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7 day travel guide in Tuscany: Siena, San Gimignano and Wine | WishCasting

(This travel guide works best with a car and with a 1 week holiday)

Straight to the travel guide:

What, where and how is Tuscany?

Located at the heart of Italy, Tuscany's one of its 20 regions sharing borders with Umbria, Lazio, Liguria, Emilia Romagna and Le Marche.

Main cities are:

Toscana Italy
Tuscany's Region

What's so special about Tuscany?

Rustic farms, manicured fields, cypress driveways and roman-medieval-renaissance citadels overlooking vast green landscapes from hill tops. Tuscany's the best example of a romantic fairy tale, only to be pictured with wine, excellent food and a slow paced lifestyle.

Being for centuries at the center of Italian history explains why this beautiful region has so many Unesco world heritage sights and iron-strong traditions.

When to visit Tuscany?

Best time of the year is June, July and August. It can get really hot but if you can bare the heat we recommend that period. Medieval festivals happen in this period:

  • Siena: you have the Palio horse race on 2nd of July and 16th of August

  • Firenze: Calcio Storico where the final match is played on June 24th

  • Monteriggioni: first half of July

  • San Gimignano: Medioevo in Rocca

Plenty other festivals are scattered around other regions and towns. Discover them on your own by roaming around.

Summer has the longest days, getting around with shorts and t-shirt is super comfortable and gives you the best holiday experience possible.

Our itinerary:

  1. San Gimignano

  2. Agriturismo dell'Arnano (Agriturismo is a luxurious farm stay away from the city)

  3. Siena and it's Palio horse race

  4. Monteriggioni

  5. La Speranza Restaurant

  6. Castles around our farm stay

  7. Castellina in Chianti

  8. Cecchi Winery

1)San Gimignano

San Gimignano
San Gimignano and its fine tower skyline


San Gimignano is a small medieval hill town in the province of Siena. Known as the Town of Fine Towers, it's famous for its medieval architecture, preserved tall tower houses and encircling walls located on the top of a hill (324 m above sea level).

Within the walls, the well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. The Palazzo Comunale, the Collegiate Church and Church of Sant' Agostino contain frescos.

The "Historic Centre of San Gimignano" is a UNESCO World Heritage Site. The town is also known for it's saffron, the Golden Ham, and its white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grape which is grown on the sandstone hillsides of the area.

We recommend visiting:

  • Torre Grossa

Torre Grossa Palazzo Comunale
Torre Grossa, part of the Palazzo Comunale (Town Hall)

  • Sotto le mura (below the fortified walls there's a walking path that follows the perimeters of the town, this part is the most intriguing since it's silent, natural and few tourists know about it) ---> check the video to see them

  • The two main churches: The cathedral Collegiata and the church Sant'Agostino (check the frescoes)

We recommend eating at:

  • La Mandragola

La Mandragola ristorante San Gimignano
La Mandragola, 100 meters from the main square

Typical dishes are:

  • Pici cacio e pepe

  • Ribollita

  • Tagliatelle al Tartufo (non uniform pasta with fresh Truffle grated on top) MUST TRY

  • Bistecca Fiorentina (Fiorentina Steak)

  • Fagioli con salsiccia

Traditional Wine is Vernaccia di San Gimignano

Gallery :

2)Agriturismo dell'Arnano - Farm stay

We chose to book a Farm stay (Agriturismo in Italian) away from the city noise and stress.

We chose Agriturismo dell'Arnano in Sovicille, 15 km from Siena and very close to other places we wanted to visit during our stay.

This agriturismo cost us 324 euros for 3 guests for 7 nights for a total of 15.5 Euros pp per night. That's insane! The place is gorgeous and luxurious, catered with a kitchen, swimming pool and all the commodities you'd want at home.

The owner brought us their home made Chianti Wine, Vin Santo liquor, Cantucci and olive oil. We met her dog and paid a visit to their barn. They have sheep, goats, wild boars, pigs, chickens, peacocks.

We swam, had Italian aperitivo, did yoga in the garden.

We loved it and we definitely recommend it.

I would never recommend a hotel in Tuscany. That would be so wrong and unnecessarily expensive.


(we use it all the time)

  • Create a list of places you want to visit and mark them down on saving them as your favorites

  • Understand which location on the map would be strategically close to all the places on the list created on step 1.

  • Go to and enter that location/town in, the length of your stay and amount of people

  • Sort by price

  • Scroll down until you find one with good reviews. Right click and open in new tab. Do this several times.

  • Check the tabs you've opened for pictures and reviews, if they convince you keep them. Whatever doesn't convince you close it.

  • Once you're left with 3 or so candidates, you can start discarding the ones with less reviews, lower rating, higher price, worst pictures or further distance from the city.

By now, if you followed the above method, you should have the best budget offer Guaranteed!

3)Siena and the Palio Horse Race
Piazza del Campo Siena
Siena's Piazza del Campo


Siena is a city in Tuscany, Italy.

The historic centre of Siena has been declared by UNESCO a World Heritage Site.

It is one of the nation's most visited tourist attractions, with over 163,000 international arrivals in 2008. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year.

Population (30 November 2012)  Total 52,774

History and Origins:

According to local legend, Siena was founded by Senius and Aschius, two sons of Remus and thus nephews of Romulus, after whom Rome was named.

wolf romulus remus
she-wolf with suckling infants, symbol of Siena

Supposedly after their father's murder by Romulus, they fled Rome, taking with them the statue of the she-wolf suckling the infants (Capitoline Wolf), thus appropriating that symbol for the town.

Siena's Coat of Arms
Siena's Coat of Arms

Additionally they rode white and black horses,

giving rise to the Balzana,

or coat of arms of Siena with a

white band atop a dark band.

Some claim the name Siena derives from Senius. Other etymologies derive the name from the Etruscan family name Saina, the Roman family name Saenii.

We recommend visiting:

  • Siena Cathedral (Duomo) a 12th century masterpiece of Italian Romanesque-Gothic architecture.

Duomo Siena Cathedral
Duomo Cathedral Siena

  • The Sacristy and Piccolomini library have well preserved Renaissance frescos by Ghirlandaio and Pinturicchio respectively. Other sculptors active in the church and in the subterranean baptistry are Donatello, Lorenzo Ghiberti, Jacopo della Quercia and others.

  • MUST: The Museo dell'Opera del Duomo contains Duccio's famous Maestà (1308–11) and various other works by Sienese masters. Free entrance to the Facciatone with ticket entrance of the Museo dell'Opera.

Facciatone Museo dell'Opera
Facciatone, part of Museo dell'Opera

We recommend the Facciatone since it allows you to take exclusive pictures, with eagle-view vision over the Duomo, Piazza del campo and other noble buildings.

  • The Piazza del Campo, the shell-shaped town square before the Palazzo Pubblico with its tall tower Torre del Mangia. This is part of the site for the Palio horse race. The Palazzo Pubblico is a great work of architecture, houses yet another important art museum featuring Ambrogio Lorenzetti's frescoes depicting the Allegory and Effects of Good and Bad Government and also some of the finest frescoes of Simone Martini and Pietro Lorenzetti.

Following are some noble houses and buildings scattered around the city, entrance is free to most of them:

  • Villa Chigi

  • Castle of Belcaro

  • Villa Celsa

  • Villa Cetinale

  • Villa Volte Alte

We recommend eating at:

  • Osteria Babazuf, a recommended restaurant by locals. Good for traditional recipies and quality. It's expensive but necessary to understand what type of cuisine Siena has.

If you don't want to spend much we recommend eating at the opposite place called:

  • La prosciutteria, a local takeaway with small wooden tables out in the open, offering Tuscany's special food on the go, easy and inexpensive, perfect for the famous italian "aperitivo": grabbing some nibbles here and there to share accompanied with a glass of wine. Cheap, affordable, plenty of locals come here

Italian Aperitivo
Typical Traditional Italian Aperitivo

  • Eat takeaway food on corniche terraces draping from the surrounding walls of Piazza del Campo.

Trick: Go to Piazza del Campo > find the terrace you like > buy any food or wine from the bar, shop below > ask to go above to the terrace > enjoy the exclusive view of the Piazza

  • Enjoy aperitivo at bars out in the open in the main square Piazza del Campo. Be careful cause this is extremely expensive. You're charged a lot for food and drinks (it's normal when you're in the city center) but don't forget there's extra charges for service at your table. Example: you grab a coffee standing up, you pay 2 euros. You grab a coffee at the table, you pay 4 euros or more.

  • MUST: Take your food to the outskirts of Siena and have a wonderful sunset pic-nic

Location for pic-nic: Str. dell'Osservanza, 7, 53100 Siena SI, Italy

Palio di Siena Horse Race

The Palio di Siena is a horse race that is held twice each year, on 2 July and 16 August, in Siena, Italy. Ten horses and riders, bareback and dressed in the appropriate colours, represent ten of the seventeen contrade, or city wards.

The Palio held on 2 July is named Palio di Provenzano, in honour of the Madonna of Provenzano. The Palio held on 16 August is named Palio dell'Assunta, in honour of the Assumption of Mary.

A pageant, the Corteo Storico, precedes the race, which attracts visitors and spectators from around the world.

The race itself, in which the jockeys ride bareback, circles the Piazza del Campo, on which a thick layer of dirt has been laid. The race is run for three laps of the piazza and usually lasts no more than 90 seconds. It is common for a few of the jockeys to be thrown off their horses while making the treacherous turns in the piazza, and indeed, it is not unusual to see unmounted horses finishing the race without their jockeys.

  • The Piazza del Campo and Palio di Siena were scene to Quantum of Solace, the 22nd James Bond movie, directed by Marc Forster (2008).



Monteriggioni, Siena
The fort of Monteriggioni, Siena


Monteriggioni is a comune in the province of Siena in the Italian region Tuscany. The town is architecturally and culturally significant; it hosts several piazzas, and is referenced in Dante Alighieri's Divine Comedy. Strategically positioned outpost later fortified to be the first line of defense against the enemy neighbor Florence.

Elevation: 200 m

Population (31 December 2010) Total 9,165


Monteriggioni is a medieval walled town, located on a natural hillock, built by the Sienese in 1214–19 as a front line in their wars against Florence.

During the conflicts between Siena and Florence in the Middle Ages, the city was strategically placed as a defensive fortification. It also withstood many attacks from both the Florentines and the forces of the Bishop of Volterra. In 1554 the Sienese were able to place control of the town's garrison to Giovannino Zeti, who had been exiled from Florence. In 1554, in an act of reconciliation with the Medicis, Zeti simply handed the keys of the town over to the Medicean forces— considered a "great betrayal" by the town's people.

When to visit?

Monteriggioni di torri si corona Festival
Monteriggioni di torri si corona Festival on the first half of July every year

JULY 6th-7th-8th and JULY 13th-14th-15th - The medieval festival

one of the best festivals to attend, during the day and during the night you'll be enjoying Medieval re-enactments.

We recommend visiting:

  • The fortified walls and it's towers:

Fortified walls, totalling a length of about 570 metres and following the natural contours of the hill, built between 1213 and 1219. 14 towers on square bases set at equidistance, and two portals or gates. One gate, the Porta Fiorentina opens toward Florence to the north, and the other, the Porta Romana, faces Rome to the south. The main street within the walls connects the two gates in a roughly straight line.

The main piazza, the Piazza Roma, is dominated by a Romanesque church with a simple, plain façade. Other houses, some in the Renaissance style (once owned by local nobles, gentry and wealthy merchants) face into the piazza. Off the main piazza smaller streets give way to public gardens fronted by the other houses and small businesses of the town.

To visit the towers and walls you'll be paying an entrance fee of 3 euros per person that'll allow you to visit the walls facing the south, the ones facing north and the museum. Audio guides are also available.


We recommend eating at:

-Osteria Gelateria Antico Travaglio (Piazza Roma, 6/a, 53035 Monteriggioni SI, Italy) slightly overpriced but it's normal since it's in the main square. Food is very good and portions are generous. You won't be disappointed. Views of fortified walls, ancient buildings and the main church are a delight. Seating available also in the backyard of the Restaurant for a more relaxed and discrete enviroment.

Gallery :

5) La Speranza ( La Speranza, 53034 Colle Di Val d'Elsa SI, Italy )

Fiorentina steak La Speranza Ristorante
The Fiorentina steak, La Speranza Ristorante

By far my favorite restaurant for it's price and it's quality. Few tourists know about this place, mainly attended by local farmers, hunters, police officers, fire brigade, etc.

I've been introduced to this place by my father who took me here for my birthday.

Ever since that day, it has become my favorite place for food, specially the Fiorentina steak.

What is the Bistecca Fiorentina?

Bistecca Fiorentina is a T-bone steak of Chianina cattle . the steak is grilled over a wood fire, seasoned with salt, black pepper, and olive oil, applied immediately after the meat is taken off the heat. Thickly cut (about 3 fingers) and very large, often is shared between two or more persons. Traditionally served very rare, garnished with lemon wedges, accompanied by red wine.

6)Castles around our farm stay ( Str. della Villa, 7, 53035 Monteriggioni Loc. La Villa SI, Italy)

If you go to Tuscany you'll find castles scattered all over the place just like these ones. This one is B&B “la torre della signoria”. Walking distance is another castle called Castello della Chiocciola, named after it's spiral staircase.

Gallery :

7) Castellina in Chianti

castellina in chianti
Castellina in Chianti's alleys

Castellina in Chianti is a municipality of 2,800 inhabitants, located about 15 kilometres northwest of Siena. It is part of the Chianti Hills.

The first settlements date from the Etruscan age. In the early 15th century it became a stronghold, of which today the Rocca remains.

The city has remarkable roman and medieval details.

Tunnels surrounding the town have checkpoints with historical information to read. Little boutiques and shops sell delicacies such as olive oil, wine and porcini mushrooms, others selling local hand crafted leather.

Gallery :

On the same day, we recommend going to a wine tour to the famous Cecchi Winery at 15 kilometers distance from Castellina in Chianti.

8) Cecchi Winery @Foresteria Villa Cerna ( Località Casina dei Ponti, 57, 53011 Castellina In Chianti SI, Italy )

Since the 1980s, its growth has been constant and now has five estates, of which four are in Tuscany and one in Umbria. The wines that are produced are mostly with a designation of origin, for example the Morellino di Scansano, appreciated for its fruit and pleasantness; the Vernaccia of San Gimignano, produced in the historic estate of Castello Montaùto, owned by the family since 1988; and the Montefalco Sagrantino, the most important among Umbrian wines.

The main goal of the entire Cecchi Family production is to guarantee a wine of consistent quality, with a contemporary approach, which respects the original areas and enhances upcoming ones.

The wines of the Cecchi Family are wines that must be tasted and appreciated, and are a result of the meticulous work of many people that love and respect both wine and its territory.


Pay a visit and enjoy

  • A wine tour of the vineyards and line of production executed by a professional master sommelier

  • Wine tasting of 2 flagship wines and 3 premium signature wines

  • Coupling of wine with food (aperitivo with local cured meat and bruschetta)

  • Olive oil tasting

This and more at a modest price of 35€.

I've been to a wine tour in Napa Valley. Tasted 3 wines and few nibbles with hundreds of other tourists. Paid 70$ us dollars and I didn't feel the exclusivity at all.

Conclusion? Bargain.


Recommended wines:

Premium affordable wines (5-10€ each)

  • Cecchi La Mora

  • Cecchi Morellino di Scansano

  • Cecchi Vernaccia di San Gimignano

  • Cecchi Chianti Classico Riserva

Flagship Wines (20-45€ depending on the year can be higher in price)

  • Cecchi Coevo

  • Cecchi Brunello di Montalcino Enjoy your holidays and stay, and we hope this Travel guide helped you!

If it did, don't forget to share it with your friends, boyfriends, girlfriends, cousins, whoever you want! Visit Italy!

Thanks for reading!

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