Top Siena Private Sightseeing Tours

Entry ticket and a self-guided audio tour of Siena are available via the WeGoTrip app. You’ll receive an email with a link to download the app, which includes your ticket and a digital guide with maps, photos, scripts, and audio commentary. Please download the tour in advance. (!) Note: The cathedral ticket is included in the app, but the in-cathedral audio guide uses a separate app. After visiting the cathedral, explore Siena’s cobblestone streets. See Piazza del Campo with its iconic shell shape, Palazzo Salimbeni, Accademia Musicale Chigiana, and finish at the Medici Fortress, a historic cultural landmark. Along the way, discover stories of elegant fountains, renowned Renaissance painters, and the world-famous academy, immersing yourself in the city’s rich history and culture.

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.

Exploring Siena with kids has never been so much fun! Your kid-friendly guide will introduce your family to Saint Catherine of Siena—one of Italy’s most important saints—with tales that spark imagination and curiosity. Then, make your way through the city’s narrow streets toward Piazza del Campo, where the legendary Palio horse race takes place, and your guide will share the thrilling traditions, pageantry, and playful rivalries. Nearby, you’ll discover Fontebranda, one of the oldest fountains in the city, and you’ll pause outside the Torre del Mangia. Even without climbing it, this tall bell tower inspires awe—and laughter—when kids learn the funny origin of its name. The tour concludes with a visit inside the magnificent Siena Cathedral. Its bold black-and-white marble stripes, intricate floors, and awe-inspiring sculptures are the perfect finale to your family’s journey. This family-friendly tour is a wonderful way to experience Siena’s beauty, history, and legends together.

Have you noticed that there are certain times of the day when art cities are overrun by tourists or extreme heat? Well, this tour is designed specifically for the visitors who want to avoid both! It is a private 1 and ½ walking tour that focuses on the city’s main landmarks during quieter times. You can choose between a morning slot (7:00 AM to 10:00 AM) or an evening slot (6:00 PM to 9:00 PM). The tour covers the city's key sites, such as Piazza del Campo—where the twice-yearly Palio horse race takes place—and Piazza del Duomo, featuring the magnificent Cathedral of Santa Maria Assunta. We will also walk along Via Banchi di Sopra, once a pilgrimage route to Rome. In short, like all brief tours, we will visit the most important sights... but at a more relaxed pace and with the night street lights on!

Discover Siena on an immersive walking tour through one of Tuscany’s most enchanting medieval cities, a UNESCO World Heritage Site. We discover the historic Palazzo Salimbeni, headquarters of the Bank Monte dei Paschi, and the city’s deep financial and cultural heritage. Continue through narrow medieval streets filled with artisan shops and local flavors. Visit the spectacular Piazza del Campo, famous for its shell shape and the legendary Palio horse race held twice a year. Admire the Palazzo Pubblico, Torre del Mangia, Loggia della Mercanzia, and Fonte Gaia while learning about the traditions of the city’s Contrade. The journey continues through charming alleys where you can find Tuscan specialties such as local wines and salami. The tour concludes with exterior views of the stunning Baptistery of St.Giovanni and the magnificent Duomo of Siena, masterpieces of white and black marble that define the city’s skyline. An experience that blends history, culture, and authentic Tuscan life

Explore Quaint Villages and Timeless Landscapes Our journey will take you off the beaten path, winding through both lesser-known hamlets and iconic landmarks alike. Immerse yourself in the rich history and culture of each village we visit, from hidden gems tucked away in the countryside to well-known destinations steeped in tradition. Capture Every Moment, Embrace Every View As we traverse the rolling hills and winding roads, there will be ample opportunities to pause and soak in the panoramic views. Experience the Joy of Open-Air Travel Feel the sun on your face as you cruise through the Val d'Orcia on your Vespa. This isn't just a tour – it's an immersive journey into the heart of Tuscany's natural beauty. Let the open road be your guide as you embrace the freedom of outdoor exploration. Don't Miss Out on This Unforgettable Experience Join us for a Vespa adventure like no other and discover the magic of Val d'Orcia in a whole new way.

Hop on a full-day private tour to Florence and San Gimignano from Siena. Your adventure kicks off with a drive from Siena to Florence to explore the city center. Take a guided walking tour of the historic center and see key landmarks, including the Duomo, the Uffizi Gallery, and the Ponte Vecchio. Then, it's off to experience the medieval town of San Gimignano, known as the "medieval Manhattan."

Explore the mesmerizing medieval cityscapes of Siena, “the ideal embodiment of a medieval city” described by UNESCO, composed of romantic hilly streets, vibrant atmosphere, rich culture, and numerous significant historic and architectural landmarks, including Salimbeni Palace – the headquarters of the oldest bank in the world in continuous operation, the Sanctuary House of Saint Catherine – the birthplace of a globally influential Catholic Saint, the pristine 11th-century Fontebranda with its sophisticated system still in use, the Gothic treasure of Siena Cathedral and its unfinished successor, the elegant Loggia of Merchandise - the iconic early trading venue of the medieval city, and the charming Camp Square - one of Europe's greatest medieval squares.

Discover the medieval charm of Monteriggioni on a private luxury e-bike experience, ride scenic Tuscan roads, enjoy a curated lunch paired with fine wines, and end with an exclusive winery visit scheduled just for your group. More than a bike tour, this is a curated Tuscan experience for couples, families, and small groups seeking an authentic, relaxed, and elevated way to explore. Led by a professional local cycling guide, far from crowded routes, your ride is tailored to your pace, allowing you to fully enjoy the landscape and timeless atmosphere. Premium e-bikes ensure a smooth, accessible ride with minimal effort. The experience concludes with a refined lunch and wine pairing in a carefully selected winery, featuring a private dining room reserved for you and a private cellar visit without overlapping guests. A seamless Tuscan day blending cycling, culture, landscape, and fine wine — designed for comfort, privacy, and authenticity.

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style aboard a luxury NCC van, accompanied by a local guide who brings the history and culture to life. Siena: Stroll through the medieval streets of this UNESCO World Heritage city, marvel at the stunning Piazza del Campo, and visit the inspiring Cathedral. San Gimignano: This hilltop town will enchant you with its skyline of towers and artisan shops. Enjoy free time to explore the village. Monteriggioni: Step back in time in this perfectly preserved medieval village nestled among olive groves and vineyards. Its fortress walls and quiet charm will transport you to another era. No Tuscan journey is complete without indulging in its world-renowned flavors. You’ll be treated to an exclusive wine tasting experience at a local winery, sampling celebrated Chianti wines paired with regional delicacies like pecorino cheese, and cured meats.

This is an exclusive tour for you and your loved ones and, comfortably seated in the car you can enjoy the beauty of the places. In fact, we will see fascinating landscapes that are a little lost in time. In fact, the Maremma, in addition to being considered the new Eldorado for its powerful and elegant wines, offers wild and splendid landscapes. The typical local cuisine is Mediterranean. The people of Maremma are the most outspoken in Italy. Furthermore, the story I told will take us back in time to the Etruscans. As our ancestral ancestors did, you can, if you wish, take a thermal bath in the Saturnia waterfalls. New shower and toilet rooms available.

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.