Special shout-out to my husband and favourite travel partner who has taken most of our travel photos.

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Siena & Tuscany itinerary in 3 days

Hotels

Siena:

Palazzo Ravizza Hotel

♥♥♥♥♥

This hotel was a great base for touring Tuscany. It is a charming hotel in the centre of Siena, sitting right by the old walls. It has nice, simple and clean rooms but the highlight is the tiered garden with breathtaking views of the Sienese countryside. These gardens are the perfect spot for a glass of wine before dinner and for the sumptuous daily breakfast. Ask for a room facing the gardens.

Guides and Tours

Siena and Tuscany:

Tours by Roberto. Roberto and his staff offer wonderful private or small group tours through the Tuscan countryside, including wineries, hilltop towns and historical sites. They offer pick-ups and drop-offs from most hotels.

Email: toursbyroberto@gmail.com

Phone: +39 328 425 5648 

Siena and Tuscany

 

Although Florence is the capital of Tuscany, we decided to move a little further south to the city of Siena and make that our base for exploring the Tuscan hill towns and the Chianti countryside. 

Tuscany, in central Italy, is known for its beautiful landscapes, eucalyptus trees, vineyards and mountains. With a population of approximately 18,000 people living within the walls of Siena - this mid-sized hill town is thriving and offers lots of things to do in the old town, as well as many delicious restaurants. Siena is an easy city to walk - it is compact and you can get almost everywhere within a nice, 15 minute stroll. The centre of town is pedestrian friendly, and in the evenings the town comes alive with many locals and tourists wandering the streets, squares and enjoying the restaurants.

Day 1

Afternoon

We arrived at our hotel, Palazzo Ravizza, a charming hotel in the centre of Siena, sitting right by the old walls. It has nice, simple and clean rooms but the highlight is the tiered garden with breathtaking views of the Sienese countryside. These gardens are the perfect spot for a glass of wine before dinner and for the sumptuous breakfast served daily. 

We went for a walk through the streets of Siena and stopped at a little sandwich shop for lunch. We bought sandwiches and a small bottle of Chianti, red wine wrapped in a traditional straw basket. We stood outside leaning against a bar table and enjoyed our lunch and people watching.

After lunch we strolled down to the centre of town to the main square, Il Campo. This is considered by some to be the best medieval square in Italy, and rightly so. It is in the shape of a sea shell, with City Hall and it's skinny tower located at the flat-shaped end. It is not unusual to see people sprawled on the ground around the palazzo relaxing. 

From there we walked up to see the Piazza del Duomo and the Duomo which sit at the top of a hill. This Duomo was originally built in the 13th century with a Romanesque style lower level and a Gothic style upper level which was built a century later. The inside is Renaissance style with plenty of frescos, sculptures (including a Michelangelo and Bernini) and an incredible library. 

We walked up the Duomo's tower for some breathtaking views of the Sienese countryside.

The piazza also includes a large building that once housed pilgrims and in more recent times was used as a hospital. There are often interesting exhibits within this building.

Evening

After a rest we went out to the hotel gardens to enjoy a bottle of wine before heading out to dinner.

We were lucky to be in Siena during the Contrade - a festival celebrating Siena's 17 neighbourhoods - and the Palio di Siena, a horse race where the neighbourhoods compete in various races. The festival culminates in a colourful parade where representatives of each neighbourhood march in their "team" attire. This evening we lined up along the streets with the crowds to watch the parade. 

Day 2

 

Day trip

Over the next two days we did day tours in Tuscany through Tours by Roberto. Roberto and his staff offer wonderful tours through the Tuscan countryside, including wineries, small towns and historical sites. They picked us up and dropped us off at our hotel.

Today we went on a tour of the Montagnola region where we visited a beautiful hilltop town with narrow streets and alleys. The panorama views going up to this town and from above were breathtaking. In town we went to see an artisan who makes stemware out of fine lead crystal.

From there we drove to another small town with a little-known Roman bath and spring. We had a delicious, rustic lunch at a local restaurant where the owner-chef is also a poet who writes about his love for Chianti wines. We heard a recital by the chef which was very charming. 

We then visited the unique, sacred 12th century Gothic cloister of Torri. Constructed in black and white marble, its decorated with a mixture of pagan and  sacred art.

 

From there we visited the evocative 13th century abbey of San Galgano, with its hauntingly elegant Gothic-style structure. Its roof missing, the sky serves as ceiling and the grass the pavement.

All the while, the views of the Tuscan hills, farms and vineyards were magical.

Evening

Back at our hotel we had a rest and went down to the garden for a glass of wine before heading to dinner. 

Siena is known for its sweat treat called panforte. This delicious and chewy concoction is made of honey, nuts and dried fruit. On Roberto's recommendation we went to one of the best spots in Siena, Pasticceria Bini - family run and all home-made.

Day 3

Day trip

We began with a panoramic drive through the Montepulciano area en route to the Chianciano area. Here we visited a private museum of Etruscan finds, run by a club of archaeological enthusiasts of which Roberto is a member. The Etruscans were the original inhabitants of this area.

After learning of the history of the Etruscans we also visited a recently excavated

Etruscan tomb not far from the museum.

We then drove through the Val D'Orcia passing stunning fields of sunflowers and eucalyptus trees. We stopped at an organic farm where after an introduction to organic farming, and a pecorino cheese-making demonstration, we had a lunch based on fresh products cooked by the family which owns the farm.

After lunch, we drove to the hilltop town of Montepulciano where we visited Cantine Contucci, one of the oldest wineries and cellars in the region where the family has been making wine for over 1,000 years. We got to taste and purchase this delicious wine. We walked through the city and met one of the last seven coppersmiths in all of Italy, who shared his passion and crafts by giving us a demonstration of copper shaping.

Evening

We walked out for dinner on our last night in Siena after enjoying our wine in the garden.

Day 4

Morning

After breakfast we checked out of our hotel and took a bus to Rome.

 
Guides and Tours

Siena and Tuscany:

Tours by Roberto. Roberto and his staff offer wonderful private or small group tours through the Tuscan countryside, including wineries, hilltop towns and historical sites. They offer pick-ups and drop-offs from most hotels.

Email: toursbyroberto@gmail.com

Phone: +39 328 425 5648 

Itinerary Add-ons

This itinerary can be combined with: