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How to Spend Two Nights in San Gimignano – The Italian Diaries

I first visited San Gimignano a few years ago, and instantly fell in love with its location (in the heart of the Tuscan countryside), its quaint and historic walled city, and its authentic Italian vibe.

So, when Tim and I decided to book a trip to Italy to rest and revive after such an intense year, I said to him we had to go to San Gimignano. I really wanted to show him how beautiful and picturesque it is, and was also dying to take him to this incredible restaurant my cousin and I stumbled across all those years prior (a place I told him was the best proposal spot, ever!).

 

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We’ve had huge interest in our Italian trip, so I’m going to share a day-by-day diary of what we did and where we went, first starting with our stay in San Gimignano.

So, if you are in need of some San Gimignano tips, you’ve come to the right place.

If you have any questions at all, or want to share your advice on this beautiful area in Tuscany, don’t hesitate to pop them in the comments below.

E. Xx

 

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Day One:

10.00am – We arrived at Pisa Airport after a two hour flight from Manchester, and went to pick up our rental car, which we ordered from Maggiore before a few weeks before our trip. We decided to spend a bit more money on the car, rather than choosing the cheapest possible version, as we wanted to feel safe on the windy Tuscan roads. We ended up receiving a VW Golf, which was brilliant, and actually quite luxurious.

2.00pm – We arrived at our hotel, Hotel Casolare Le Terre Rosse, located in San Donato, about a 15 minute drive from the main San Gimignano town. It was only an hour an a half drive from Pisa to the hotel, but we took a little longer to get there, as we wanted to stop off at some places on the way. The drive was surprisingly really easy, although driving on the other side of the road can take some getting use to. We had some practice of this when we went to the French Alps at the beginning of the year.

 

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3.00pm  – We were starving as we hadn’t eaten since 6am, so decided to head to the local winery, Fattoria San Donato, which is just 100 metres down the road from our hotel. My cousin and I had been to this family-run fattoria in the past, and I remember being provided with an incredible spread of cheese and antipasto while we tasted wine. So I said to Tim let’s go there to get something to eat. However, only wine tasting seemed to be on offer when we arrived, which, hey, was totally fine with us. I now have a feeling my cousin and I had booked in for a different kind of experience last time, so perhaps call and ask before you go.

The wine tasting was fantastic. We tasted a variety of Fattoria San Donato’s own wines, including white, red and their dessert wine, vin santo, all of which were delicious. Their pricing is super cheap too – around 7.50 – 15 euro for a bottle.

 

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4.00pm – We headed back to our hotel and enjoyed a few Aperol Spritz by the beautiful pool area, it was bliss. At the hotel they make the Aperol Spritz with just Aperol and Prosecco… without the soda. If you’re game to try, I have to say this is the best way to make an Aperol Spritz. Yes they’re a little stronger, but they are full of flavour!

 

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7.00pm – After our relaxing, and slightly tipsy, afternoon, we were more than ready for dinner. We decided to have dinner at the hotel’s restaurant, which is located in a lovely courtyard. I had a vegetarian lasagne, Tim had a chicken dish, and we shared some bread drizzled with Italian olive oil (like wine, Italians do olive oil best) and sipped on some Italian white wine. For dessert we had traditional dish, Cantucci e Vin Santo, which is a glass of vin santo served with almond biscotti, yum!

 

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Day Two

10.00am – We enjoyed a leisurely buffet breakfast at our hotel. Not going to lie, our heads were pretty sore after all the drinking we did the day before, but it was nothing a good Italian breakfast couldn’t fix. The hotel has an array of bits to choose from, including cereal, fruits, cheese, salad, bread, pastries and Italian cakes.

11.30am – We headed off on a road trip to Siena, which is about an hour away from San Gimignano. Once we arrived, we parked outside the town and made our way in by foot. We found a delicious gelato store, and were so excited! Only 4 Euro for the biggest gelatos we have seen – a delicious and nutritious lunch. I chose a Nutella flavoured ice cream, which had real Nutella in it and hazelnuts, it was absolutely to die for!

My tip for finding authentic and cheap gelato in Italy – Always look for places down side streets, away from the main tourist attractions.

As we had limited time in Siena, we only were able to have a quick walk around. We saw the outside of the Duomo, but if we had our time all over again, we would have definitely gone in. It is apparently breathtaking inside, even more so than the outside, which is pretty spectacular.

We also went to the impressive Piazza del Campo, where the Palazzo Pubblico lies, and window shopped down the cute little streets.

 

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5.00pm – We headed to San Gimignano town to have a walk around before dinner. As we were short on time, we didn’t manage to go to any of the churches or museums, but this didn’t matter to us, as we loved simply walking around the beautiful town.

6.00.pm – It was time for ‘that’ restaurant. I had been raving to Tim about Le Vecchie Mura ever since we met, so he made a reservation there about a week before we arrived in Italy. To ensure you get a table next to the railings on the terrace – this is the best spot to sit if you want to enjoy the panoramic view of the Tuscan countryside while you wine and dine – make sure you book!

We shared mixed bruschetta to start, and for mains, I had mushroom pasta and Tim had rabbit. We were both impressed with our meals, however I had the arrabiata pasta last time I dined at the restaurant and I really loved it. Even though the mushroom pasta was great, I think if I went back, I would choose the arrabiata instead. After our headachy morning, we wanted to have something light to go alongside our meals, so chose bottle of dry prosecco. For dessert, we shared a lemon tart and lemon gelato, both of which were fresh and yum.

Le Vecchie Mura is honestly so beautiful. The setting is so romantic and the meals are surprisingly not pricey (we spent about 70 Euro), considering the large portion sizes and the too-good-to-be-true scenery.

 

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9.00pm – We stayed at the restaurant to watch the sunset and then decided it was time to go – we had hogged the best seats in the house long enough. We had another walk around San Gimignano town, which was absolutely beautiful to see lit up at night.

We made it back to our hotel, where we sat out in the courtyard, had an Aperol Spritz night cap and watched the stars, it was so beautiful and peaceful.

 

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Day Three

11.00am – After another great breakfast at our hotel, we checked out and made our way to Fattoria Il Piano for a wine tour and wine tasting. We booked in for the ‘Estate Tour’, which was 28 Euro each, and included a tour of the vineyards, gardens and where they make the wine, and a comprehensive wine tasting, which included 7 wines (white, red and vin santo), and a mixture of Italian bread, cheese and antipasto.

The estate itself is absolutely stunning, and with panoramic views of San Gimignano, you could easily spend the day, relaxing here with a bottle of wine. It was such a beautiful sunny day, so we sat out on the terrace while we wined and dined.

All of the wines were spectacular, but I have to really recommend the Rosso Toscana Baciolo 2010, of which we took a bottle home, and are contemplating buying a case to send to us in the UK. It’s 100% Merlot and has a nose of rose and lavender flowers, tamarind and a touch of caramel, black pepper and mace. It was an ultra smooth full-bodied red, with a delicate mix of sweetness and savoury.

1.30pm – After a glorious afternoon, we finished our stay in San Gimignano on a high and made our way to our next destination in Tuscany, Villa Dianella. More on this soon!

 

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Wine Tasting at Fattoria Il Piano in San Gimignano, Tuscany, Italy
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Have you been to San Gimignano before? What are your favourite wineries and fattorias? Where did you stay? Xx

For more vacation inspiration and destination tips head to our travel section.

Latest comments
  • Omg these photos!! Sorry about the all caps — cant turn it off. I loved your engagement story on insta. It was so sweet. Thanks for sharing your journey with us

  • Ohh yes ! This town is so so beautiful! I was here actually Last weEkend, But only as a short stopover oF 1 h. Totally not enough as you can Imagine! Didn’t even have the time to taste world’s best gelato! Can’t wait to come here again and visit all the gorgeous spots in yOur pictures.!

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