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Tuscany roadtrip – Most beautiful towns in Tuscany and wine tasting

Tuscany roadtrip - Leaning tower of Pisa

A Tuscany roadtrip is a must if you go to this part of Italy. There is so much beauty, in the region. From the famous cities like Florence, Siena and Pisa, but also smaller towns in Tuscany. Also a visit of Tuscany would not be complete without a wine tasting  as Tuscany is the producer of the well know Chianti wine.

Roadtrip in Tuscany, top towns in Tuscany not to miss !

Siena, Italy

Siena is a UNESCO World Heritage Site. It is such a beautiful city. You can do everything by walk. The Duomo cathedral and the piazza del Campo are the most important sights but wandering the narrow streets is very nice too. A very charming city that is not to miss.

If you go to Siena, my tip is to have dinner at Antica Osteria da Divo. Their specialities are truffle but you can also find other speciality from Tuscany!

Pisa and it’s famous Piazza dei Miracoli

Suggested by Greta from Greta’s travel

If you’re planning a trip to Tuscany, you can’t miss Piazza dei Miracoli in Pisa. Piazza dei Miracoli, previously known as the Piazza del Duomo, is home to the famous Leaning Tower of Pisa, but also the baptistry and cathedral of Pisa. For such a small area (9 hectares) it holds one of the finest architectural complexes in the world and is recognised as an important centre of Medieval art.

Access to the Piazza is free, however if you want to access any of the three buildings you will have to purchase a ticket. If you want to climb the Leaning Tower or Pisa make sure to get there early in the morning, or purchase in advance a skip-the-line ticket since the queue can get pretty big. From the top you will be able to get a stunning view over Piazza dei Miracoli and the rooftops of Pisa.

If you don’t want to go inside the baptistery, cathedral or tower you can just enjoy the atmosphere and beauty of the square. The buildings are architectural beauties even from the outside, with intricate carvings and decorations on the walls and doors. There are also a number of cafes and restaurants along the side of the square, where you can have a coffee or meal while enjoying the view. Don’t forget to take a photo while you pretend to hold up the Leaning Tower of Pisa, otherwise how else will your friends know you were in Tuscany?

Tuscany roadtrip The Leaning tower of Pisa and Duomo in the back

Marina di Pisa beach – a famous beach town in Tuscani near Pisa

Suggested by Jaclyn from Your travel spark

If you are in the Tuscany region, and specifically Pisa, you should take a few extra minutes and drive out to Marina di Pisa Beach. Only 14 km from Pisa, as well as the Leaning Tower, the beach takes only a few minutes to drive and is located within a quaint Italian village.

The beach is miles long, and there is plenty of parking. You can walk along the beach or climb the many rocks that jut out into the sea. However, if you’re looking for a nice place to lay out all day and get a tan, this beach may not be it. Although the bright white appearance appears to be sand, it is actually small pebbles, and is not the most comfortable sunning location. The green sea water and white stones make it a picturesque location for a photo shoot or just to sit and clear your head.

Try one of the many small restaurants, bars, and gelato restaurants close to the beach. The small town atmosphere and beautiful surroundings make it a perfect lunch location.

If you’re driving through the Tuscan region, Marina di Pisa can be a great day trip. It is within a few hours of many of the other cities on the Tuscan countryside. We took a day trip from Florence to Pisa, Marina di Pisa, Livorno, Volterra, Siena, and back to Florence – and it took only about 8 hours.

Florence – the most famous town in Tuscany

Suggested by Kaila from Nomlist

The grand capital of the Tuscany region is certainly a popular and delicious destination in Italy and should definitely be on your list of places to visit. Known as the cradle of the renaissance it has a plethora of beautiful buildings and sights, all circled around the lovely Arno river.

The city’s 600-year-old cathedral, Santa Maria del Fiore, or The Duomo, is a must-see. Its large domed roof towers over the fairly low skyline and is to this day the largest brick and mortar dome in the world. For the art lover, a visit to Uffizi Gallery is a must. Built in the 16th century, this exquisite building houses many masterpieces of the Renaissance.

When you need to cross the river Arno, be sure to do it via Ponte Vecchio at least once. This unique bridge is lined with souvenir and jewelry shops on each side, supported by pillars.

There are also many churches and chapels to visit in the city, so feel free to take your pick, but do consider Santa Croce. This Neo-Gothic church is a beautiful building, has amazing frescoes, and holds the tombs of both Michelangelo and Galileo.

Tuscany Roadtrip Florence

Roadtrip in Tuscany – Drive through the most beautiful villages in Tuscany

Lucca – A medieval town in Tuscany

Suggested by Katy from Untold Morsels

Tuscany is a region full of amazing cities and picturesque hill towns but our favorite place is pretty Lucca. This beautifully preserved medieval city has many treasures to explore within its city walls. There is a vibrant piazza built on the site of an ancient Roman amphithéâtre and several Romanesque churches with impressive art collections.

But it is the city walls built in the Renaissance era that define the city and it is here where you can have the most fun. Transformed into a park in the 18th century, the walls form a 4 kilometer long green belt around Lucca. You can hire bikes and ride along the ramparts or simply join the locals strolling with their gelato. Along the way you can see wonderful views of the city, surrounding countryside and Lucca’s famous Torre Guinigi (tower) with its tree topped roof.

Lucca was the birthplace of opera great Puccini and there are museums, statues and activities related to the composer throughout the city. Even if you are not a big fan of opera I highly recommend the evening recital at Chiesa dei Santi Giovanni e Reparata. It only goes for an hour and you are treated to some of Puccini’s most famous arias in a setting that inspired him.

After the recital it is time for dinner at one of Lucca’s many restaurants featuring local Tuscan cuisine. At Ristorante Buca di Sant’Antonio [Via della Cervia, 3 Lucca] you must try the porcini mushroom risotto accompanied by one of the fantastic local wines from the cellar.

Tuscany roadtrip - lucca-town tuscany

Volterra – A lovely hilltop town in Tuscany

Suggested by Daniela from Ipanema travels

Volterra is a lovely hilltop town in Tuscany that shall be included on your Italian itinerary. What makes Volterra so different from the rest of the Tuscan villages, that it is a must-see? The layers of history and especially the Etruscan heritage that can be found there. Do you want to learn about the once powerful European civilization covered in mystery that has completely disappeared? Volterra will help you dig into the past and find out who the Etruscans were and how they lived.

The Etruscans are considered to be the indigenous population of what now Tuscany is. Even the name of Tuscany comes from the name of the Etruscans (Etruscus – Tuscus). The Etruscans have lived there between 800 BC and 250 BC, when they were assimilated in the Roman Empire. Volterra was one of the 12 cities that formed the famous Etruscan League.

Today, what we have left from the Etruscans are mostly legends and numerous artefacts. In Volterra you can visit the Guarnacci Museum that has a stunning collection of funeral urns, ceramics, coins, votive statuettes and other objects. Etruscan heritage in Volterra, however, is not only limited to the museums. You can also visit the Etruscan Acropolis which is an archaeological site and gives an impression of what the architecture of the Etruscans was and how they lived.

The journey back in time in Volterra continues and the next stop is the Roman period. There’s a beautiful Roman theatre in Volterra dating back to the 1st century BC. And then you have the medieval walled town with its palaces, churches and towers. And this is where the time has stopped in this small town.

If you want to experience the authentic Tuscan charm and are fascinated by legends and past civilizations, Volterra should be on your Italian bucket list.

Tuscany Roadtrip Volterra-town in Tuscany-Italy

Pitigliano – A town in Tuscany full of history

Suggested by Mar from The crowded planet

I’ve been visiting Pitigliano ever since I was a little girl, and it’s truly my favourite place in Tuscany. It’s located in the southern part of the region, away from the coast, in the heart of the Etruscan homeland. The Etruscans were a population that existed in Tuscany until the Romans defeated them in the 5th century BC, and slowly Etruscan culture was lost. Pitigliano is a great place to learn about the Etruscans, with a museum and a network of ‘vie cave’ surrounding the city – these were paths dug by the Etruscan in the soft tufa stone of the hills around Pitigliano, and survive to this day. The town of Pitigliano is your quintessential Italian hilltop village, built at the top of a tufa rock, with stunning views all over. There are little backstreets, independent shops selling handmade toys, self-printed books and a variety of quirky souvenirs, and naturally lots of excellent restaurants. A peculiarity of Pitigliano is that it houses a small Jewish neighborhood, known as ‘La Piccola Gerusalemme’ (Little Jerusalem), where you can visit a synagogue, museum and ritual bath. In summer Pitigliano is very busy, so I think September/October is a much better time to visit. Don’t miss including Pitigliano in your itinerary if you’re going to Italy in autumn!

La Verna – an eastern town in Tuscany

Suggested by David from Delve into Europe

The eastern side of Tuscany is well off the beaten path, and very different from what most visitors see of the region. It’s a largely mountainous and forested area, with relatively few sights and visitors.

We found out about La Verna through a chance conversation with a relative of our Italian host. Afterwards, we took a look at the map in the car, and with many a winding road to negotiate, we set out.

The Sanctuary of La Verna is a small monastery in Arezzo province. In the early 13th century it was a small mountain-top hermitage. It then received a humble but very well-known visitor – the future St Francis of Assisi, patron saint of animals and Italy. During his last visit to La Verna he received the stigmata – the same wounds Jesus Christ had when he was crucified.

After this miracle the monastery grew substantially. The main basilica church wasn’t finished until 1509, almost 300 years after his last visit. There’s another smaller church on the site, and a processional route to the chapel where he received the stigmata.

La Verna has a stunning setting on a mountainside, with a large wooden cross overlooking the contours and hills of the Casentino Forest below. After the crowds of Assisi, this is a wonderfully quiet, spiritual place to stop and contemplate the world.

Tuscany roadtrip not to miss Laverna town in Tuscany

San Gimignano – A medieval town in Tuscany

Suggested by Dan from Honeymoon always
San Gimignano is located halfway between Florence and Siena. As you approach the city, you will notice the distinct and well preserved medieval towers rising out of the town.  The small town was a hub in medieval times with families that constructed their towers to symbolize their wealth and power and has been very well preserved.
Today the town is full of gift shops, a delicious gelato shop with a very animated owner who has been awarded the best gelato in the world. There are many great restaurants with typical Italian cuisine. It is a bit small and can get quite crowded on a busy day.  Go during the shoulder seasons if you can or go early in the morning or later in the afternoon when the tour buses leave.
What is more memorable than the city is actually the view of the surrounding valley. There are several spots where you can simply look out with a breathtaking unobstructed view of vineyards and rolling hills for miles. Outside the city walls, you will find several bed and breakfasts to stay in. For a unique experience, take a horseback ride through the vineyards and olive trees.
Tuscany Roadtrip San Gimignano

Greve in Chianti

Suggested by Warren from Sling Adventures

Greve in Chianti has a great local community and a laid-back atmosphere with superb wine and food in the heart of the rolling hills of Tuscany. Only 30 minutes south of Florence, Greve revolves around its signature Chianti wine. The Chianti Classico can be identified the world over by the black rooster emblem that appears on the neck and seal of the bottle. So important is this branding that many towns in the region eligible to produce this wine have appended Chianti to their names.
Apart from wine, food is a big part of the reason to visit. La Terrazza on the piazza is great for a light cured meat, cheese and olive platter or la Bottega del Moro Ristorante for more substantial fare including juicy strips of steak with uber ripe cherry tomato salad.

The communal town centre revolves around Piazza Giacomo Matteotti which holds a statue of local explorer Giovanni da Verrazzano the first European to set eyes on what is now New York City, the Verrazzano bridge now named in his honour. The square is central for many markets and the annual wine festival held in September.

A hike up the hill to the historic walled village of Montifiorelli is worth the effort. Stroll the narrow, cobbled alley ways with views over picture postcard Tuscany. Sample locally produced cheese, wine and olive oil from unassuming vendors set within sandstone storefronts such as Maurizio Brogioni Chianti. Simply put, a visit to Greve in Chianti will force you to slow down, enjoy life and relax.

Tuscany roadtrip town in Tuscany Greve in chianti-montifiorelli-window

Tuscany roadtrip – The Etruscan Coast Wine and Olive Road and it’s beach towns

suggested by Michele from Intentional travelers

Tuscany’s Etruscan Coast runs along the western side of Italy, between Livorno and Piombino. The area has the beautiful rolling hills, olive groves, world class vineyards, and charming villages that you likely associate with Tuscany. But on top of all that, it also boasts sunny, sandy beaches.

Northern Europeans flock here for the summer sun, and bicycle tours cycle through on a regular basis, but the area remains surprisingly uncrowded.

Not everyone knows that this area is also home to world class wineries like Sassicaia. From the town of Bolgheri heading toward Castagneto, a road lined with cypress trees has been declared a national monument and continues through olive groves and fertile vineyards. This Wine and Olive Road is the perfect place to do a few tastings and admire the scenery.

Whether you prefer easy bike rides to the beach or hopping from town to town, walking to the village gelato shop or tasting wines and olive oils, there’s something for every one in this beautiful Italian countryside.

Tuscany roadtrip town in Tuscany Castagneto-Etruscan-Coast

Tuscany roadtrip – A Drive Through the Val d’Orcia

Suggested by Dhara from Not about the miles

One of the most stunning aspects of Tuscany is its beautiful countryside. When you think of Tuscany, the first image that comes to mind is the picture postcard view of rolling hills with vineyards and olive trees, and rows of cypresses marching across the landscape.

To view Tuscan countryside at its picturesque best, take a drive through the Val d’ Orcia just south of Siena. Although it’s beautiful any time of the year, it is especially scenic in the spring and the fall. In the spring, the bright green hillsides and fields of poppies brighten the scene, and in the fall, post harvest, you can see the crete senesi, the trademark gray clays of Tuscany.

Montalcino and Montepulciano – Must see towns in Tuscani

There are many beautiful towns that you can visit in this part of Tuscany, including Pienza, the “ideal Renaissance town,” Montalcino and Montepulciano with their world famous wines, San Quirico d’Orcia, and Bagno Vignoni. Also worth visiting are some of the lovely Tuscan abbeys scattered about here. The Abbazia di Monte Oliveto Maggiore near Asciano and the Abbazia Sant’Antimo near Montalcino are expecially beautiful. And near Pienza, a stop at the tiny Cappella della Madonna di Vitaleta is an absolute must.

While in the Val d’ Orcia, don’t forget to taste the local pici pasta with the pecorino di Pienza and the famous wines of the region.

Monteriggioni

Suggested by Marta from learning escapes

If you are after the charm of a quintessential Tuscan town, complete with medieval walls and hilltop position, look no further than the gorgeous village of Monteriggioni.

Located in Val D’Orcia, one of the most scenic areas of Tuscany, Monteriggioni is a pleasant stop on the way between Florence and Siena, less than an hour away by car.

The village is tiny and develops inside the compact frame of imposing fortifications. You can visit it in a matter of hours but its small size hides an important historical and architectural fact: Monteriggioni is the most important walled castle in the area and one of the best preserved in the whole of Tuscany!

The first thing you notice when entering Monteriggioni are indeed its walls: they date back to the XIII century and are accessible by visitors via steep steps. A walk along them is a lovely introduction to the city and will rewards you with beautiful views over the surrounding countryside.

Inside their perimeter you find the village’s main square. Here you have the main church, Santa Maria Assunta, an ancient well and many restaurant terraces, offering al fresco dining and Tuscan platters.  From the square depart a couple of small pretty roads, where you can find more restaurants, local craft shops and the local museum.

If you can, it is worth visiting the city in September, at the time of the city’s medieval festivals. During this event, the streets of Monteriggioni fill up with actors in period costumes entertaining the public with live performances that recreate the atmosphere of what chaotic life in a castle used to be like. A fun even for all ages!

Tuscany Roadtrip Monteriggioni main square (1)

Must include in your Tuscany roadtrip

Wine tasting in Tuscany

Suggested by Kate from Our Escape clause who spent her honeymoon in Tuscany!

“Tuscany is synonymous with delicious wine and beautiful, rolling countryside–so what better way to enjoy Tuscany than to combine the two and go wine tasting at a country vineyard?

Tuscan wines are legendary, especially their reds–Chiantis, Chianti Classicos (a personal favorite of mine), and Super Tuscans are known across the world, and somehow they manage to taste even better with a view of golden light clinging to grapevines and gently sloping hills.

Whether you book a group day trip from a tourism hotspot like Florence or Siena or you choose to drive out to the countryside yourself (with a designated driver in tow, of course–Tuscans aren’t exactly known for their light pours, and I’ve never left a wine tasting in Tuscany anything short of delightfully tipsy), wine tasting in the countryside is a must-do on any Tuscany itinerary.

Though you can go wine tasting in Tuscany at any time of year (and you should plan a trip out regardless of when you visit!), the best time to go wine tasting in Tuscany is in September.

September is the time of the grape harvest, so a September winery visit in Tuscany will mean not just delicious food and wine, but often a tour of the establishment and walk through the winery’s wine-making process–and since, many Tuscan wineries have been family-owned for generations, you’ll also be getting a peek at their family traditions!”

Tuscany Roadtrip Wine tasting

Tuscany roadtrip – End it with a beach holiday on Elba Island

If you have the chance, spend a few days on the beautiful island of Elba. Perfect to end up your roadtrip in Tuscany! You can read my tips for the perfect beach holidays on Elba island.

Truffle Hunting in San Miniato

Suggested by Daniela from A lovely planet

San Miniato is a sleepy town in the north of the region and one of the country’s most famous truffle spots. Truffles are notoriously difficult find and impossible to farm, so you won’t see them wandering around on your own. The best way to find them is to head out with a truffle hunter. Local Massimo comes from a family of truffle experts and he took us out with his trusty dog Mela. After an hours stroll we had two beautiful black truffles and headed back to Massimo’s family home to taste them, with some recipes prepared by his sister. Delicious! And a must do experience for food lovers visiting Tuscany.

Roadtrip in Tuscany, top towns in Tuscany - Truffles in Tuscany - Italy
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