Top Siena Car Tours in 2026

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at boutique wineries in Chianti and Montalcino on this small-group tour from Siena. All transport is included for a hassle-free experience, with free time to explore Pienza. Sample top Chianti, Brunello, and Super Tuscan wines, and relax over a Tuscan lunch featuring local specialties.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

Siena, a medieval city rich in history and spirituality, is one of the most fascinating destinations for those who wish to have a unique religious and cultural experience. On this tour, accompanied by an experienced Catholic guide, you will discover the heart of the Sienese faith through a visit to Siena Cathedral, one of the most beautiful churches in Italy, and the House of St. Catherine, the place that holds the memories of the city's patron saint.

Unlock the mysterious world of Tuscany's tasty truffles on this half-day private tour from Florence. Look for these black and white treasures using man and pup power as you learn all about these delicious delicacies from an expert hunter. Afterwards, enjoy a lunch featuring truffles and wine tasting (own expense) and experience nature with every bite while exploring this exquisite part of Italy.

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

Avoid the hassle of navigating the rural roads and trying to locate the small cellars in Tuscany’s wine country with this wine tour that includes round-trip transportation. Stop for a tour and tasting at one or two scenic wineries near Siena before a lunch break. In the afternoon, visit cellars in Montalcino or the Val d’Arno to sample some of Tuscany’s most historic labels.

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

Embark on this Full-Day Private Montalcino and Montepulciano Wine Tour and indulge your senses in the heart of Italy's renowned wine country! Your day begins with a personalized, chauffeur-driven journey through the stunning Tuscan countryside, setting the scene for an unforgettable adventure. As you traverse the picturesque landscape, you will visit two prestigious wineries - in Montalcino and Montepulciano - each with its own unique charm and distinctive wines. Expert sommeliers and winemakers will guide you through tastings of exceptional Tuscan varietals, sharing their deep knowledge and passion for winemaking. Enjoy a delightful Tuscan lunch at a selected vineyard, paired with local specialties, perfectly complementing the wines you've tasted throughout the day. Don't miss this opportunity to create lasting memories on this Private Montalcino and Montepulciano Wine Tour, escaping the hustle of Siena for a day of indulgence and appreciation of Italy's vinicultural heritage.

This is the tour of the oldest Etruscan and Roman Maremma but remained intact over time. The thermal and healing spring attracts users from all over the world. Here you can breathe authenticity, history and rurality. Breathtaking views. Spectacular wines. The villages we will visit preserve the characteristics of Tuscany and its inhabitants still speak the ancient dialects. The Biodynamic, Biological company where we will have a picnic is truly an example of obsessive attention to traditions in respect of Nature! From the above you can enjoy a 360 degree view. Your basket includes: 2 basic wines, typical breads, 2 types of cheese, award-winning oil!

Optimize your travel time with this private transfer that breaks up the trip from Siena to Rome with stops in Orvieto and Civita di Bagnoregio to sightsee, shop, and dine. Enjoy hassle-free pickup at your hotel or other accommodation in Siena and enjoy views of the Tuscan countryside as you head south. Stop for free time to explore Orvieto and Civita before drop-off at your final destination in Rome.

Tour with a certified sommelier guide expert on Brunello. Discover Tuscany with local expert out of beaten path. learn the history of Brunello wine making and visit historical wineries.

Discover the history of the Chianti region, visit Montalcino's medieval fortress, and enjoy a scenic drive through Val d'Orcia on this small-group tour from Siena. Taste Chianti Classico and Brunello wines paired with Pecorino cheese, bruschetta, salame, and extra virgin olive oil. Explore the historic cellar and learn about the wine production process in a boutique family-owned winery.

In the heart of Tuscany and Chianti. Hills, vineyards, unspoiled nature. Intact medieval cities. Unforgettable atmospheres.

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.