Small-Group Montepulciano and Pienza Day Trip from Siena

Siena , Italy

Small-Group Montepulciano and Pienza Day Trip from Siena

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About this experience

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm!

Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.

Available options

Small-Group Montepulciano and Pienza Day Trip from Siena

What's included

Transport by air-conditioned minivan (maximum 8 passengers)

Alcoholic Beverages

Lunch on local farm with wine

Driver/Guide

Detailed itinerary

Stop 1 Pass by

Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.
Travel south out of town on one of the most panoramic roads of Tuscany, through the characteristic moonscapes of the Crete Senesi.

Enjoy brief stops along the Crete Senesi for for photo opportunities before visiting a quaint, non touristic medieval hamlet. Continue along this stunning landscape and reach the UNESCO heritage site of the Val d’Orcia, where you come across some of Tuscany’s most iconic postcard pictures.

Stop 3

Arrive to the beautiful, utopian renaissance town of Pienza, one of the first towns to be entirely planned out on paper by important architects of the time. These were called upon by Pope Pius II, the humanist pope who wanted to renovate his native town and bring it new splendor.

Spend your leisure time exploring the Romanesque church of Corsignano or the ideal, Renaissance Cathedral and walk along the scenic route overlooking the valleys and hills beyond. Browse the pretty streets of this gem of a town or some of its many shops of local crafts and products.

Stop 5

Visit a val d'Orcia dairy farm for a wholesome and refreshing lunch based mainly on the fresh ingredients produced on the farm. Here you can learn about the pecorino sheep cheese making processes, visit the farm animals and learn about the lifestyle of the area. Weather permitting, lunch will be served on a panoramic terrace, overlooking the valley below.

In the afternoon, visit one of the biggest and proudest of the Tuscan hill towns, Montepulciano. This town was first under the dominance of medieval Siena and then became an ally to renaissance Florence: here you can recognize the influences of both Republics in its architecture and art. Located on a steep hill, you can look over the ledge at the the Tuscany - Umbrian border.

Visit the main square, Piazza Grande, and explore one of the many old wineries carved out of the ground below the city, and taste the Vino Nobile that was produced by the many important and noble families that one lived here.After a short walk around town with your guide, enjoy some free time on a second tasting of the Nobile wine or visit the town’s many stores, palaces, churches and streets. As you follow the main road down the hill, imagine how hard the “Bravio delle Botti” town festival must be: a competition between the neighborhoods of the town that race wine barrels from the bottom of the hill, all the way to the top.
On some occasions the itinerary might vary a little. In this case, the tour could be slightly modified but will maintain a similar general imprint, of the same duration and with all the same inclusions.

What's not included

Hotel pickup and drop-off

Gratuities

Available languages

Guide guide

Reviews breakdown

Viator 4.9

168 reviews

5★

151

4★

3★

2★

1★

Tripadvisor 4.9

112 reviews

5★

110

4★

3★

2★

1★

Important information

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Specialized infant seats are available

Not recommended for travelers with poor cardiovascular health

Suitable for all physical fitness levels

Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol

Meeting point

Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.

About Siena

Siena is a medieval city in Tuscany, Italy, renowned for its rich history, stunning architecture, and the famous Palio horse race. The city's well-preserved historic center is a UNESCO World Heritage site, offering a glimpse into Italy's medieval past with its cobblestone streets, towering churches, and grand piazzas.

Top Attractions

Piazza del Campo

Piazza del Campo is the heart of Siena and the site of the famous Palio horse race. This stunning, shell-shaped square is surrounded by historic buildings and is a must-visit for its architectural beauty and vibrant atmosphere.

Historical 1-2 hours Free

Siena Cathedral (Duomo di Siena)

The Siena Cathedral is a masterpiece of Italian Gothic architecture, featuring stunning marble facades, intricate mosaics, and beautiful frescoes. The cathedral's interior is equally impressive, with a richly decorated nave and a magnificent marble floor.

Religious 1-2 hours €8-12

Basilica of San Domenico

The Basilica of San Domenico is one of the largest churches in Siena and houses the relics of St. Catherine of Siena. The church's interior is adorned with beautiful frescoes, sculptures, and a magnificent choir.

Religious 1 hour Free (donations appreciated)

Palazzo Pubblico

The Palazzo Pubblico is a historic palace that houses the Museo Civico, which showcases a collection of medieval and Renaissance art. The palace's courtyard and tower offer panoramic views of the city and surrounding countryside.

Historical 1-2 hours €9-12

Santa Maria della Scala

Santa Maria della Scala is a historic hospital and museum complex that showcases the city's rich history and art. The complex features beautiful frescoes, sculptures, and a labyrinthine network of underground passages.

Historical 1-2 hours €7-10

Must-Try Local Dishes

Pici all'Aglione

A traditional Tuscan pasta dish made with hand-rolled pici pasta and a garlic and tomato sauce.

Main course Vegetarian

Ribollita

A hearty bread and vegetable soup, often made with cannellini beans, kale, and carrots.

Soup Vegetarian

Panforte

A traditional Siena dessert made with dried fruits, nuts, and spices, often enjoyed during the Christmas season.

Dessert Vegetarian, contains nuts

Peposo

A traditional Tuscan beef stew, slow-cooked with wine, garlic, and spices.

Main course Contains meat

Popular Activities

Hiking in the Tuscan countryside Cycling tours Wine tasting tours Visiting hot springs Enjoying local cuisine Exploring historic sites Visiting museums Attending the Palio horse race

Best Time to Visit

June to August, July 2 (Palio di Provenzano), August 16 (Palio di Assunta)

The peak season in Siena is during the summer months, especially around the Palio horse races. The weather is warm and sunny, perfect for exploring the city's outdoor attractions and enjoying the vibrant atmosphere.

22°C to 34°C 72°F to 93°F

Practical Information

Language

Official: Italian
Widely spoken: English, French, Spanish
English: Moderately spoken

Currency

Euro (EUR)

Time Zone

GMT+1 (CET), GMT+2 (CEST) during daylight saving time

Electricity

230VV, 50HzHz

Safety Information

Overall Safety Rating: Generally safe

Siena is generally safe for tourists, with low crime rates. However, pickpocketing and petty theft can occur in crowded areas, so it's important to stay vigilant.

Important Precautions:

• Keep valuables secure
• Be cautious of pickpockets in crowded areas
• Use licensed taxis or ride-sharing apps

Getting there

By air

Florence Airport • 80 km (50 miles)
Pisa International Airport • 120 km (75 miles)

By train

Siena Station

By bus

Siena Piazza Gramsci, Siena Piazza del Duomo

Getting around

Public transport

The bus system in Siena is efficient and covers most parts of the city and nearby towns. Buses are a convenient way to get around, especially for those staying outside the city center.

Taxis

Available • Apps: MyTaxi, FreeNow

Rentals

Car, Bike, Scooter

Neighborhoods

San Martino San Domenico Santa Maria della Scala

Day trips

Chianti Wine Region

20-40 km (12-25 miles) • Half day to full day

The Chianti region is famous for its vineyards, rolling hills, and picturesque villages. It's a perfect day trip for wine enthusiasts and those looking to explore the Tuscan countryside.

San Gimignano

35 km (22 miles) • Half day to full day

San Gimignano is a medieval hilltop town known for its towering houses and stunning views of the Tuscan countryside. It's a UNESCO World Heritage site and a must-visit for history buffs.

Val d'Orcia

60-80 km (37-50 miles) • Full day

Val d'Orcia is a UNESCO World Heritage site known for its stunning landscapes, hot springs, and picturesque villages. It's a perfect day trip for nature lovers and those looking to relax in a beautiful setting.

Festivals

Palio di Siena • July 2 and August 16 Siena Jazz Master Classes • July Siena International Film Festival • November

Pro tips

Visit the historic sites early in the morning or late in the afternoon to avoid crowds
Try local specialties like pici pasta, ribollita, and panforte
Explore the city's hidden gems, such as underground passages and historic streets
Attend the Palio horse race for a unique cultural experience
Take a day trip to the Chianti wine region for wine tasting and scenic landscapes