited to eight people on your small-group trip, ensuring you'll receive personalized attention from your guide.

Small-Group Chianti Trip with Wine Tasting from Siena

Spend an unforgettable day exploring Italy's iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards of Chianti, taste the famed Brunello di Montalcino, and savour local snacks, olive oil and balsamic vinegar – all in a comfortable small-group vehicle

San Gimignano, Chianti, and Montalcino Day Trip from Siena

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.

Small-Group Chianti and San Gimignano Sunset Trip from Siena

This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you the advantages to truly enjoy the experience and not have to be in a crowded bus and follow a strict schedule . 

We will visit 2 beautiful boutique family owned wineries in a relaxed atmosphere and meeting the locals.

You will taste top rated wines like Chianti Classico & Brunello di Montalcino while enjoying beautiful views and learning all the secrets of the best wine regions in the world.

VIP Chianti, Brunello wine & Pienza with lunch From Siena

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. 

Start this full-day tour with a lesser-known boutique vineyard with high-quality wines. You will taste all their full-bodied Brunello reds that make this region every wine lover's dream. 

After your first tasting, take some time to explore the hilltop town of Montalcino. Explore the medieval fortress and Romanesque churches, stroll through the shops of artisan crafts, or simply enjoy the breathtaking panorama of the Tuscan countryside.

At the second winery, you will pair the exquisite Brunello with a special lunch featuring local specialties, meeting the winemakers who make the magic happen. Enjoy! 

Pick-up & Drop-off at the designated meeting point
2 wine tastings at boutique wine cellars
Lunch with wine pairings & local specialties
Visit Montalcino
Small group: limited to 8 guests

English-speaking DRIVER GUIDE 
MERCEDES MINIVAN

Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion of rich history and flourishing countryside. Allow yourself to be mesmerized by the sensational beauty that surrounds you, as you savor the exquisite, locally produced wines, each sip a proof of the unforgettable memories you'll create during your trip.

Siena: Best of Tuscany Wines & Lunch in Montepulciano small group

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience.

Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. 
Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery.

Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

DEPARTURE GUARANTEED!

Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine!

Please note that from November to April I cannot guarantee the restaurant with view, as stated in the inclusions.

The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters. 

There you will be surrounded by impressive views, art, culture, amazing wine and delicious food!

Your semi private tour will be on board of a premium minivan with an English speaking driver, air conditioning and free water.

WHY CHOOSE ME?

Secure bookings, Guaranted Departures!

48 hours Cancellation policy, best rates guaranteed!

Group of maximum 8 people.

Val D'Orcia Tour From Siena Montalcino Pienza and Montepulciano

Depart from Siena and enjoy a full-day tour to Pisa, San Gimignano, and Chianti.
Savor a traditional lunch at a Chianti winery with antipasto, fresh pasta, dessert, and a tasting of 3 local wines.

Pisa, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting

Explore the medieval charm of Lucignano and the artistic treasures of the city of Arezzo. Enjoy a farm-fresh Tuscan lunch with wine before visiting Cortona, a hilltop gem with breathtaking views and ancient history, all guided by an expert in the region's culture and heritage.

Small-Group Arezzo and Cortona Day Trip from Siena

Explore the artistic heart of Tuscany with this Florence Walking Tour from Siena. Experience a scenic train ride to Florence, where you'll discover iconic landmarks such as the Cathedral of Santa Maria del Fiore, Piazza della Signoria, and the historic Ponte Vecchio. This guided tour brings the city's rich history to life, revealing hidden gems and engaging stories about the Renaissance. Enjoy free time to wander and soak in the vibrant atmosphere of Florence, making this a perfect day out for art lovers and history enthusiasts alike.

- Scenic train journey from Siena to Florence included
- Guided walking tour featuring major landmarks and hidden gems
- Free time to explore Florence at your own pace
- Ideal for those comfortable with walking and stair climbing

Florence Walking Tour from Siena with Train Tickets Included

Explore Florence's artistic heritage on this comprehensive 11-hour tour from Siena. Visit the iconic Accademia Gallery to see Michelangelo's "David," followed by a guided walking tour through the historical city center, showcasing the magnificent Florence Cathedral and the famous Ponte Vecchio. Conclude your journey at the Uffizi Gallery, home to masterpieces by Botticelli and da Vinci. With expert guidance and insights into the Renaissance, this tour offers a rich cultural experience filled with history and art appreciation.

- Full-day guided tour from Siena to Florence, lasting 11 hours
- Includes entry to Accademia Gallery, Cathedral, and Uffizi Gallery
- Small group size with a maximum of 14 participants
- Comfortable walking required; headphones provided for larger groups

Highlights of Florence Day Tour from Siena

Our exclusive experience invites you to uncover the secrets of the wine harvest — from learning traditional picking techniques to tasting wines straight from the barrel. Conclude your day with a harvest lunch perfectly paired with estate wines, and finish on a sweet note with dessert accompanied by freshly pressed grape juice.


Brunello Harvest Experience in Tuscany

Discover Florence's iconic Duomo Complex, including the Cathedral, Baptistery, and the Opera del Duomo Museum, all with a licensed guide. This 8-hour and 40-minute tour offers a deep dive into Renaissance art and architecture. Enjoy round-trip train tickets from Siena and insightful commentary through HD audio systems. Walk in the footsteps of great artists like Michelangelo and Giotto, and explore masterpieces housed in the Duomo Museum. Perfect for art lovers and history enthusiasts, this tour provides a unique opportunity to learn about Florence's cultural heritage.

- Full-day tour from Siena to Florence's historic Duomo Complex
- Licensed guide and earphones for groups of more than 4 participants
- Includes round-trip train tickets and official entrance fees
- Explore masterpieces from the Renaissance at the Duomo Museum

Explore the Duomo Complex Guided Tour from Siena

Discover Siena's perfectly preserved medieval splendor with our self-guided audio tour app, allowing you to explore this Tuscan jewel at your own pace. Begin at the magnificent Piazza del Campo, the shell-shaped square that hosts the legendary Palio horse race and remains the heart of Sienese civic life after seven centuries. Marvel at the soaring Torre del Mangia and the Gothic grandeur of the Palazzo Pubblico, then ascend to the heavenly Duomo where Pisano's pulpit and the Piccolomini Library showcase Renaissance mastery. Wander through the contrade neighborhoods where medieval rivalries still define local identity, their fountains, flags, and parish churches marking territories unchanged for centuries. Discover the Pinacoteca's golden altarpieces and the Basilica of San Domenico where St. Catherine's head is reverently preserved, then lose yourself in the winding vicoli that reveal unexpected piazzas and artisan workshops. 

At Your Own Pace: Discovering Siena & Tuscany

Explore Florence's artistic treasures with a guided tour of the Uffizi Gallery on this day trip from Siena. Travel through the picturesque Tuscan countryside by train and marvel at masterpieces by renowned artists like Botticelli, Leonardo da Vinci, and Michelangelo. Your expert guide will share captivating stories behind each artwork, enriching your understanding of the Renaissance. After the tour, enjoy free time to further explore the gallery or the enchanting city of Florence at your leisure.

- Duration: 7 hours and 30 minutes, including train travel
- Guided tour of Uffizi Gallery with skip-the-line entry
- Free time in Florence to explore at your own pace
- Includes round-trip train tickets; van pick-up available for groups of 6 or more for an additional 20€.

Siena to Florence Uffizi Gallery Guided Tour

Explore the artistic wonders of Florence with a guided tour of the prestigious Accademia Gallery. This tour allows you to marvel at Michelangelo's iconic statue of David and other masterpieces, all while benefiting from the insights of an expert guide. Enjoy a comfortable journey with included train tickets from Siena to Florence, giving you free time to explore the city at your leisure. With a maximum of 9 participants, this semi-private experience ensures a personal touch as you traverse the streets of Florence and delve into its rich artistic heritage.

- Full-day guided tour from Siena to the Accademia Gallery in Florence
- Admire Michelangelo's David and other significant artworks
- Includes train tickets for easy transportation to Florence
- Maximum group size of 9 for an intimate experience

Accademia Gallery Guided Tour from Siena with Train Tickets

Experience the best of Tuscany on this small-group tour departing from Siena. Travel through the scenic Chianti hills to Castellina in Chianti, then explore medieval villages like Monteriggioni and Certaldo at your own pace.

Join a hands-on cooking class and enjoy a full Tuscan lunch, then visit a local wine estate to taste traditional wines. Relax on a comfortable shuttle back to Siena after a day filled with stunning landscapes, local flavors, and authentic Tuscan culture.

From Siena: Tuscany Villages Tour with Lunch & Wine

Visit the iconic Santa Maria del Fiore Cathedral in Florence on this guided tour from Siena. With a licensed guide, explore the stunning architecture and rich history of one of Italy's most famous landmarks. Receive a 3-day valid ticket to visit the Baptistery, the Opera del Duomo Museum, and the ancient basilica of Santa Reparata independently.

- 1-hour guided tour of the Florence Duomo Cathedral
- Round-trip train tickets from Siena to Florence included
- Free time to explore Florence after the tour

Florence Duomo Cathedral Guided Tour from Siena

Experience the highlights of southern Tuscany on a full-day small group tour from Siena through the rolling landscapes of the Val d'Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery.

Your first stop is Montepulciano, where you'll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine.

Continue to Pienza, the "ideal Renaissance city," and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops.

In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy's most celebrated wines.

Full-day Tours in Siena