Day Trips from Siena to Pienza

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Our most recommended Siena Day Trips From

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.

From Florence: Chianti Hills Wineries Tour with Tasting

2. From Florence: Chianti Hills Wineries Tour with Tasting

Immerse yourself in Italy's renowned winemaking culture on this guided tour by van from Florence. Leave the city behind as you head out into the Tuscan countryside, marveling at the landscape around you. Visit two local wineries and enjoy wine tastings in both of them, learning about the wine-making process from locals. Arrive in the charming town of Radda in Chianti and visit one of the town’s traditional wineries. Enjoy a tasting session of 3 regional wines, then have the opportunity to purchase them. Spend some free time exploring the narrow streets of the town. Continue towards a traditional farm and winery. Learn about the winemaking process from grape to glass. Then enjoy another tasting session of 3 Chianti wines as well as local products. Finally, sit back and relax on the return journey to Florence.

S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & Tasting

3. S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & Tasting

First arrive in San Gimignano, a tiny medieval town that has remained intact through the centuries. Sitting upon a hilltop, it is famous for its numerous towers, frescoes, and other art treasures. Enjoy more free time to discover this fascinating city on your own. Next, stop at the charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous walls, which remained standing to this day. Enjoy some free time to visit this place. Afterwards, you will cross the gently Chianti rolling hills, arrive at a small and typical winery. Taste 4 fantastic wines, then sample balsamic vinegar and other locally produced zero food miles products, to end this memorable experience in the heart of Tuscany. Your final stop is in Siena, where you will have free time to walk along the narrow medieval streets admiring the splendid palaces, the Cathedral, Libreria Piccolomini, and the famous shell-shaped Piazza del Campo.

From Siena: Vespa & Chianti Tour in the Tuscan Hills

4. From Siena: Vespa & Chianti Tour in the Tuscan Hills

Have fun riding a Vespa along the scenic and peaceful roads on the Tuscan hills. An alternative way to admire the sights of Chianti, wrapped in the sight of the Tuscan countryside and the sound of the working farms. You can join the tour driving an original Vespa Scooter or you can choose to be driven by an expert driver. You will do this experience with an expert tour leader who will be showing you around a small medieval villages situated in the heart of Tuscany. Those who do not feel confident enough about riding on their own can opt to ride with one of the expert escorts. This tour takes one day, during which you will see the most of the Chianti hills. Before come back to Siena, you will stop in a renowned farm for a wine tasting paired with a delicious light lunch.

From Siena: Brunello di Montalcino Wine Tour by Minivan

5. From Siena: Brunello di Montalcino Wine Tour by Minivan

Brunello, considered the best wine in the world, has its ancestral roots in the passion of the inhabitants of Montalcino and in the ancient winemaking tradition, handed down from one generation to the next. The town of Montalcino, with its Sangiovese grapes the wine is produced from, stands on a charming hill that lets you relish its natural wholesomeness. The town, its ancient fortress, and some of the best wineries in the world are the focus of this specialized tour. The winemaking process which includes a long maturation in casks made from valuable wood, make Brunello the “Italian ambassador in the world of our winemaking reality.” Taste prestigious wines from some of the finest wineries in Montalcino and enjoy the wonderful surrounding area.

From Siena: Pienza and Montepulciano Small-Group Tour

6. From Siena: Pienza and Montepulciano Small-Group Tour

Travel along one of the most panoramic roads in Tuscany, driving the characteristic moonscape of the Crete Senesi en route to the medieval hamlet of Pienza in the Val D’Orcia valley. One of the first towns to be entirely planned on paper by important architects and artists of the time, Pienza was commissioned by Pope Pius II - the humanist pope - to help him renovate his native town and bring it to new splendor. A wholesome lunch, based on fresh local ingredients will be waiting on a beautiful terrace (weather permitting) at a local dairy farm. Learn about the process of making Italy’s famous pecorino cheese. Continue in the afternoon to Montepulciano, one of Tuscany’s largest hill towns. Under the dominance of Siena in the Middle Ages, and Florence during the Renaissance, today it is renowned for its wine. See influences from both towns in the architecture and art of the historic center, located on a steep hill with beautiful views of the Tuscan and Umbrian border. Go to the main Piazza Grande, and tour one of the many wineries, carved out of the earth below the city. Discover some of the palaces of the noble families that once lived here. After a short walk around town with a guide, enjoy some free time to taste the fabled wines, or continue to explore the palaces, churches and streets on your own. As you follow the route of the main road downhill, imagine how hard the “Bravio delle Botti” festival must be; a competition to race wine barrels from the bottom to the top of the hill!

From Siena: San Gimignano, Montalcino & Wine Tasting

7. From Siena: San Gimignano, Montalcino & Wine Tasting

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers, a UNESCO World Natural and Cultural Heritage Site. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation. The final stop of the day will be a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines. Sample other typical local products as well.

Brunello di Montalcino Full-Day Wine Tour with Tastings

8. 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.

From Siena: Val D'Orcia Wine Tour

9. From Siena: Val D'Orcia Wine Tour

Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. Go to the picturesque town of Pienza, and taste world-famous wines produced in Montalcino and Montepulciano. Meet your guide in Siena and join the rest of the group to start your full-day tour. Depart Siena and transfer to a wine cellar in Montalcino. Cross gently rolling hills full of vineyards, and then sample local wines served with a delicious snack of the local produce. Continue to Pienza to discover the “Touchstone of Renaissance Urbanism.” Considered an artistic jewel of the landscape of Val d’Orcia, Pienza is a perfect combination of architectural beauty and harmony. Most of the lanes bearing impressive names overlook the breathtaking landscape of the Val d’Orcia. Unique smells and flavors are entwined with this natural and artistic heritage. Pienza’s most renowned tradition is pecorino cheese. End the tour at Montepulciano, where the stateliness of its Renaissance buildings and the refined beauty of the town's churches mix with the ancient tradition of wine making. Enjoy some free time before your return transfer to Siena by bus.

From Siena: Chianti and Castles Tour with Wine Tastings

10. From Siena: Chianti and Castles Tour with Wine Tastings

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Explore the gardens of the Brolio Castle and visit the Castellina in Chianti before enjoying wine and local product tastings at 2 wineries 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. The tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and join a guided walk of the castle gardens. When the tour of the garden ends, join a wine tasting paired with typical Tuscan food. Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

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What people are saying about Siena

Overall rating

4.5 / 5

based on 5,046 reviews

I highly recommend the tour for people, which want to see some highlights of Toscany. As I’m not eating mean I was even surprised to have some nice pasta and other dishes which made my stomach happy and Alexandro, he was a guide with a passion, always there when you have some questions

Our guide Ale from Walkabout Florence was amazing! Spent the time to talk to each of us, and was more than happy to answer questions and give us suggestions about the places we went to!

Our guide Sonia was wonderful! If we were to do anther excursion like this, we’d do only 2 towns, 3 seemed too rushed.

It was great, the landscapes, the lunch, the cities visited, everything was very beautiful.

Tour guide was fun and gave us tips for good wine and gelato places to go to! :)