5 Days in Tuscany, Italy

Tuscany was absolutely amazing–the culture, the food and wine, the vineyards and the cute medieval towns. I think 5 days is not enough to see every thing but it does give you a chance to experience Italy at its best. I am sharing my itinerary from the trip.

Day 1 & 2: Florence

We spent our first two days in Florence. We decided we will explore some major highlights and also leave sometime to just walk around the beautiful city.

View from Giotto’s Bell tower!
Sunset at Piazzale Michelangelo

Day 3: Agriturismo

We picked our car from Florence and drove to Impruneta, a small Tuscan town 45 min away. Our gorgeous farmhouse or agriturismo, tucked away in the midst of vineyards and olive orchards, was perfect for relaxation. Everything at breakfast was locally produced. The owners produce their own olive oil which was delicious! We went into Impruneta town centre for a quick lunch. Dinner was at the pretty and romantic Tre Pini, a family run restaurant. I tasted the freshest and most amazing tomato sauce here!

Our Tuscan Farmhouse– Podere Scaluccia

Impruneta street scenes
Impruneta city centre

Day 4: Day trip to San Gimignano

We drove to Guardastelle in Val D’Elsa for Tuscan lunch and wine tasting with a small group. The drive to the vineyard was so beautiful with rolling hills and greenery as far as the eye could see. Guardastelle is a small family-owned vineyard near San Gimignano. Apart from producing very small quantities of red and white wine, they also produce olive oil. You need to book a slot for wine tasting and lunch and they also have cooking classes. My favourites were the ribolita (a lentil and bread soup), bruschetta with generous portions of olive oil, and Vin Santo (dessert wine) with cake and biscotti. I especially liked the local white wine aka Vernaccia di San Gimignano, and this is from somebody who is not a big fan of white wine!

After lunch, we went to the beautiful town of San Gimignano. It’s a walled town and you can’t take your car inside so you need to park at one of the squares outside. We walked around a bit, taking in the beauty, looking at cute shops selling trinkets, smelling the aromas of Tuscan cooking from tiny cafes and just savouring the slow life for a bit.

The main Piazza with the well in the centre

San Gimignano is called the Manhattan of Medieval ages because of its many towers! Once home to multiple rich families, there was a competition of sorts to see who builds the tallest one and quite a few of those still survive. I went up the Torre Grossa, the tallest tower in town, and the views were stunning. I was up there was quite sometime–the view, the breeze and the church bells chiming were so mesmerizing. You can get a ticket to the tower, the museum and church from the same counter behind the Church. The climb was a bit tiring so I sat down for a quick coffee at the cafe in front of the Church where my husband was waiting for me.

View from the top of Torre Grossa

San Gimignano Church
Frescoes inside the Church

There was no way we were going to miss Dondoli’s award winning Gelato while we were in the town. Despite the queue, it’s totally worth it for the amazing flavours. Before leaving, we packed take away pizzas from RiccaPizza. Driving back turned scary towards the end because we got lost a bit but finally reached our farmhouse safely!

Day 5: Siena

We spent a night in Siena. I am still undecided whether Siena was my favourite Tuscan town or San Gimignano. I think I will go for Siena because it’s got such a rich cultural and architectural heritage. Read about how I spent a day in Siena here.

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