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

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta, salami, cheese, and extra virgin olive oil.
Between tastings, stop at the medieval village of Monteriggioni for free time to explore or relax before returning comfortably to Siena.

Hidden Castles & Chianti Wine Experience– Small Group

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 which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you need to enjoy your trip with a five-star service. This experience will give you the advantages to truly enjoy the tour instead of the big bus tours where you have to follow a strict schedule. So relax while we discover the history of the Chianti region, visit the Fortress of Montalcino or upgrade your tour and taste Brunello wine in a boutique winery family owned.

You will taste amazing wines and delicious Tuscan products like Pecorino cheese, Bruschetta, Salame and Virgin olive oil.

You will also enjoy a private tour of the historic cellar and learn about the wine production process in a charming atmosphere . All the tour is performed by a licensed tour guide that will make you feel like a local.

Small group Chianti Classico & Brunello wine region 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

To fully experience la "Bella vita", you need to get out of the city. 
Taste the local wines & tour the cellars of select family-run, boutique vineyards with high-quality production.
Get picked up at the designated meeting point & venture into the Tuscan countryside with a small group and a local guide

Together you'll visit two vineyards in the rolling hills of Tuscany, both boutique wineries specializing in Montepulciano reds. From there you'll head to the enchanting Medieval town of Montepulciano, where you'll visit a first historic winery with underground cellar or a family run boutique winery! 

Lunch will take place in yet another, Nobile di Montepulciano winery, where you can enjoy traditional Tuscan delicacies in a really complete lunch (3 Courses) paired with the great wines produced in this region since the XVI Century.



Full-Day 2 Wineries Tour in Montepulciano with Tasting and 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

Explore the town of Montalcino and uncover the fascinating history behind its imposing stronghold, all while tasting the exceptional flavors of its world-renowned wines, on a half-day cultural tour. Immerse yourself in the breathtaking countryside views, allowing your senses to be enchanted by the surrounding beauty, and relish a carefully curated wine tasting experience, as you join us on this guided 5 hour excursion, promising an unforgettable exploration of this enchanting region.

Signature Brunello di Montalcino Wine Tour from Siena

Have a special night in Chianti's vineyards, enjoying dinner under the stars. Visit the farm's wineries for wine tastings, and savor local dishes in a cozy setting with candles. Have a BBQ with fresh farm food and taste Chianti's red wine. Allow the warmth of the barbecue, the fragrances in the air, and the essence of the grapevines to elevate your dining experience. The charming rural setting ensures a relaxing evening in the vineyards located in the stunning Chianti region.

Sunset Summer Dinner Among the Vines – Small Group from Siena

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

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their environment, biological cycle, and how truffle dogs are trained.

The meeting point is at our office in Castellina in Chianti, from where the experience begins. Our experienced hunter and his dog will lead you through the forest in search of this "edible gold," making for an entertaining and enriching morning.

The adventure continues at a local farm, where you will enjoy a traditional Tuscan lunch featuring the truffles you've found, paired with other local specialties. This is a unique opportunity to connect with the land, its flavors, and centuries-old traditions.

Private Truffle Hunting in Chianti

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 enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti's rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Chianti Half Day Wine Tasting Tour from Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it's simple use as a vehicle. Ideal both on city's tiny alleys and on the famous country-side windy roads. 
We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can.
The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines.
The meeting point will be in our office in Castellina in Chianti.


Private Vintage Fiat 500 tour in Chianti

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

Tuscany is one of the great food and wine destinations of Italy, and, indeed the world. The scenery is unbelievably beautiful with large tracts of agricultural land, including wheat fields, vineyards and olive groves, placed on rolling hills, dotted with cypress trees and criss-crossed by white gravel roads.
So just imagine this: An unforgettable week in southern Tuscany, tasting some exceptional wines, learning how to cook like an Italian, visiting some spectacular medieval towns and enjoying sumptuous gourmet meals. All while staying in luxurious accommodation in the beautiful Val d'Orcia World Heritage area while in the company of other like minded people. 
Our Food & Wine Experiences are unique as they consist of small groups ensuring a more personalised and intimate experience.

8 Days Tuscan Food and Wine Experience Shared Tour

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

Chianti and its ancient roads reconnect with the spiritual, archaeological, and rural traditions of this land. There are few places in the world like Chianti, where the natural landscape merges with millenary history. Several footpaths lead you along routes dating back to the Middle Ages, which left deep and well-preserved traces among these hills.

Together with a local hiking guide, you will have the chance to walk along these age-old paths, once considered strategic routes that, for centuries, attracted pilgrims to this sublime territory. This experience is one of the best ways to enjoy Tuscany's landscape in full harmony with nature. Simply slow down and immerse yourself in it.

Different hiking levels and routes are available, making this outdoor activity suitable for everyone. To complete the experience, you will enjoy a typical Tuscan lunch paired with wine.

The meeting point is at our office in Castellina in Chianti.

Private Hiking in Chianti

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.

Bus Tours in Siena