Top Siena Sightseeing Tours in 2026

Immerse yourself in a 5-hour wine tour from Florence that promises a journey packed with adventure, luxury, and wine. Departing from your accommodation in Florence, head straight towards San Gimignano, a stunning medieval town in the country that boasts views of vineyards, olive groves, and rolling hills. Once in town, you'll have an hour of free time to shop at local artisan shops or take pictures of the intricate architecture of this ancient town.

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 timeless beauty of Tuscany on a full-day tour visiting the medieval towns of Siena, Monteriggioni, and San Gimignano with the option of adding a visit to a local winery in the heart of the Chianti. Experience the enchanting atmosphere as you travel through the Tuscan countryside, characterized by rolling hills, vineyards, and olive groves. Wander through ancient streets, admire stunning architecture, and soak in the authentic character of three iconic destinations at a leisurely pace. - Full-day exploration of Tuscany’s medieval towns: Siena, Monteriggioni, and San Gimignano - Relaxed pace allowing for in-depth discovery of each town - Scenic journey through picturesque landscapes filled with vineyards and olive groves. POSSIBILITY TO ADD A STOP AT A WINERY. - Experience Tuscany’s rich history and charming atmosphere firsthand

Siena lovers, you will get the chance to breathe the atmosphere of the life of the Contrada and the Palio of Siena! An exclusive opportunity! An exciting experience lived with its protagonists: the Sienese people: vising the Museum and the Church of the Contrada Our guide will also lead you through the Piazza del Campo, where the most famous Palio in the world takes place every year on July 2nd and August 14th. We will also visit the Duomo of Siena, a gem set in a jewel city! We will continue to move into the world of the purest tradition with a tasting of typical Sienese sweets: Panforte, Ricciarelli and Cavallucci accompanied by Vin Santo del Chianti. These products, famous all over the world, maintain a high quality offered to the public in the past hundred years! The family of singer Gianna Nannini has been producing these sweets for generations and iat Caffè Nannini twe will stop and taste these specialities.

IF YOU ONLY HAVE ONE DAY IN LIVORNO, THAT'S THE BEST TOUR YOU CAN DO, OUR VEHICLES REACH ANY RESTRICTED PLACE AND WE TAKE OUR CUSTOMERS INSIDE THE HISTORICAL CITY CENTER

Embark on a delightful journey through the picturesque Chianti region on a private tour from Siena. Combining regional cuisine, local history, and iconic landscapes, this excursion enables you to get the complete Tuscan experience in a single day. With highlights including a family-run winery, Monteriggoni Castle, and the hill town of San Gimignano, this robust, well-paced itinerary lets you savor your limited vacation time without feeling hurried.

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!

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."

Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.

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.

Enjoy a private, exclusive tour with your own local guide. Embark on a captivating walking tour through Siena’s most cherished sites, immersing yourself in the heart of this historic city. Start your adventure at the iconic Piazza del Campo, home to the towering Torre del Mangia and the majestic Pubblico Palace, which encapsulate the architectural brilliance of medieval Italian city-states. Just a stone’s throw away, delve into the eerie world of the Museum of Torture and uncover a darker slice of Siena’s history. The highlight of your tour will be the visit to the Duomo di Siena, a stunning example of Italian Gothic architecture and a repository of art and history. This tour promises a comprehensive glimpse into the rich tapestry that makes up Siena, blending its awe-inspiring beauty with profound historical narratives. Perfect for history buffs and art lovers, this journey through Siena’s best spots will leave you enriched and inspired.

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

Discover Siena through a unique immersive audio experience, among medieval mysteries, spirituality, folk legends and timeless traditions. With the audio guides of i-tourist.it you can explore the city in total autonomy directly from your smartphone, without groups and without fixed times. Stroll through Piazza del Campo, Siena Cathedral, Fontebranda and the ancient medieval alleys listening to engaging tales about Palio, Contrade, knights, esoteric symbols and hidden stories of the city. The experience also includes deep guided meditations in the most suggestive places of Siena, perfect for relaxing and connecting with the authentic soul of the city. Ideal for those who love History, Culture, Mystery, Wellness and Emotional Trips off the classic tourist routes. Experience Siena slowly, at your own pace, letting yourself be guided by unforgettable atmospheres, emotions and stories.

Discover the treasures of the Civic Museum in the Public Palace, superb example of Gothic architecture and symbol of the city of Siena. It preserves beautiful works of painting and sculpture, along with extraordinary frescoes by the Sienese school of painting such as the Maestà and the Portrait of Guidoriccio da Fogliano by Simone Martini, and the Cycle of Good Government and the Cycle of Illustrious Men. IMPORTANT: If the time slot indicated by the customer is no longer available, the museum will confirm the first available time slot closest to the indicated time

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.

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.

Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

Experience wellness in a historic Medici Villa overlooking the Val d'Orcia: panoramic thermal pools, natural 42°C waters, waterfall, and hydromassages in the Tuscan landscape.

After Reservation, the tour starts at the rental point with the collection of e-bikes and the activation of virtual navigation. The circular route is about 23 km long and has 140 m of positive elevation gain: medium-easy level. It starts from Alberese and crosses the Maremma Park to the coast, alternating paved roads, bike paths, trails and short stretches of singletrack. The Listing is almost flat, but the natural sections require a minimum of Guide confidence. The route crosses fields, Mediterranean scrub and centuries-old olive trees, then reaches the Torre di Collelungo, an ancient fortification overlooking the sea. In Marina di Alberese you can stop at Ristoro La Viola to buy water, a snack or take a break near the beach. The trail continues towards the mouth of the Ombrone, among reeds, dunes and environments rich in fauna. The return to Alberese completes a tour of protected nature, history and coastal landscapes.

Discover the beauty of Siena on a private walking tour through its most iconic landmarks, where medieval charm, art, and spirituality blend in perfect harmony. Your journey begins at Piazza San Domenico, closely tied to the life of St. Catherine, Siena’s patron saint. Just a short stroll away lies the Santuario Casa di Santa Caterina, a peaceful complex built around the birthplace of the saint. Nearby, you’ll come to Fontebranda, one of Siena’s oldest fountains. Your walk continues into the beating heart of the city: Piazza del Campo, a breathtaking shell-shaped square often considered one of Europe’s finest. Lined with graceful palaces and crowned by the Palazzo Pubblico and the Torre del Mangia, this is the stage for the world-famous Palio horse race. No visit to Siena would be complete without exploring the Duomo, a Gothic masterpiece adorned with black-and-white marble stripes, richly decorated interiors, and priceless works of art by masters such as Michelangelo.

Let our local guide guide you to discover the irresistible city of Siena, unique for having maintained its unmistakable medieval style intact. The main foundation of Siena's history, customs and popular traditions is the Palio, a horse race that takes place in the city twice a year, an event of great importance to the Sienese, who divide their supporters into contrade (districts) rich in legends, fervour and ancient symbols. The main attractions that our guide will show you during the tour are the splendid Piazza del Campo, with its characteristic shell shape, the majestic Palazzo Pubblico, the Torre del Mangia and the Fonte Gaia, a model of Renaissance sculpture. No less important, strolling through the alleyways of the centre, you will reach one of the most beautiful cathedrals in Italy, the Duomo di Siena. There are also alleys, narrow streets, ancient palaces, artisan shops, wineries and the many shops of the typical sweets of Siena: panforte, ricciarelli, cavallucci.

Fly the sweet hills and vineyards of Tuscany with a hot air balloon flight through the Val d'Orcia. Discover the magic of flight through the energy of the wind and fire. Get at an altitude of about 2000 feet and beyond, every day nature leads us to discover new landscapes. Surprising your family with a fantastic and unique tour.

Live a unique experience between history and flavors: enter the heart of the Monastery of Monte Oliveto Maggiore and discover the monks' handicraft products, from wines to fine oils. A food and wine journey that combines tradition and authenticity in one of the most beautiful and suggestive places in the world according to National Geographic.

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!