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Florence, Italy
FIRENZE (FLORENCE) As the capital of the region, the beautiful city of Florence
is the perfect place to start your Tuscany road trip. Especially if you fly to
Italy and grab your rental car here. For me, Firenze is one of the most gorgeous
cities all over Italy. So spend a few days here to soak up the first Italian
flair, stroll through the old alleys, gaze at its historic monuments, have
amazing pasta, and of course, your first scoop of gelato! Here you can also find
one of the nicest places to enjoy the Tuscan sunset with an incredible view
across the city. To do in Florence: * Walk across Ponte Vecchio – the iconic
bridge with houses on it * Walk up to or take an e-bike tour to Piazzale di
Michelangelo for the best view across the city, especially for sunset when it’s
tinted in orange light * Join a free walking tour – to learn more about the
historic place * Visit the cathedral Santa Maria del Fiore – one of the most
beautiful cathedrals in Italy * Visit the Uffizi – the famous gallery showing
many of Da Vinci’s stunning pieces of art * Join a Chianti wine tour and
tasting – to try some of the best Italian wines in the gorgeous Chianti hills *
Learn how to make Pizza and Gelato – a unique experience at a farmhouse outside
of Florence
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Vinci, Italy
Does the name ring a bell? As we’ve talked about the ancient walls of Lucca
designed by the famous Leonardo da Vinci, you may have guessed it. Vinci is the
birthplace of Leonardo da Vinci and therefore definitely worth a day trip. A
gorgeous old town with steep alleys and a nice castle from where you can enjoy
the views across the beautiful Tuscan countryside. And of course, there’s a
great museum packed with da Vinci’s sketches and models of his inventions and
lots of info about the life of this impressive man. To do in Vinci: * Take a
stroll – Explore the steep alleys by strolling around * Walk up to the castle
Castello dei Conti Guidi – to enjoy the view on the stunning countryside * Visit
the Leonardo da Vinci Museum – What would be a visit to da Vinci’s birthplace
without learning something about him?
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Lucca, Italy
IN LUCCA, YOU CAN TAKE A STEP BACK IN TIME. LET THE HIGH MEDIEVAL ALLEYS CARRY
YOU BACK A FEW CENTURIES, AS YOU LINGER PAST HUGE SHOP WINDOWS THAT LET YOU
IMAGINE THE OLD, WOODEN GATES OF STABLES. RIGHT IN THE HEART OF THE CENTER, YOU
REACH A VERY SPECIAL PIAZZA WHICH IS NOT A SQUARE, BUT AN OVAL. CAN YOU GUESS
WHY? IT WAS BUILT RIGHT ON TOP OF THE RUINS OF AN OLD THEATER, THAT’S WHY IT’S
CALLED PIAZZA DELL’ANFITEATRO. But the real highlight encircles the city: Its
medieval, well-preserved city wall, designed by none other than the famous
Leonardo da Vinci who was born nearby (but we’ll get to that in a bit). You can
actually walk (or even bike) the whole historic 4 km all around Lucca. To do in
Lucca: * Visit Torre Guinigi – this tower gives you the perfect panoramic view
across Lucca with several old oak trees on top * Walk across the ancient city
walls “Mura di Lucca” – You don’t have to do the entire 4 km. And you don’t even
have to walk. You can rent bikes or just take a seat close to one of the gates.
* Stroll through the old, cobblestoned alleys to Piazza dell’Anfiteatro – as you
enter the oval-shaped piazza you get a hint of the feeling it must have been
entering the Roman theater * Acquedotto del Nottolini – Take a short walk
outside of town and admire this old aqueduct that used to carry water to the
town. The perfect photo spot!
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Pisa, Italy
Well-known for its failed landmark that then turned out incredibly famous, Pisa
has become a tourist magnet. The Leaning Tower of Pisa is one of Italy’s
best-known and also most visited sights. Did you know that the tower is actually
the bell tower of the dome next to it? So when you look at the tower, don’t miss
to turn around and gaze at the beautiful Dome Santa Maria Assunta. And here are
some more fun facts: Only a few years after the start of the construction the
tower started to sink due to the unstable soil. In an attempt to compensate for
the tilt, the upper stories have a less leaning angle than the lower ones. So
the tower is actually slightly curved. It hasn’t been allowed to climb the tower
for many years due to consolidation work. While the history and construction of
the famous tower are interesting, there are honestly much nicer and more
authentic towns on your Tuscany road trip. If you decide to visit Pisa, do it in
the early morning hours (before 9 a.m.) or late afternoon hours (after 6 p.m.)
to enjoy the place without the day tourist crowds. And don’t forget to take a
stroll through town and not just stop for the tower. To do in Pisa: * The Tower
– Make sure to get a Skip-The-Line ticket for the Leaning Tower * The historic
center – Don’t miss lingering through the winding alleys of the historic center
* The river – Take a walk along the river Arno * Outside of Pisa – Stop by the
Via del Gombo in Parco San Rossore, a beautiful cypress avenue
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Bolgheri, Italy
While the area around Bolgheri is well-known for its many vineyards, driving to
the small town is especially spectacular. You drive along Viale dei Cipressi –
an extremely beautiful avenue of centuries-old cypresses. Yet, fewer people
actually make it to the small town of Bolgheri itself. But don’t miss it, as
it’s a calm, genuine town where you can visit an old castle or sit in one of its
many taverns sipping delicious wine.
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Montepulciano, Italy
You may have heard of Montepulciano before. That’s because it’s not only a
Tuscan town but also a grape variety. But before sipping its delicious wine, get
enchanted by the gorgeous town. Located on a hilltop within ancient city walls,
you can only enter the town through one of two gates. But from here you get one
of the best countryside views on your Tuscany road trip. And the true magic of
Montepulciano lies under the ground: An impressive, old tunnel system that used
to connect the main palaces and is nowadays used as (of course!) wine cellars.
To do in Montepulciano: * Visit the underground city – to see its caves and
tunnels * Stop by the lovely Piazza Grande – the town’s main square * Join a
Vino Nobile wine tasting – such as the free tour and tasting by Azienda Agricola
Ercolani
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Siena, Italy
It’s for good reason that anyone who’s been to Siena raves about the unique
flair of this Tuscan city. Siena! A place to enjoy La Dolce Vita, sipping coffee
in one of the busy cafés. A place to marvel at medieval towers and brick
monuments that make for shady alleys. And to take endless strolls through the
UNESCO World Heritage historic center. It’s not hard to get lost in Siena. But
let’s be honest. This way, you will explore corners that you probably wouldn’t
have found otherwise. And the way this city is built will always find yourself
back in the main square, Piazza del Campo. If you could do only one thing in
Siena, then you should enjoy the view across the city’s roofs from the top at
least once! Both Torre del Mangia, and the Opera della Metropolitana, are great
places to do so. On your Tuscany road trip, be aware that you’re not allowed to
drive into Siena’s downtown. The fines are quite high. So look for the Italian
signs that look like a red stop sign, even if your GPS wants to send you
further. To do in Siena: * Climb up the 400 stairs of Torre del Mangia – for a
panoramic view across the city * Allow yourself to get lost – to take some time
to look at the small details on the historic monuments, such as the animals
marking which district you’re in * Take the marvelous “Porta di Cielo” tour of
the dome’s roof * Visit the Piazza del Campo – a busy fan-shaped square where
both locals and tourists like to spend time * Enjoy dinner in the Chianti
vineyards
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Monteriggioni, Italy
If you stay in Siena for a few days, Monteriggioni makes up for a great day trip
or a nice stop during your Tuscany road trip. Overlooking the countryside, this
small village (or rather castle) is a stunning little gem completely surrounded
by an intact city wall. With its many towers, it looks like it’s right out of a
postcard.
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San Gimignano, Italy
What do you think of when you hear “the medieval Manhattan”? Yep, it’s an old
town full of towers. What used to be over 70 towers, only 14 remain today. But
they still dominate the appearance of the town. While all Tuscan towns are
well-known for one or a few towers, 14 is quite a number. So I was curious and
researched a bit about why San Gimignano has so many more towers. And guess
what? Those towers used to be a symbol of power and wealth, so rich families
were competing about who can build the tallest tower. And with its prime
location along a Roman trading route, there were plenty of rich families, as you
can imagine. San Gimignano is small. But since it’s so pretty, it’s quite a
popular stop during a Tuscany road trip. So it can get quite crowded and you
better come in the morning or late afternoon to best enjoy the medieval town. To
do in San Gimignano: * Climb up Torre Grosso – A true highlight is the view
across the town and its surrounding landscape from this tower. * Take the effort
to queue at Gelateria Dondoli – to try the world-famous and awarded ice cream *
Vino – Try the Tuscan white wine Vernaccia di San Gimignano & stop by the
closeby Vineyard Teruzzi & Puthod.
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Florence, Italy