Siena Travel Guides
Plan your trip to Siena with accurate, up-to-date travel guides created with local insight — skip tourist traps, save time, and enjoy the city like it’s meant to be experienced.
Siena Latest Travel Guides
View allDiscover the most recent travel guides for Siena curated by our community and experts.
Gentle 3-Day Siena for Seniors — Comfortable, Accessible, Cultural
Perfect for Seniors
Siena, Italy
Siena in Spring — 3-Day Fun & Vibrant Friends Getaway
Perfect for Friends
Siena, Italy
Siena — 3-Day Family-Friendly Spring Visit
Perfect for Families
Siena, Italy
Siena in Spring: A 3-Day Romantic Escape for Couples
Perfect for Couples
Siena, Italy
Easy-paced 2-day Siena for Seniors (May)
Perfect for Seniors
Siena, Italy
Siena in 48 Hours — Fun & Vibrant Friends Weekend
Perfect for Friends
Siena, Italy
Siena Popular tours and activities
View allDiscover and book popular tours and activities in Siena to make the most of your trip.
Half-day Private Walking Tour of Siena
Enjoy Siena with a professional guide who will let you discover the beauties of this UNESCO world heritage listed city. The itinerary will include the Duomo, Piazza del campo, The Church of San Domenico, The Public Palace, and dozens of small streets and neighbourhoods that make this city unique.
PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour
A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities• Our driver escort will pick you up at your location (hotel, B&B or private apartment) and take you on a drive through the sweet hills of Tuscany. • 1° stop in Montepulciano for a visit of the Historic Cellars. Here you'll find gigantic oak barrels, in which the famous Vino Nobile “rest”. We'll taste wines in 2 different cellars. • For lunch you will taste the famous pasta with "Pici", with delicious meat sauce (Ragù) and tuscan cold cuts • In the afternoon we will drive to Pienza, the town of the Pecorino cheese. The Pecorino is one of the best cheeses in Italy, especially the version 'sotto cenere' - ('under ashes') • Afterwards we will visit another farm in Montalcino. After visiting the spectacular vineyards and cellars, the tour will continue with 5 wine tastings in this prestigious winery, where the Brunello has been produced for generations. Take a look What to expect!
Excursión a la Toscana desde Roma con degustación de productos y vinos locales
La región de la Toscana no es famosa solo por su impresionante capital, sino también por los encantadores paisajes y pueblos que la conforman. Te invitamos a explorar las colinas del Chianti, un área llena de viñedos, bosques de encinas y castaños, y pintorescos pueblos medievalesExplora San Gimignano, Chianti, Siena y MonteriggioniIniciaremos nuestra aventura temprano por la mañana en tren desde Roma. La primera parada será Monteriggioni, un encantador pueblo en lo alto de una colina, rodeado por una muralla medieval intacta. Disfruta de tiempo libre para explorar sus calles y retroceder en el tiempo.Nuestra siguiente parada es Siena, una ciudad medieval que parece detenida en el tiempo. Pasearemos por sus calles y visitaremos el Palacio Público y la famosa Piazza del Duomo antes de disfrutar de un almuerzo típico de la región.Luego, nos dirigiremos a San Gimignano, un pueblo amurallado con 15 torres medievales, conocido como “la Manhattan de la Edad Media”. Tendrás tiempo libre para admirar sus torres y relajarte en este entorno histórico.Terminaremos nuestra excursión en la región del Chianti, donde degustaremos el famoso vino tinto de Chianti y probaremos productos locales, todo mientras disfrutamos del paisaje bucólico. ¡Reserva tu lugar y vive un día inolvidable descubriendo los tesoros de esta maravillosa región!
PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience
Spend a day visiting Volterra with its splendid Roman Theater and the "Beautiful Towers" of San Gimignano. A trip from the Etruscan period to the Renaissance. A wonderful experience among wine, local food, vineyards, olive trees and rows of cypresses in the most genuine Tuscany. Itinerary: • Meet your driver at your location • 1st stop in Volterra, one of the most beautiful viewpoints in Tuscany, visit of the Historic City and the Roman Theatre. • For lunch we will move to a Tuscan farm, to understand the secrets of wine production and enjoy a tuscan lunch with 5 wine tastings • After lunch we will drive through the rolling hills of Chianti, among olive groves, cypresses and vineyards to the medieval town of San Gimignano • We will visit the magnificent Towers of the city and discover the legend of the Black Rooster. In the main square you will taste the best ice cream in the world (Gelateria Dondoli) • The return is expected around 17:00 Take a look: "What to Expect"...
Siena Scavenger Hunt and Highlights Self Guided Audio Tour
The Best Way to Discover Siena: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a traditional Ricciarelli almond cookie in a local pastry shop or enjoy the medieval atmosphere of the Piazza del Campo and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups.The "Complete City" Package Everything you need in one app:Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way.Cultural Context: Read the history and legends of each site as you explore.Insider Tips: Access hand-picked local restaurant and shop recommendations.What you will visit: Pinacoteca Nazionale, Baptistery of St John, Palazzo Piccolomini, Loggia del Papa, Tower of Mangia, Pubblico Palace, Fonte Gaia, Santa Maria della Scala, Facciatone, and the Duomo di Siena.
Florence: Follow the Footsteps of the Iconic Michelangelo's David
Discover the story of Michelangelo's David guided by this engaging in-app audio tour!This tour takes you on a journey around the center of Florence through the story of its greatest treasure – David of Michelangelo! Our adventure begins in a beautiful square with a medieval church, Piazza Trinita. This spot takes you to the origins of David as a Biblical hero.When you reach the stunning Piazza del Duomo, you'll discover the story of the Opera del Duomo Museum and learn how the young Michelangelo was honored with the mission of carving David out of capricious marble. Standing on Piazza della Signoria, you will have all the time in the world to marvel at the hero guarding the Palazzo Vecchio, and to listen to why this particular artwork is so unique.Our route will then lead us to the Medici Riccardi Palace, which was visited by Michelangelo when he was 16 – and can be visited by you anytime, as a museum. Through Piazza San Marco, you will reach the Galleria dell'Accademia, where the original David of Michelangelo is housed. Our tour ends at the Casa Buonarotti Museum located in the family home acquired by Michelangelo himself. On your way to this last spot, you will listen to the stories about the genius' life and reveal the secrets of his enigmatic personality.Let's begin the adventure if you can't wait to know Michelangelo and David better!
From Florence: Small Group Excursion to Siena, San Gimignano and Monteriggioni
Discover the heart of Tuscany with an exclusive 8-hour tour by comfortable, air-conditioned minivan, in a small group that guarantees personal attention and maximum comfort. You will visit three of the region’s most fascinating destinations: Siena, Monteriggioni, and San Gimignano, while enjoying the rolling hills, vineyards, and medieval villages that make this landscape so unique.The first stop is Siena, an elegant city of art famous for the Palio. You will spend 2 hours here, including a one-hour guided tour that takes you through its highlights, such as Piazza del Campo and the medieval alleys that preserve the city’s timeless charm.The journey continues to Monteriggioni, a charming walled village that feels like stepping back in time. Take a short stroll through its streets and capture stunning photos of this fairy-tale town.Finally, you will reach San Gimignano, known as the “Medieval Manhattan” for its iconic towers dominating the skyline. Here you’ll enjoy one hour of free time to explore at your own pace, sip a glass of Vernaccia, or taste one of Italy’s most awarded gelatos.Throughout the day, take the chance to savor Tuscan specialties such as Panforte and Pici, authentic flavors that enrich the experience and connect you to the region’s traditions.Book now and treat yourself to an unforgettable journey through history, culture, authentic tastes, and breathtaking views.
From Siena: Best of Tuscany Wines & Lunch in Montepulciano
Leave Siena behind and travel through the rolling hills of southern Tuscany on a full-day small-group wine tour through the heart of the Val d’Orcia, a UNESCO World Heritage Site.Your first stop is the historic hill town of Montepulciano, where food and wine come together in an authentic Tuscan experience. Sit down for a traditional lunch made with local products, starting with a selection of typical Tuscan cured meats and cheeses. The meal continues with homemade Pici pasta served with slow-cooked ragù, or Pici with tomato sauce for vegetarian guests.During lunch, enjoy a guided wine tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional dishes.After lunch, continue to Pienza, a Renaissance gem famous for its architecture and panoramic views over the Val d’Orcia. Enjoy free time to explore its picturesque streets, artisan shops, and scenic viewpoints.The final stop is Montalcino, home of the world-famous Brunello di Montalcino. Visit a local winery and enjoy a guided tasting, learning about the traditions and aging process behind one of Italy’s most prestigious wines.End your day with a scenic drive back to Siena through Tuscany’s iconic countryside.
Medioeval Games & Quarter Memorabilia Museum Tour in Siena
In the heart of Tuscany, Siena is a city where history is lived through its neighborhoods, known for their strong identity, traditions and sense of belonging. This guided museum experience offers visitors a unique opportunity to step inside one of these communities "The Contrade Civetta" and understand its role in Siena’s cultural life.The museum is housed within a 13th-century fortified complex, the result of a long restoration process aimed at preserving the collective memory of the neighborhood. Originally opened in 1984, the museum was created by recovering and enhancing previously neglected spaces, transforming them into an area of high historical and architectural value. A major expansion completed in 2017 significantly increased the exhibition areas and introduced a new entrance, improving both accessibility and visitor flow while respecting the medieval structure.The guided visit is the core of the experience. Led by a knowledgeable guide, guests follow a carefully designed route through interconnected rooms, conceived as an ideal journey through time that links past and present. The guide introduces the concept of Siena’s neighborhoods, explaining their origins, social role and deep connection to the city’s most famous tradition, the Palio di Siena.As the tour unfolds, the guide provides clear interpretation of the spaces and objects on display. Historic Palio banners won over the centuries are presented alongside the Masgalani, prestigious awards given for the finest historical procession. Through storytelling, visitors learn why these trophies are so meaningful and how they embody pride, rivalry and continuity.The collection also includes ancient ceremonial costumes, sacred furnishings and liturgical objects, each explained within its historical and symbolic context. Paintings, silverwork and devotional items reveal the artistic craftsmanship and spiritual life that have shaped the community over generations.Beyond the ceremonial aspects, the guided tour highlights elements of everyday life. Architectural details, modest spaces and recovered artifacts offer insight into daily routines from the medieval period through the Renaissance. Ceramics and household objects illustrate how ordinary life coexisted with major public events, reinforcing the idea of the neighborhood as a living social structure.Throughout the visit, guests are encouraged to ask questions and engage with the guide, making the experience accessible even to those unfamiliar with Siena’s traditions. Rather than a passive museum visit, this is an interpretative journey that transforms objects and architecture into a compelling human story.
Private Tour from Florence to Siena, San Gimignano & Pisa
During this private tour in a comfortable minivan, you will explore the breathtaking towns of Siena, San Gimignano, and Pisa.In about 1 hour we will arrive in Siena and you'll meet your guide for a tour of the old town. You will see the famous Piazza del Campo, where the renowned Palio takes place every year. Before leaving you will have some free time to walk around the typical medieval alleys.Our tour will continue towards San Gimignano, where you will have free time to explore the city center on your own. On our way from Siena to San Gimignano we will also make a quick photo stop in Monteriggioni.The last gem of our tour will be Pisa: the city is known for its beautiful monuments. You will take a walk in Piazza dei Miracoli and will be able to admire the 11th-century Cathedral, the Baptistery, and the famous Leaning Tower (no tickets included). Before going back to Florence, you will have free time to take amazing pictures and do some shopping.
Dinner in the Vineyards
Enjoy a magical evening in the Chianti region and live the unforgettable experience of a dinner in the vineyards.A unique experience designed to give you only the best of what the Chianti region has to offer in its various declinations: the history, the landscapes, the wine and culinary traditions and the incomparable atmospheres. Other than enjoying a delicious typical dinner of local products and dishes, you will be surrounded by the splendid and charming landscape made of vineyard rows, which so quaintly characterize the Chianti region. The dishes that you will taste, all made of fresh local products, are the fruit of the hard work and care for the land that local producers have been exercising for centuries. Upon your arrival you will be given a glass for you to carry along the visit of the farm’s wineries and thus enjoy a number of wine tastings on this small-scaled wine route. The dinner location will be set to offer you maximum quality and cosiness, as it will be decorated with candles and torches. Not only the gentle sounds of the earth and the vineyards will accompany your dinner under the stars, but also a harmonious musical background, which will perfectly match the succession of dishes. You will taste pappa al pomodoro or ribollita (both typical recipes from the people’s folklore) and a barbecue of meat and fresh seasonal vegetables of the farm. Let yourself get carried away by the warmth and fragrances of the barbecue and the perfumes of the grapevines, which will complete your dinner experience. The cozy rural setting will make for a nice relaxing dinner in the amazing Chianti area.
Tuscany Wine & Hills from Siena
The adventure begins in the charming medieval village of Monteriggioni, where you'll join the other group and head over to the first canteen. Let the rolling hills of Chianti beckon you as you dive into the region's rich winemaking heritage. Visit a winery where you'll not only sample world-class wines but also learn about the craft of producing extra virgin olive oil—a blend of ancient olive varieties that embodies the essence of Tuscany. In the first cellar, you'll taste three different wines, gaining a deeper appreciation for the unique flavors and textures of each. Complement your tasting with a selection of home-produced olive oil and traditional Tuscan bread. Our knowledgeable guides will enrich your experience with insights into Tuscany's deep-rooted history, art, and rural culture.Continue your journey into the scenic Val d'Orcia, stopping first in Pienza, a town where architectural beauty meets breathtaking landscapes. Wander through lanes with evocative names and enjoy panoramic views that have inspired countless artists and poets. Take some free time to explore the town on your own and savor a leisurely lunch.Your tour then takes you to Montepulciano, where the grandeur of Renaissance architecture and the elegance of historic churches will enchant you. Delight in the traditional Nobile di Montepulciano wine as you explore the city and capture its stunning views.The adventure continues with a visit to a second winery, where you’ll taste more locally produced wines, including the renowned Nobile di Montepulciano, paired with traditional snacks. Finally, relax and enjoy the scenic drive back to Siena, bringing your Tuscan journey to a close.
PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence
• EXPERIENCE FOR YOUR PRIVATE GROUP •Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems of Siena and San Gimignano.Visit iconic sites such as Piazza del Campo in Siena, famous for the Palio horse race, stroll among the medieval towers of San Gimignano (UNESCO site), and soak in the authentic atmosphere of the Tuscan countryside.Upgrade your experience with an optional traditional Full Lunch at a local organic farm or winery, for a truly authentic taste of Tuscany.8/9-hr Full-Day private tour of TuscanyPrivate tour for a maximum of 6 travelers (your party only)Visit the medieval cities of Monteriggioni, San Gimignano and SienaHear live commentary of the winery by your driver/guideTaste Craft Chianti Classico wine at a local vineyard (option)Hotel or private address pick-up & drop-offPerfect for couples, families, and small groups looking for a relaxed, authentic, and fully private Tuscany experience.
Private Day-Trip to Siena and San Gimignano
Get personalized attention as you explore Siena and San Gimignano on this 6-hour private day trip from Florence. Skip the hassle of renting a car, as this tour provides round-trip transportation to both locations. Hotel pickup and drop-off included.
San Gimignano, Chianti, and Montalcino Day Trip from Siena
The first part of our day will be dedicated to the territory of Siena and starts with a visit to San Gimignano, the city of a hundred towers and it is also a UNESCO World Natural and Cultural Heritage site. Our tour escort will give you all of the necessary information for enjoying your free time in the town’s historical center, where you will find local artisan shops and millenarian palazzos. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively here, famous for its high quality and also for being the first Italian DOCG wine. After a brief visit, we will relax at a Chianti winery for an optional typical lunch of salami, cheeses, and other local products, accompanied by a tasting of Chianti wines. Our day continues with a trip to Val d’Orcia, another jewel in the Tuscan territory and a UNESCO World Heritage site since 2004. We will travel to Montalcino, which from its hill dominates the 1500 hectares of Brunello vineyards that have contributed to making the area world-famous. Our last stop will be in a local wine cellar where we will taste the renowned Brunello of Montalcino, which finds its place among the first Italian DOCG wines. We will visit the wine cellar and also taste typical local products.
Siena: Small group Cooking Class in Chianti Farmhouse
The Traditions of Tuscany are strongly linked to its flavors and cuisine. We offer our guests cooking classes in the typical Tuscan style, to help them discover our roots and culture in a funny and original way. Discover our cooking class location, right in the heart of the stunning Chianti area. Here you will finally meet with a local chef, and thanks to him learn about the secrets of our cooking, the basic ingredients of our tradition, and the magical way in which we combine them. From bruschetta to homemade Italian pasta to the myriad of crostini, you will bring home a bit of “Tuscanness” to your dinner table. Learn to make this delicious food and then take home what you learned and show it off to your friends and family. Fall in love with Tuscany through its food.
Siena or Sovicille to Florence Airport (FLR) - Departure Private Transfer
Book your Departure Private Transfer from Siena or Sovicille to Florence Airport (FLR) to any hotel or address.Don't go through all the hassle of waiting in a long taxi or shared shuttle queues and use our private, door to door airport transfer.We will contact you immediately after your booking to confirm it and will request any missed details of your trip if any.One day before the trip, you will receive the phone number of your driver for your convenience.Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.• Meeting with a Nameplate• No Hidden Charges• Door-to-door Service
Chianti and Castle Tour from Siena
Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Visit the Castellina in Chianti before enjoying wine tasting at a winery in the Chianti area.The beautiful ruby-red color and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine results from the wise blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes.On this trip, discover the breathtaking, uncontaminated landscapes that have been cradling the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in the hills of this region.The sounds, scents, and flavors of this land will capture your senses through a unique experience. Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time.Later, move on to a winery in the middle of the Chianti Classico area, where you’ll have a wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.
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