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Best Things To Do in Tuscany, Italy

Sipping local wines and dipping bread into just-pressed smooth olive oils is one of the main things to do in this Italian region. Luckily, there are numerous wineries where you can to do this, such as Ciacci Piccolomini d'Aragona in Montalcino and Castello del Trebbio in Florence. And speaking of Tuscan towns, there are a handful of little cities worth exploring — Siena and Lucca to name a couple. Lastly, if you want to get a funny photo, a trip to the little town of Pisa with its tilting torre is a must. 

How we rank Things to Do.

#1
Florence Free

#1 in Tuscany, Italy

Free

Firenze, Tuscany's capital city, is known for its Renaissance art and architecture. You can climb to the top of the Duomo, gaze at Botticellis at the Uffizi Gallery, tour the Galleria dell'Accademia and stroll through the Boboli Gardens for a taste of the 13th through 16th centuries.

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Neighborhood/Area Type
More than Full Day Time to Spend
Florence

Firenze, Tuscany's capital city, is known for its Renaissance art and architecture. You can climb to the top of the Duomo, gaze at Botticellis at the Uffizi Gallery, tour the Galleria dell'Accademia and stroll through the Boboli Gardens for a taste of the 13th through 16th centuries.

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#2
Siena Free

#2 in Tuscany, Italy

Free
Siena vies with Florence for the title of the most charming city in Tuscany. While Firenze is known for its Renaissance influence, Siena exemplifies the Gothic era, and you'll find that near-pristine Gothic architecture fills the city. One of Siena's main attractions is also a UNESCO World Heritage Site: The breathtaking Piazza del Campo is a city square that sits at the base of three majestic hills. While you're there, climb to the top of Torre del Mangia (a part of the Palazzo Pubblico) for an awe-inspiring view of Siena.
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Neighborhood/Area Type
More than Full Day Time to Spend
Siena
Siena vies with Florence for the title of the most charming city in Tuscany. While Firenze is known for its Renaissance influence, Siena exemplifies the Gothic era, and you'll find that near-pristine Gothic architecture fills the city. One of Siena's main attractions is also a UNESCO World Heritage Site: The breathtaking Piazza del Campo is a city square that sits at the base of three majestic hills. While you're there, climb to the top of Torre del Mangia (a part of the Palazzo Pubblico) for an awe-inspiring view of Siena.
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#3

#3 in Tuscany, Italy

Free
Cinque Terre is a group of cinque (five) villages — Monterosso, Vernazza, Manarola, Riomaggiore and Corniglia — strung along cliffs that overlook the Ligurian Sea. Since it became both a UNESCO World Heritage Site and national park in the past couple of decades, the area has been saved from the commercialism that pervades most European cities today.
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Beaches Type
More than Full Day Time to Spend
Cinque Terre
Cinque Terre is a group of cinque (five) villages — Monterosso, Vernazza, Manarola, Riomaggiore and Corniglia — strung along cliffs that overlook the Ligurian Sea. Since it became both a UNESCO World Heritage Site and national park in the past couple of decades, the area has been saved from the commercialism that pervades most European cities today.
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#4
Lucca Free

#4 in Tuscany, Italy

Free

Located in northwest Tuscany and less than 20 miles from Pisa, this town is famous for its 16th-century walls — recent travelers recommend riding a bike atop them to get the best views. Or consider climbing to the top of the Guinigi Tower where you can overlook the entire city. There's also a rendition of the Duomo, called the Cattedrale di San Martino.

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Neighborhood/Area Type
More than Full Day Time to Spend
Lucca

Located in northwest Tuscany and less than 20 miles from Pisa, this town is famous for its 16th-century walls — recent travelers recommend riding a bike atop them to get the best views. Or consider climbing to the top of the Guinigi Tower where you can overlook the entire city. There's also a rendition of the Duomo, called the Cattedrale di San Martino.

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#5

#5 in Tuscany, Italy

Sovestro in Poggio Winery is a farming estate filled with fields of grapes and olives. The estate produces wines like the Tribolo and Chianti, as well as its own extra virgin olive oil called Bagatto. Like many of the estate wineries, Sovestro in Poggio also contains overnight accommodations. Recent visitors are almost unanimous in their praise for this estate, saying the scenery was "breathtaking," the food was "delicious" and the wine was "perfect."

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Wineries/Breweries Type
2 hours to Half Day Time to Spend
Sovestro in Poggio Winery

Sovestro in Poggio Winery is a farming estate filled with fields of grapes and olives. The estate produces wines like the Tribolo and Chianti, as well as its own extra virgin olive oil called Bagatto. Like many of the estate wineries, Sovestro in Poggio also contains overnight accommodations. Recent visitors are almost unanimous in their praise for this estate, saying the scenery was "breathtaking," the food was "delicious" and the wine was "perfect."

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#6

#6 in Tuscany, Italy

Visitors to the Castello di Verrazzano say its mix of warm hospitality, scenic beauty and delicious wine that is absolutely divine. Dating back to the 14th century, the estate also produces olive oil, honey, grappa and balsamic vinegar. So if you want to bring back a few souvenirs, Castello di Verrazzano has you covered — just know that you can buy the same wines cheaper at the local grocery store.

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Wineries/Breweries Type
2 hours to Half Day Time to Spend
Castello di Verrazzano

Visitors to the Castello di Verrazzano say its mix of warm hospitality, scenic beauty and delicious wine that is absolutely divine. Dating back to the 14th century, the estate also produces olive oil, honey, grappa and balsamic vinegar. So if you want to bring back a few souvenirs, Castello di Verrazzano has you covered — just know that you can buy the same wines cheaper at the local grocery store.

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#7

#7 in Tuscany, Italy

Castello del Trebbio hosts everything from a winery to a restaurant (and cooking classes) to accommodations. It's hard to pin down just what visitors like most about the experience. Some say its the family-run winery with simply tasty wine and olive oil. Others say the 12th-century castle's ambiance is the coolest, while some find tasting different Chianti vintages and learning to make Italian pasta the most satisfying part about this estate winery.

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Wineries/Breweries Type
2 hours to Half Day Time to Spend
Castello del Trebbio

Castello del Trebbio hosts everything from a winery to a restaurant (and cooking classes) to accommodations. It's hard to pin down just what visitors like most about the experience. Some say its the family-run winery with simply tasty wine and olive oil. Others say the 12th-century castle's ambiance is the coolest, while some find tasting different Chianti vintages and learning to make Italian pasta the most satisfying part about this estate winery.

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#8

#8 in Tuscany, Italy

Ciacci Piccolomini d'Aragona produces wines, grappas and olive oils in a beautiful swath of southern Tuscany. The estate itself dates back to the 17th century, making it a great stop for historians as well as gourmands.

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Wineries/Breweries Type
2 hours to Half Day Time to Spend
Ciacci Piccolomini d'Aragona

Ciacci Piccolomini d'Aragona produces wines, grappas and olive oils in a beautiful swath of southern Tuscany. The estate itself dates back to the 17th century, making it a great stop for historians as well as gourmands.

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#9

#9 in Tuscany, Italy

Castello di Volpaia is much more than a winery — it's an entire village, and a 11th-century one at that. The former churches, homes and underground passages have been converted into wine cellars, bottling plants, tasting bars, olive presses and even an underground wineduct. Visitors can even do some hiking in the surrounding countryside; the Enoteca (or shop) sells hiking itineraries, some of which can take up to three hours to finish.

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Wineries/Breweries Type
2 hours to Half Day Time to Spend
Castello di Volpaia

Castello di Volpaia is much more than a winery — it's an entire village, and a 11th-century one at that. The former churches, homes and underground passages have been converted into wine cellars, bottling plants, tasting bars, olive presses and even an underground wineduct. Visitors can even do some hiking in the surrounding countryside; the Enoteca (or shop) sells hiking itineraries, some of which can take up to three hours to finish.

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#10

#10 in Tuscany, Italy

Oh, the Leaning Tower of Pisa — so touristy and yet so fun. Each day, hordes of visitors come to the small northwestern Tuscan town of Pisa to take pictures "propping up" its tower. Some do it with their entire bodyweight while others hold it with a finger. Even just watching other tourists take pictures is pretty entertaining. 

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Monuments and Memorials Type
Less than 1 hour Time to Spend
The Leaning Tower of Pisa

Oh, the Leaning Tower of Pisa — so touristy and yet so fun. Each day, hordes of visitors come to the small northwestern Tuscan town of Pisa to take pictures "propping up" its tower. Some do it with their entire bodyweight while others hold it with a finger. Even just watching other tourists take pictures is pretty entertaining. 

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