Siena Architecture

Our most recommended Siena Architecture

From Florence: Tuscany Day Trip with Optional Lunch and Wine

1. From Florence: Tuscany Day Trip with Optional Lunch and Wine

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

Siena: Siena Cathedral Complex Pass (OPA SI Pass)

2. Siena: Siena Cathedral Complex Pass (OPA SI Pass)

See notable features of the Duomo of Siena with the OPA SI fast-track entry pass. In addition to discovering the Cathedral of Siena, visit the Baptistery, the Crypt, the Piccolomini Library, and the adjacent Museo dell'Opera, Oratory, and Facciatone viewpoint with one convenient ticket. Enter the Duomo and be amazed by its grand scale as you stroll along its stunning mosaic marble floor. Admire sculptures such as The Feast of Herod by Donatello and St. Paul by Michaelangelo, amongst many artworks which are dotted around the cathedral. Visit the Baptistery of San Giovanni within the Duomo to marvel at the splendid Baptismal Font. From here, head down into the Crypt, the underground quarters that remained hidden for more than seven centuries. Then, stroll through the Piccolomini Library and gaze up at the vibrant and colorful frescoes which adorn its walls. Admire the stunning work by Pinturicchio, which depicts ten episodes from the life of Pope Pius II. Access the Museo dell'Opera which houses a selection of archaeological fragments and artwork once part of the cathedral. See a variety of Gothic sculptures by Giovanni Pisano and paintings by Ambrogio and Pietro Lorenzetti. Head into the Oratory of San Bernardino to admire the collection of the Diocesan Museum of Religious Art, with its core at the upper oratory chapel. Discover a variety of Siennese paintings from between the 13th to the 18th century. Finish up your visit to the complex with a climb up to the Facciatone viewpoint. Be enchanted by the unforgettable view over the city of Siena and the beautiful rolling hills of the Tuscan countryside.                                                                                                                                        

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

3. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

Discover UNESCO World Heritage Sites and taste Chianti wines on a full-day trip from Florence. Visit Pisa, San Gimignano, and Siena, and savor a traditional Tuscan lunch.  First, head to Pisa to marvel at the Piazza dei Miracoli, Pisa Baptistery, Pisa Cathedral, and, of course, the famous Leaning Tower of Pisa. Continue to a wine villa in the Chianti countryside. Enjoy a tour of the estate and learn about its history in the medieval chapel before your first tasting of Chianti Classico on the panoramic terrace. Next, relish a typical lunch accompanied by two of the estate's products, a "Riserva" and an IGP wine. After lunch, relax a while in the villa's luscious gardens before going to the medieval town of San Gimignano.  Then, follow the scenic roads to Siena for a tour of the city's monuments and piazzas. Visit Piazza del Campo — the site of the Palio di Siena horse race — and admire the cathedral's exterior in Piazza del Duomo. After some free time, return to Florence.

Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

4. Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

Benefit from fast-track entry to Siena Cathedral and admire the stunning artwork and architecture of its interior. Walk along its ornate marble mosaic floor and visit the Piccolomini Library known for its collection of vibrant frescoes. Skip the line and enter the Cathedral and admire one of the foremost masterpieces of renaissance art and architecture in Italy. Gaze at elaborate altarpieces, a sculpture by Michelangelo, and all manner of ornate decorations scattered throughout its vast interior. Enter the Piccolomini Library, which contains a sprawling series of 10 frescoes by Pinturicchio chronicling the life of Pope Pius II. Gaze upwards at the domed ceiling, masterfully adorned with complex patterns and further scenes from the pope’s life.

Siena: Guided City Tour with Cathedral Skip-the-Line Entry

5. Siena: Guided City Tour with Cathedral Skip-the-Line Entry

Explore the beauty of Siena on a small group or private walking tour. See its famous monuments and hidden treasures with an expert guide. Benefit from skip-the-line entry tickets to Siena Cathedral. Meet your guide at the San Domenico Basilica and admire its Gothic architecture. Follow a winding route to take in panoramic views of the city, including the Duomo and Torre del Mangia. Find out about Siena in the Middle Ages, see the imposing palaces said to be the oldest in the area. Have a break to take in the charm of the 14th-century seashell-shaped square, Piazza del Compo, a UNESCO World Heritage site. Admire the magnificent Fonte Gaia fountain with its side reliefs of "The Creation of Adam" and "The Flight from the Garden of Eden." Learn about the history of the contrada (districts) that challenge each other twice a year during Siena’s Palio horse race. Walk to one of the most typical contrada and immerse yourself in the authentic atmosphere. Follow your guide to see one of the local pastry shops that reflect the glory of Italy in using the centuries-old recipes to make traditional Ricciarelli and Panforte. Finally, explore one of the most fascinating cathedrals in Italy with pre-reserved tickets. Follow your guide to marvel at the magnificent marble mosaic inlay floor, stained glass, and medieval masterpieces by Duccio and Pisano. See the Renaissance highlights: several Donatello, Michelangelo, and Bernini sculptures and frescoes by Pinturicchio in the Libreria Piccolomini. Armed with a wealth of knowledge about Siena, say goodbye to your guide in the square in front of the cathedral.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

6. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside, followed by a stop in Siena. Here, a specialist guide will lead you on a walk through the city's historical center. Skip the ticket line to see the interior of the magnificent cathedral, and pass through the shell-shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

Siena: Palazzo Pubblico Entry Ticket

7. Siena: Palazzo Pubblico Entry Ticket

Enter the Palazzo Pubblico of Siena and visit the Civic Museum with this entry ticket. Located inside the Palazzo Pubblico, the Civic Museum is a 13th-century building home to impressive wall-to-wall fresco paintings. Explore the museum to learn about the history of Siena and see precious artifacts. Exchange your voucher for an entry ticket at the ticket office and begin your visit in the Sala del Risorgimento. This room hosts fresco paintings that depict the life of Vittorio Emanuele II, the first king of Italy. Walkthrough the Sala di Balìa and see wall paintings from the 15th-century by Spinello Aretino and Martino di Bartolomeo. Also, see the Sala dei Cardinali where precious carved coffers keep reliquaries. Move forward to the Sala del Concistoro, famous for its Beccafumi vault, and see Taddeo di Bartolo's 15th-century Cappella. Continue on to the Sala del Mappamondo, the widest room of the Palazzo Pubblico and used as the meeting place of the General Council. See the famous Maestà, a Gothic masterpiece painted by Simone Martini. The museum entry ticket also includes a visit to the 14th-century gallery, Loggia dei Nove, which offers a beautiful view of the landscape behind Palazzo Pubblico.

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

8. Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

9. Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Along the way that will lead you to Siena, stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries. It is renowned for its tall towers, wonderful frescoes and many other valuable works of art.  Here, be led to the heart of the historical center, where you will have free time to explore. Following San Gimignano, stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day.  Enjoy some free time to visit this village. Then, crossing the gently rolling Chianti hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies. Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo.  Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race.  The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public.  If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

Brunello di Montalcino Full-Day Wine Tour with Tastings

10. Brunello di Montalcino Full-Day Wine Tour with Tastings

Wine lovers will enjoy this full-day tour through the beautiful Tuscan landscape with stops to visit some typical local wineries. Explore the famous wine hills of Montalcino and learn about the process and passion involved in creating Brunello di Montalcino, one of Italy's most prestigious wines. Your tour begins with a drive along the ancient Roman road from Siena to the famous wine hills of Montalcino. The first stop will be at a small, typical area winery where you’ll have a chance to walk in the vineyards, explore the cellars, and enjoy an introductory tasting of world-famous Brunello wine. Next, you’ll head to Montalcino, the hill town that gives its name to the region and its wines. Here you’ll have the opportunity to climb the fortress walls, spend some time browsing the shops and tasting the Brunello wines in wine bars, or simply enjoy the incredible views of the valleys and vineyards below. After visiting the town of Montalcino the tour continues on to the stunning ancient mystical Benedictine Abbey of Sant Antimo, a special place in a tranquil setting. You’ll enjoy a traditional Tuscan lunch at a family-run winery, accompanied by the delicious wines produced at the facility. Afterwards, you’ll have the opportunity to visit the farm. In the afternoon you’ll visit a third winery where you’ll get a detailed description of the wine-making process, and learn how the vines are cared for and about the long aging process in oak barrels. After visiting the cellars and getting to know the winemakers, you’ll sit down for a final tasting of this nectar of the gods.

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Frequently asked questions about Siena

What top attractions are a must-see in Siena?

What are the best day trips and excursions from Siena?

The best day trips and excursions from Siena are:

San Gimignano

Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.4 / 5

based on 4,566 reviews

The first winery was no i out t so good. Even if it is small then the place could be cleaner and neater. The second one Casa Emma is wonderful. Scenery is what we wanted to see and it’s there. The wines are good and cold cuts satisfying. The crown of the tour is the third one Poggio Torselli. The gardens is beautiful and small castle is restored wonderfully.

Idiana was terrific, charming, knowledgeable and answered our many questions with a smile, she made the tour fun and interesting. She had a very easy way about her and easily transitioned to highlight key places and history of Siena pointing out specific things to really heighten out tour

It was an amazing tour! Both our guide Sara and driver Nikolai were excellent. The whole trip took 12-13hrs but it was totally worth it. Siena was our favorite. Walkabout Tours were really professional and organized. We had delicious pasta and wines for lunch. Highly recommend this tour.

Excellent choices of attractions and lunch. Be prepared for alot of walking and a long day....12hours+

This was a great tour and it was a great way to see Siena!