Day Trips From

Day Trips From
Day trips from Siena

Tips and Advise for day trips from Siena by Road to Travel Inc.

Monday, October 12, 2015

The charming village of Montefioralle 

If we had to pick the prettiest hamlet in Chianti it probably would be Montefioralle. Enclosed within its original walls, this tiny village is certainly one of the best-preserved mediaeval fortified villages in the area and in the whole of Tuscany. It sits on a hilltop just above Greve in Chianti, it is a great destination for a relaxing day trip from Siena or Florence

Montefioralle - Panorama
Wondering along narrow cobbled streets you will see characteristic tower houses and two sets of ancient walls, reminders of the days when the village was a stronghold at the forefront of the long bloody feud between Florence and Siena. During the Renaissance, rich silk merchants the Vespucci built a lavish country house on the main street, which has survived and can be recognized by a carved letter “V” and wasp above the doorway. Historians believe that the future explorer Amerigo Vespucci was born here.

At the top of the hill stands the Church of S. Stefano where you can admire beautiful frescoes dating back to the 13th century. Just outside Montefioralle is another example of rural Romanesque style in Tuscany, Pieve di San Cresci built in the 12th century. 

Montefioralle - Street
If you visit the village in March, you can enjoy the annual Festa di Frittelle during which locals cook sweet rice fritters in a giant pot in the central square that are eaten accompanied by dessert wine Vinsanto. In May Montefioralle hosts the Wine of the Castle Festival during which visitors can taste excellent Chianti from local producers.

Make sure to stop at the small family-run restaurant “Taverna Del Guerrino” with a delightful terrace overlooking the nearby green rolling hills. The menu is short and all dishes are made strictly with local ingredients: thick traditional tomato soup “Pappa al Pomodoro”, pasta with a wild boar sauce and juicy grilled steaks of local chianina beef.

Photos via Flickr by: Jon Culver, Dolf van der Haven.

Saturday, September 19, 2015


If you are staying in Siena for a few days try to hop over to Monteriggioni, an enchanting small hilltop town nearby. It is circled by virtually intact medieval walls that remind of the days when Monteriggioni served a strategic lookout point at the Siena’s front-line defence against the bellicose Florentine Republic. 


So important was this fortified town in its glory days that it even earned a mention in Dante Dante’s Divine Comedy:

“As with circling round
Of turrets, Monteriggioni crowns his walls;
E’en thus the shore, encompassing the abyss,
Was turreted with giants, half their length
Uprearing, horrible, whom Jove from heaven
Yet threatens, when his muttering thunder rolls”.

There are a few points where you can climb up the 10-metres high ancient walls to admire the neat vineyards and rolling hills of the Tuscan countryside around Monteriggioni and great views of the old town and the 14 turrets that have changed little since their construction in the 13th century.

Piazza di Roma

On the main square, Piazza di Roma, you will find the pretty Church of Santa Maria Assunta that has been offering housing to pilgrims traveling the Via Francigena route for many centuries. In old days, the fortified village had large vegetable gardens that fed its population during frequent sieges, which today have been tuned into pretty gardens. 

Monteriggioni is the perfect place to relax and forget about the hustle and bustle of big cities. Strolling around the old centre, admiring old stone buildings and elegant arches is better done without rush. You can taste local Chianti and Brunello in small wine shops and enjoy delicious Tuscan dishes in tiny restaurants.

Church of Santa Maria Assunta

Every July the town celebrates the Medieval Festival of Monteriggioni. The streets fill up with locals dressed up in period costumes who play medieval music, dance, and demonstrate ancient crafts recreating the atmosphere of the castle centuries ago. Restaurants an trattorie offer medieval dinners and visitors have to exchange modern money for Middle Age coins to buy food and wine. 

Photos via Flickr by: Isabelle Puaut, Henrik Berger Jørgensen, Javier G.Valdivia.

Thursday, August 27, 2015

Terre Senesi

A small hamlet of San Giovanni d’Asso is located 19 miles southeast of Siena, in the area known as the Clay Hills

Its rich history can be traced back to the dawn of Christianity when an ancient local Longobard church, San Pietro a Pava, became an important religious center. The hamlet shaped up in the Middle Age when a castle was built here. Over the course of centuries, the hamlet passed from one noble Siennese family to another. Due to its non-strategic position, away from the main commercial routes, San Giovanni d'Asso has never been in the center of any historic events and has remained a sleepy charming village. Just like in the old days locals grow grains, olives and make wine, although, nowadays it is better known for excellent white truffles.

Crete Senesi

Every year in November the hamlet celebrates a two-week Festival of the white truffle (Sagra del tartufo bianco). The streets fill up with stands selling the precious tuber and traditional foods and restaurants serve various dishes made with it. There is also a museum dedicated to tartufo bianco, the first one in Italy, housed in the beautiful 13th century castle overlooking the hamlet that tells about every aspect of the fragrant tuber and takes visitors on a sensorial journey into its fascinating world.
The hamlet’s main 14th century church of San Giovanni Battista has no opulent décor but close to the heart of many Christians as it guards a number of religious relics of Saint Peter, Saint John and Saint Catherine of Siena. Another lovely church that is worth a visit is San Pietro in Villore. First mentioned in documents dating back to the 8th century , it has an atmospheric dimly lit crypt and a an elegant bell gable.

Castello - San Giovanni d'Asso

Despite its minuscule size, the hamlet has a few excellent restaurants where you can indulge in seriously good local food. La Locanda del Castello serves delicious pasta with a white truffle sauce and local Sienese porc chops rolled in almonds. In Osteria delle Crete you can taste mouth-watering salami and cheeses with truffles.

Photos via Flickr by: Carlo Tardani, Antonio Cinotti.

Friday, July 24, 2015

Montepulciano: art, wine and Tuscan sunshine

Less than an hour drive from Siena is Montepulciano, a small town known as a “jewel of the 1500s” because of its Renaissance architecture and art. You can pack a lot in a day trip visiting this car-free town.

No major building work has taken place since 1580 within Montepulciano’s old centre. The spectacular central square, Piazza Grande, is flanked by beautiful buildings of the Duomo, Palazzo Comunale, Palazzo Tarugi and Palazzo Contucci. Climb to the top of the tower of the Palazzo del Comune to see the surrounding Tuscan countryside with its gentle hills, vineyards and olive groves.


Il Duomo, or the Cathedral of Santa Maria Assunta dates back to the 17th century and is adorned by many masterpieces, such as the gold-decorated altarpiece created in 1401. Do not miss the Baroque church of Santa Lucia which has an altarpiece by Luca Signorelli and the beautiful 15th century church of  St. Augustine, which has a wooden crucifix attributed to Donatello.
Follow the main long street, the Corso, to see a spectacular display of power and riches: each palazzo built by a noble family from the past can tell a story of this magnificent town, an ancient enemy of Siena. Downhill, only 10 minutes on foot from the town, you will find the old pilgrimage church of San Biagio, one of the best examples of Renaissance art.

Montepulciano - Palazzo Comunale

Montepulciano is world-famous for its elegant red wine, Vino Nobile di Montepulciano, and its strong wine-making traditions, which can be traced back to the 8th century. During Renaissance the town was renowned for its wine described as "un vino da signori" (a wine for aristocrats). There are many cellars in town where you can enjoy Vino Nobile: Enoteca La Bottega del Nobile (Via di Gracciano nel corso, 95), Antico Caffè Poliziano (Via Voltaia nel corso, 27), with its beautiful terrace boasting stunning views over the Valdichiana, and Cantina de' Ricci, one of the oldest wine cellars in the world.

Photos via Flickr by: James Good, Andy Hay.