Top Siena Sightseeing Tours in 2026

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair and finishes with a lunch of Tuscan dishes and wine.

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

Explore Chianti’s backroads and beautiful vistas while traveling in a private 4WD on this tour with hotel pickup. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste several Chianti Classico wines along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a traditional Tuscan lunch at a scenic family estate.

Explore Siena in a fun and kid-friendly way on this tour created for families with children. As you make your way through the city, your guide will engage young travelers with lively storytelling and riddles to uncover Siena’s secrets. Visitors of all ages will come away with deeper knowledge of local history, art, and traditions. This tour ends with a special surprise gift.

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets, we will talk about Palio and Contrade, noble palaces, famous painters, Francigena and illustrious characters. Towers, medieval houses, squares and ancient sources. Monte dei Paschi, the famous Duomo with its masterpieces, the Ancient hospital and the noble public palace. I wait for you for a pleasant and interesting private tour of the city of Siena

The Tuscan countryside is a premier hiking destination, but navigating unfamiliar trails and country roads on your own can be daunting. On this private hiking tour, explore the rolling hills and vineyards stress-free with a guide leading the way. Meet in Siena and transfer to the trailhead by minivan, setting off through the verdant countryside and past rustic villages. Take a break to relax over a classic lunch of Tuscan treats and then travel via minivan to San Gimignano for a stroll through town and along a stretch of the Via Francigena before the return ride to Siena.

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

Many of Italy’s most charming hill towns are a challenge to reach with public transport. This private day trip offers seamless round-trip transport, giving you time to explore Volterra and San Gimignano at your own pace. Enjoy free time in both towns, with lunch at a Chianti cellar accompanied by a tasting of five different wines.

The hills south of Siena are home to some of Tuscany’s most prestigious wines, but navigating the country roads can be a challenge. This private tour includes visits to three historic wineries in Montepulciano and Montalcino for tours, tastings, and lunch. Break up your cellar visits with a stop in Pienza for a pecorino cheese experience.

Explore Val d’Orcia, a UNESCO World Heritage site known for its stunning landscapes, art, and rich food traditions on this private tour. Visit Montalcino, home of the renowned Brunello wine, where you'll enjoy a guided winery tour and lunch. Then, head to Montepulciano, a medieval city with Renaissance palaces and sweeping valley views, famous for its Vino Nobile wine. Enjoy wine tastings in both towns while taking in their historical and scenic beauty.

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.

Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Nobile. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.

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. Pick up and drop off from your accomodation in Siena included.

Experience a side of Italy rarely available to visitors when you take a cooking class in the Chianti wine region. During your private session, discover the secrets of Tuscan cuisine, from sauces to tiramisu. After dining on the food you just learned to make, continue on to a vineyard for a complimentary wine tasting and pairing lesson. Round-trip transport from Siena is included for your convenience.

That's a short but exhaustive tour that touches the most important places of the beautiful city center of Siena.

Discover the architecture, art, and culture of Tuscany's medieval era on this private tour from Florence. Journey to the city of Siena and visit its most-important landmarks, including the 13th-century cathedral. Afterward, travel to San Gimignano to understand why the small city is known as the "Manhattan of the Medieval Ages."

Siena is one of Tuscany’s most picturesque medieval towns and this private walking tour is ideal for first-time visitors or those short on time. Take in the highlights of the UNESCO-listed center, stroll around lively Piazza Del Campo, and admire landmarks such as San Domenico Basilica, Palazzo Tolomei, and Cathedral of Siena.

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.

Discover the most beautiful places in Siena together with our professional photographer and our tour leader who will take you wonderful photos at Piazza San Domenico in the historic center, the Duomo and Piazza del Campo You will not be a passive spectator, but you will be the center of attention, free to enjoy the city without hindrances such as cameras and various devices. Once the tour is over the photographic material will be shared telematically already edited.

Discover the rich history and artistry of Siena with the OPA SI Pass, granting you access to the iconic Siena Cathedral Complex. This ticket includes entrance to remarkable sites like the Baptistery, Crypt, and Museo dell'Opera, showcasing masterpieces by renowned artists such as Michelangelo and Donatello. Enjoy the panoramic views from the Duomo Nuovo and delve beneath the Cathedral with the immersive 'Paths of Light' tour. Valid for three consecutive days, the OPA SI Pass saves you 50% on individual admissions while allowing you to explore at your own pace. Perfect for art enthusiasts and history lovers alike. 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

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint Francis in Assisi's Basilica. Stop for lunch in an intimate, local restaurant/farmhouse, for a gourmet meal with a glass of Montefalco Red or Sagrantino ready at hand for a toast, and experience their local extra virgin olive oil production. After lunch delight in Deruta, where you will encounter extraordinary ceramics and have the chance to visit Ubaldo Grazia, the world's most ancient majolica factory

The audio guide is a convenient mobile companion for a self-guided walk in Siena. The tour is designed specifically for getting to know the city in a relatively short time of 1.5–2 hours. Follow the route on the in-app map to walk from Piazza del Campo to the Medici Fortress, passing by the city’s main landmarks. Highlights include: Siena Cathedral, Fonte Gaia, Palazzo Chigi-Saracini, Galluzzi Arches, Fontebranda Fountain, House of Saint Catherine of Siena. The tour includes 26 points of interest. All stories are written by professional journalists and historians with a touch of humor and a love of travel. After you download the tour, you can run it offline in the app. We recommend using headphones to hear the audio guide clearly. Enjoy engaging stories and legends as you move at your own pace, without the need to follow a tour group. At any moment, you can stop to rest at a café or turn into a picturesque alley, and then continue your walk around the city.

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition to it, this tour has an Arts footprint. We'll lead you through some hidden sculptures, located throughout the landscape, as a warm up to our stop at the Chianti Sculpture Park, where you'll visit some contemporary sculptures and installations. We'll build on to the arts experience by stopping at the hamlet of Scopeto, where the film "Letters to Juliet" has been shot. Least, but not last, it will be wine time right after at the Scopeto Winery, where you can further develop your reconnaissance of the territory by tasting one of its maximum expression: the Chianti Classico. We then, climb back to our comfortable ebikes to return to Siena

Hop aboard our eco-friendly electric tuk tuk and embark on a panoramic journey around Siena. As you wind your way through the picturesque hills surrounding the city, you’ll be treated to breathtaking views of Siena’s iconic landmarks and rolling countryside. Experience a tasteful "Aperitivo" and savour authentic Tuscan delicacies and a glass of fine wine. Please note, tours are normally in group