5 days in Tuscany – My favourite spots

I have always wanted to go to Tuscany. It´s one of those dream destinations that you already have that perfect picture in your head. I´ve read many books or watched movies that were set in Tuscany. I imagined it like a peaceful place, where time stops, with old beautiful houses, golden light, fantastic food and of course the famous green hills with cypresses.

A trip to Tuscany

Last year in May I finally made my dream happen and went on a roadtrip with my boyfriend for 5 days. We booked our flights from Berlin to Pisa (Ryanair & Easyjet) and rented a car. We arrived on a Wednesday early evening and directly left Pisa (I´ve been to Pisa once and we wanted to leave some time for it at the end of the trip) towards Lucca. It is a 45min drive to Lucca.


Where to sleep

We booked one night at the Bed&Breakfast Dolce Sosta (Website). Dolce Sosta is located a little bit outside of the city (4km to the centre), but with a car it´s not problem. The B&B was a great choice. The owners are very welcoming and helpful hosts. The rooms are simple, but decorated with taste and in bright colors.

My highlight of Dolce Sosta was to have breakfast in the beautiful garden the next morning. The sun was shining and we had this beautiful view! A first taste of Tuscany :). The breakfast (for Italian conditions) was really good too (cooked eggs, cheese, ham, bread, of course great coffee, juice, fruits, cake and cookies).



Lucca is famous for it´s ring shaped square Piazza dell’Anfiteatro. It defnitely is a lovely square with cafes where you can enjoy a coffee while sitting in the sun. I recommend to visit the square in the early morning, when there a no tourists (first of all for the better pictures without people, but also for the “local” atmosphere).

Afterwards we visited the Torre Guinigi, a tower with oak trees on it´s top! The view is stunning and absolutely worth to climb up the steps! You can see the whole city. It was my highlight of Lucca for sure!


La Tana Del Boia  (Facebook) was my culinary highlight in Lucca. It is a small bar that offers incredible tasty meat & cheese platters and delicious panini & sandwiches. We had dinner there and ordered a mixed platter with different types of salami, ham, Mortadella (I love Mortadella!!) and a variety of cheeses.  The cheese had different flavours such as truffle (my favourite) or pepper and was served with marmelade and truffle honey. I was in heaven! Seriously, what do you need more? The quality of the food is fantastic! Please go there, if you are in Lucca!

For me it was the first time I tasted honey with truffle and I absolutely loved it. When we walked through Lucca I discovered a truffle shop and bought the honey and some pasta sauces to take home.


After Lucca we made a quick stop in Florence. People might hate me if I say that I don´t really like Florence, but I can´t help it, that´s the truth! I have been to Florence already once some years ago so this time was my second visit. Both times I got really stressed of all the people. You cannot really enjoy the city or get it´s charme because there are tourist crowds everywhere! I thought it was maybe just my sensation but my boyfriend said exactly the same. I mean, the Florence Cathedral of course it´s beautiful, but again too many people!

We found a peaceful little (quiet!) oasis at the cute cafe Amblé (Website) that offers organic juices and yummy sandwiches. We rested for a while and decided to leave the hectic Florence asap towards our next stop.

Figlinie Valdorno & Arezzo

Where to sleep

After arriving from Florence we checked in at the B&B Le Vecchie Mura (Website). It is a cute B&B with basic but cosy rooms, huge balconies and a terrace with nice views towards the old town. We had a walk afterwards and discovered the town Figlinie Valdorno. Apart from the square there is not so much to see so we decided to have an Aperol Spritz at one of the square bars and to discuss what to do with the rest of the day.

Figline Valdorno

We decided to spend the evening in Arezzo (about 40km away). I only read once about Arezzo in a travel guide and didn´t really have an idea about it. It turned out to be a wonderful surprise. Arezzo was one of the most beautiful cities of our trip for sure and it has a great medieval atmosphere! At night the sights of the city were illuminated with colored lights and I really enjoyed walking around.


We found the Trattoria il Saraceno (Website) that offers typical Tuscan cuisine. As a starter we orderd a plate with  cheese and roasted bread slices with olive oil and truffle paté. I love truffle, I cannot get enough. Even though my boyfriend (and he was a truffle lover before this trip) said, that after Tuscany he needs some “truffle-free” time. Haha.


Panzano in Chianti

Panzano in Chianti is a tiny village that might not even be listed in many Tuscany travel guides. To me this cute village had more charme than most of the famous Tuscany places (that in the end most of them look the same). There were not so many tourists in Panzano which ranked it higher for me. And finally I found what I had in mind when imagining Tuscany: A peaceful atmosphere, beautiful landscapes and a feeling of time stopping. We had a lovely walk and found a church, a sundial and some cafes/bars that were not busy at all.


Where to sleep

We stayed one night at the Villa Rosa Di Boscorotondo (Website) a bit outside of Panzano. It is a beautiful historic villa with antique & authentic furniture, surrounded by vineyards and a charming, wild garden (with cypress trees :)!). There even was a fountain in front of the entrance! Parking is provided and free. It was just hard to find the place. We took a rather adventurous street over a field until we realized “this cannot be the way”. Luckily we found a local in the end that was so nice to guide us.

We were lucky a second time and got a better room with a huge terrasse. We had a sun bath with mountain view, wow! The room itself was spacious and equipped with a romantic wrought-iron bed. Breakfast was not included in our rate.



We had an amazing dinner at La Cantinetta Di Rignana (Website) about 25min drive from the hotel, set in the middle of vineyards. The restaurant had very good reviews which convinced us to give it a try. The landscape is gorgeous as is the restaurant that looks like a farm with the typical Tuscan brick walls and nice decorations. The food was excellent. We ordered buffalo mozarella with salad, dried tomatos and parmesan as a starter, followed by truffle pasta (again haha!) and a great Tiramisu with berries at the end.



Sienna was one of my Tuscany highlights as well. What a gorgeous city (even if more touristic and not so peaceful ;))! I was especially in love with the Piazza del Campo square. We had the perfect weather, tried some delicious ice cream and discovered the city walking for some hours before continuing to the next destination. I would have liked to stay one night in Sienna, since I imagine it very beautiful at night.



Next stop after Sienna was Montepulciano. Unfortunately shortly after arriving it started raining a lot but at least I could take a picture of the fountain at Piazza Grande. We discovered the Art Deco Caffe Poliziano (Website) that was established in 1868. It was restored to the original setting 20 years ago. What a shame we couldn´t sit on the tiny balcony with wineyard view since it was still raining. We took a coffee inside instead (expensive but still worth because of the antique setting).



We found the restaurant L’Assassino (The Fork) when searching for a dinner place with one of my favourite apps “The Fork“. The Fork offeres discount for restaurants. We got a 50% discount for L’Assassino. Only condition is that you´ll have to take at least 1 starter, 2 main dishes and 1 dessert with 2 people, which totally is ok :). The reviews were super good and it was only 15min away from Montepulciano in the little village of Chianciano, so we decided to go.

L’Assassino in the end was the best restaurant of all Tuscany. The excellent service, the perfect presentation of the food, the high quality of products and the nice decoration were outstanding. I even got a little extra chair for my handbag (which happened to me only one time before in the fancy Armani Hotel in Milan).

We had a fantastic dinner and I would definitely come back. With the discount it was incredible cheap and we felt almost guilty for getting such an amazing dinner for around 20€ per person (including starter, main, dessert, wine, drinks and coffee!!). When we left the restaurant we told the nice lady that runs L’Assassino that it definitely was our best meal during the whole trip and that we absolutely loved it! I hope she reads this article one day :).

San Gimignano

Where to stay

We stayed one night at Il Castagnolo (Website), 3km outside of San Gimignano city. It is a beautiful country house in typical Tuscan style. Il Castagnolo has a nice garden with pool and cypress trees (standard ;). The B&B is surrounded by wineyards which invited us to go for a walk.

The rooms and the whole B&B is decorated in shabby chic design with lots of cute details that were arranged with love. Our double room was spacious and equipped with a white wooden double bed and a little canopy on top.

The breakfast next morning was lovely with lots of options (fruits, musli, cakes, eggs, bread, …).


Before going back to Germany we spent some hours in Pisa to see the Leaning Tower of Pisa and to have some lunch. In my opinion there is not so much more to see in Pisa other than the tower.



We found the cool cafe Keith Art Shop Cafe (Website) in Foursquare (my favourite app to discover new cafes & restaurants). The cafe is located opposite of the graffiti wall of artist Keith Haring and is named after that. I had a Parmigiana, it´s an Italian dish (similar to Lasagne) with layered aubergines. It´s one of my favourite dishes and it was one of the best ones I had.

After lunch we returned to the airport to go back to Berlin.

Some advices

  • Car Rental: Make sure you have enough limit on your credit card when you pick up the rental car. It happened to me once in Italy that the car rental company wanted to block 4000€ as guarantee (and of couse I didn´t have so much limit, had to call my bank and was lucky enough to reach someone to solve the problem!).
  • Driving in Tuscany: We got 2 fines some month after the trip. Both times we entered a wrong street (touristic zone) in Florence and in Sienna as well. We saw the signs too late and were already recorded by camera. We paid more than 300€ for those 2 fines :(. That really hurted!
    In Pisa driving can be a little tricky. We almost had an accident on the way to the airport. Drive carefully!
  • Hotels: Make sure to book your hotels in advance. When I started planning the trip I wanted to just book the flight and find nice B&B or hotels on the way. Luckily I checked before just to get an idea and most of the places where almost fully booked already. Depending on the season hotels can get very expensive. In the end I planned the whole trip and booked all the places. We spent between 40€ and 70€ per room/night.


It was a nice trip to Tuscany but somehow I was a bit disappointed sometimes. I had imagined it better and didn´t like the tourist crowds that disturbed “my picture” of the peaceful place I had in my mind. Maybe it´s worth to go off season or more to the country side and rent a nice villa. In my opinion there are better places in Italy. For now I wouldn´t go again but I still love truffle though :).

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About Me

Hi, I am Steffi. Welcome to my blog myfaves! I am 33, B2B Field Marketer in a software company and spare time blogger by heart. My home base is Berlin Mitte since 2 years. Before Berlin, I lived 7 years in Cologne and 5 years in Hamburg... Read More


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