Tuscany, Italy Travel Guide

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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

Updated July 10, 2015

  • #1
    Things to do in Tuscany, Italy
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    #1 in Tuscany, Italy
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    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.

    But this city isn't just for art and architecture connoisseurs: There are quaint shops, delicious restaurants and decadent hotels. And with its red roofs, cobble stone streets and narrow alleys, it's also a very picturesque place to spend a few days. Be sure to hike to the top of the Piazza Michaelangelo, located across the Ponte Vecchio, for incredible city views and live music. Bring a bottle wine and watch the sunset — you won't want to miss it. For more information on this city, visit our Florence travel guide

  • #2
    Siena
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    Siena
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    #2 in Tuscany, Italy
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    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.

    As for museums, visitors find the Museale di Santa Maria della Scala and the Museo Archeologico are each worth a few hours of their time. And when it comes to churches, recent travelers recommend visiting several: the Siena Cathedral (or Il Duomo) for its beauty; the Cathedral of the Assunta for the surrounding landscape; and the Abbazia di Monte Oliveto Maggiore for its wine cellar. 

  • #3
    Lucca
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    Lucca
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    #3 in Tuscany, Italy
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    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.

    Luca is also praised for its native son Giacomo Puccini, who composed such operatic masterpieces as "Madame Butterfly" and "La Bohème," so art is aplenty. And art aficionados recommend popping into L.U.C.C.A. (Lucca Center of Contemporary Art) or strolling by the art show every third weekend of the month by the Piazzetta San Carlo to see local works of art. 

  • #4
    Cinque Terre
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    #4 in Tuscany, Italy
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    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.

    Visitors like to hike Cinque Terre's leafy crags; Via dell'Amour is a popular (and well-paved!) walk that connects Manarola with Riomaggiore. The trail with the best ocean views is from Vernazza to Monterosso. Unfortunately, this hike is also the most challenging and isn't for the faint of heart, as the trail (or lack thereof) is unpaved and involves lots of climbing under and over various terrain. To avoid the crowds and the heat, recent travelers recommend hiking in the morning. And if you're not up for hiking from town to town, you can always catch the train that runs along the coast and stops at each town. 

  • #5
    Sovestro in Poggio Winery
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    #5 in Tuscany, Italy
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    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."

    You'll find Sovestro in Poggio Winery in central Tuscany in the small town of San Gimignano. Although some recent travelers say the experience here is expensive, most say it's worth it. Reservations are mandatory for all visits. For more information, visit the estate's website

  • #6
    Ciacci Piccolomini d'Aragona
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    #6 in Tuscany, Italy
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    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.

    If you plan on visiting this winery, you'll want to be sure to take a guided tour. Recent visitors rave about the talented tour guides and their abundant amount of wine knowledge — you'll be a wine connoisseur by the time you leave. Tours give visitors access to all three of the wine cellars where you can learn how wine is produced. You'll find the winery in Montalcino on the hills flanking the Orcia River. For more information on this winery, visit its website

  • #7
    Castello del Trebbio
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    #7 in Tuscany, Italy
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    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.

    And here's an interesting historic tidbit: This castle was once owned by the Pazzi family, the arch enemies of another powerful Italian family, the Medicis. You'll find this winery on the outskirts of FlorenceWeddings are held here frequently, so be sure to call ahead for reservations. For more information, visit its website

  • #8
    Castello di Verrazzano
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    #8 in Tuscany, Italy
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    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.

    Many recommend booking the three-hour winery tour with lunch rather than just the winery tour itself, saying the food makes it worth the extra time and money. You'll learn how to properly pair and taste wine during the multicourse lunch. But if you're a vegetarian, recent travelers recommend skipping the lunch as the majority of the meal is different kinds of meats and not worth the extra cash. 

  • #9
    Castello di Volpaia
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    #9 in Tuscany, Italy
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    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.

    Guests rave about this estate nearby the breathtaking Radda di Chianti. You can also stay overnight in the castello's apartments or villas. You'll discover several delectable dining options around town and, of course, plenty of wine tastings. Various cooking and food classes are also offered, such as lessons on combining food and wine and how to serve Italian style. For more information on this winery, visit its website.

  • #10
    The Leaning Tower of Pisa
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    #10 in Tuscany, Italy
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    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. 

    At about 183 feet tall, the tower leans at about four degrees, meaning that at the top, it's displaced nearly 13 feet from its bottom. Yikes! And yet, it's still architecturally sound enough for visitors to walk up its nearly 300 steps to the top. And spying the exorbitant price of walking to the top (18 EUR), most travelers recommend snagging a few free pictures from the ground level. 

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