I’ve never thought I’d ever play tourist in Italy. Because I’ve spent every summer in Tuscany with family, I felt I knew the area so well, I didn’t have to return as an adult.

Well, and so it seems that I have met the one person to travel with that hasn’t been to Florence yet. Not to mention Siena. So it just happened, a couple of weeks ago, that I rediscovered the beauty of it all on our road trip through Tuscany. Because there are no direct flights to Florence from Hamburg, we decided to start off in Pisa. Again, I’ve been to Tuscany many times – so I didn’t do “the obvious”, but visited spots off the beaten path. Check out our route here.



I have very fond memories of this little town, north of Pisa by the sea. A Tuscan vacation spot by the book. The charm of this town is not really in its beach, but the view of the mountain backdrop, where the famous Carrara Marble comes from. More so the atmosphere in the evenings, when all the lights at Luna Park go on, little boys take their electric Batman-car for a spin and girls cheer from pony-drawn carriages. Luxury boutiques invite for late-night shopping sprees and everyone is just relaxed. Perfect to start your trip!


Although Forte dei Marmi might be a nice town to stroll around in the evenings, I do recommend you stay the night at Pietrasanta. It is known to be an artistic little village at the foot of the mountains. It’s surprisingly busy in the evenings too, lots of cute little streets lined with restaurants. A town definitely not to miss out, and maybe a better option to spend the night if you’re not willing to pay the high prices that are common in Forte dei Marmi.


The town is located an hour and a half or two hours drive through Tuscan hills and beautiful landscapes, famous for its fort-like resemblance and big city wall. You can find some of the oldest buildings in Tuscany here, definitely worth a visit and a quick stroll through – maybe lunch break before your next stop.

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From the place where I spent every summer as a child, we had an awesome view of the “city of towers“. This place will always be special to me but I’m sure you will get the same feeling when you wander through the steep little streets in the evening light. Pay attention to the way there, you’ll get some pretty nice opportunities to see the city from afar.



The city that surprised me the most. I guess from our house it was always just a little too far to go and spend an evening there, but I absolutely fell in love with Siena this time. We stayed in a very cute hotel Podere La Strega (, just outside the city with a pool and excellent views.

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For dinner, there I can recommend Osteria da Divo (, just maybe ask for a table that’s not all the way downstairs. You’ll understand once you’re there. During the day we took a day trip to Greve (read more about this below) and returned, but you can easily plan the next stops into your route on the way up to Florence.


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We visited Siena in between the two Palio races, the whole city was filled with people waving their flags cheering for their houses.
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Monday in Italy 🙂

Beautiful Duomo di Siena – one of my favorite buildings!


A perfect stop to plan a lunch or dinner. For lunch, head to La Bottega di Volpaia (www.labottegadivolpaia.itfor one of the best Tagliatelle al Ragu con porcini that you will ever have. For dinner I recommend you book a table at Osteria Volpaia (


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The drive from Volpaia to Greve is stunning in its own way. The Tuscan landscape changes all the time, the Chianti area is obviously lined with vineyards and old mansions tucked away in the hills. In the small town of Greve, you will find a beautiful central market place and the gourmet butchers shop Macelleria Falorni ( where you can get the best Salami Tartufo and wild boar salami. And I really mean that when I say THE BEST!




Restored only some 3 years ago, sure this Wine Estate is world famous for its wine and restaurants – but you have to see the architecture! It’s conveniently situated right next to the high way, so you can easily make your way up to Florence.


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Ok first of, please buy yourself a guide book. There is no way I can even begin to explain history or cultural facts about this city. I’ll give you some recommendations, which I wish I had when we did the tourist thing there: plan everything beforehand. I know it sounds lame and everyone nowadays hates to commit to a fixed date and time, but do yourself the favor and do it this one time – if you plan to visit naked David at Galleria dell’ Accademia, Palazzo Vecchio, Palazzo Pitti, the Uffizi gallery or the Dome.

If you want to enjoy a view from above, then you can save some time and head up the Campanile tower, instead of the Dome itself. There’s no elevator and there are tight spaces on the way up. But the view is worth it – fewer people line up here so it went really fast.

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The view from the Campanile Tower

Another pretty good spot is located, no not at Piazza Michelangelo, but at the Bardini Gardens ( There’s a small café on top, no crowds and an excellent view over Florence.

We stayed at Hotel Garibaldi Blue (, which is on Piazza di Santa Maria Novella, a cute little square lined with restaurants. For dinner, I can recommend you try the area across the river. Trattoria Napoleone ( has good Pizza and is very cozy inside. If you’re there in summer, make sure to check festivals or concerts in the area – we were lucky to see Jamiroquai live at the Hippodrome Visarno!

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View from Gardino Bardini


After San Gimignano, this town is definitely my favorite in Tuscany. Plan in a few hours to stroll through the pedestrian streets or rent a bike to take a ride on the city wall and enjoy a delicious Gelato!

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Soft hills lined with cypress trees, that’s Tuscany.


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All photos: Jessie Schoeller


  1. Jessie Schoeller

    I do too… I think you’ll be fine in early June, if you use data roaming just use or google maps and just call the locations in the way. It’s much easier to be spontaneous these days

  2. Mark Skrotzki

    Enjoyed your article. Can you tell me if you can travel through this area in EARLY JUNE without hotel reservations and have a good chance of getting a room every night? We like to wander and not have a fixed spot every night.


  3. Dav

    I love the pictures! One of my favorite movies is “Under the Tuscan Sun”, and I have yet to experience Italy for myself. These are great! Someday!

  4. Rachel Lishman

    Wonderful photos that remind me of my recent trip to Florence. Much the opposite of you, I only got to spend an afternoon in the Tuscan hills, but loved every minute. If the ‘must sees’ are that good, I can only imagine how excellent a trip off the beaten path must be! 🙂

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