Siena is a great place to centre yourself while exploring the city and its surroundings. You can cycle the local area, walk the vineyards or visit other nearby medieval towns like Monteriggioni, San Gimignano and Certaldo or Montepulciano like we did.
The old historic town of Siena with all of its characteristic cobbled alleys and piazzas hidden around quiet corners are amazing. There are the countless churches, all notable and impressive in their own way; museums, art galleries and other unique medieval buildings; enough to fill your interest for years. Then there is the shopping. Artisan retailers whether foodie, crafty, fashion or wine….restaurants or bars for every budget. It’s all here.
We stayed about 2 kilometres outside of the Siena historical city centre (7 mins by a regularly scheduled bus which stopped right outside our hotel). The room (Hotel Anna-Siena Nord) was quiet, modern and clean. It included a very good breakfast and at an excellent price. We stayed 8 days.
Our first day hike outside the city was from Monteriggioni back to Siena which we reach by bus. This tiny beautifully preserved 13th Century medieval jewel is built on a hill-top – what else! It’s on Leg #32 of the Italian Via Francigena pilgrimage to Rome. The end of the walk enters Siena at Porta Camollia. We continued through the streets to Port Romana where the next leg of the pilgrimage begins. We’ll make a mental note of this one for a future walk.
Our next hike took us from the magical town of San Gimignano to Certaldo. San Gimignano is an extraordinary preserved medieval city. It stands 334 metres above sea level on the site of a small Etruscan settlement dating back to the 2nd century BC. The town is famous for its many towers which make it easy to spot from miles around. We walked around the walls to enjoy the panoramic views of the farm land below before we begin our trek to Certaldo.
We make our way along the winding roads through the hundreds of acres of vineyards and past the olive groves until we reach the charming (and under-rated) medieval town of Certaldo approximately 15 kilometres away. From here we take the train back to Siena. We end the day on our balcony with a delectable plate of antipasti from the local market and a bottle of Chianti Classico…Mmmm. Delicious!
Our last outing from Siena was to Montepulciano; another must-see town. We took the train from Siena to the Montepulciano train station which is actually about 10 kilometres below the hilltop town. From the station there are buses that run to the top of the town.
Just when you think you can’t find any town more beautiful than San Gimignano, you’ll find this gem. Montepulciano is perched 600 metres above sea level on top of a limestone ridge. The views across the Tuscan landscape are beautiful! But as you pass through the gates that lead inside Montepulciano, you are delighted by the winding cobblestone streets past Renaissance buildings, palaces, and fabulous churches.
The regional artisan and specialty shops will tempt you at every turn. This area is known for its red wines, the most famous being the Vino Nobile di Montepulciano which are considered to be the best in Italy by many wine connoisseurs.
We toured one of the local wineries and then feeling all foodie inspired, went for an amazing lunch at La Pentolaccia where we had an outstanding bottle of Vino Nobile di Montepulciano along with an appetizer plate of local mixed cured meats and local Pecorino cheese – outstanding!
If we had more time, we would have taken the bus from Montepulciano to Pienza which is on the next hilltop. This is a great hike following the panoramic road to Montepulciano, dotted with cypress trees; the guardians of the Val d’Orcia. Oh well…next time.
Instead of taking the bus back to the train station, we decided to walk the 10 kilometres back through the vineyards and olive groves – another amazing day.