Best Things to Do in Tuscany: Planning Your Perfect Trip

Scenic view of Tuscan Hills

Join Context Tours in Tuscany, hosted by a local expert

Known for its distinct blend of stunning landscapes, rich culture, and culinary mastery, Tuscany embodies the Italian culture of “la dolce vita” – the sweet life. Away from the hustle and bustle of Italy’s busiest cities, Tuscany is the perfect place to revel in the countryside and indulge in some of the best food and wine in the world.

Nestled within Tuscany’s rolling landscapes you’ll find beautiful cities that offer a unique look into the past, as well as a glimpse of Italy’s future. If you’re planning a trip to this incredible region, here are some places you can visit along the way.


Local legend says that Senius and Aschius, the sons of Remus and nephews of Romulus, founded Siena, and that story is told through pieces of art found throughout the city. While it was originally an Etruscan settlement, the colony disappeared and eventually grew under the rule of the Lombard kings. An economic and territorial rivalry emerged between Siena and Florence in the 13th century, with Florence ultimately claiming its place as the financial hub of Italy.

Siena and its people navigated centuries of challenges, from the Black Death to internal power struggles. In 1861, after centuries of strife and leadership transitions, Siena was absorbed into the Kingdom of Italy. The architecture and original character of Siena remain mostly untouched, and it feels like a window into medieval times.

Piazza del Campo

The Piazza del Campo (sometimes just referred to as the “Campo”) is the main public gathering space in Siena, and it is famed for its clamshell shape and extraordinary architecture. It lies at the intersection of three hills and is widely considered one of the greatest Medieval squares in Europe.

Palazzo Pubblico

Palazzo Pubblico is the central point of civic life in Siena. Praised for its harmonious integration with its surroundings, the interior is just as vibrant. With frescoes in nearly every room, this is a wonderland for art and history lovers.

Siena Cathedral

The majestic Siena Cathedral, a great example of Romanesque and Gothic architecture, is a true masterpiece. Visitors can experience classic works of art by Pisano, Michelangelo, Donatello, and more.

Guided Tour of Siena

Experience the magic of Siena on a small group, guided tour with a local expert. During a three-hour tour, you’ll bask in Siena’s superb artistic heritage, from its Medieval significance to its modern-day preservation. Stops on the tour include Il Campo, Siena Duomo, Palazzo Piccolomini, Palazzo Pubblico, and Via Francigena.


Because Carmignano includes everything Tuscany is famous for, it is sometimes referred to as a “mini-Tuscany.” Tucked within the hills of Montalbano, Carmignano offers incredible architecture, art, food, and wine.

Wine and Carmignano are inextricably linked – evidence of the city’s wine culture can be found throughout history. Historians believe that wine production has taken place in Carmignano for more than 1,200 years, and Julius Caesar even honored the city with a prestigious wine award. Carmpignano DOCG, the city’s flagship wine, is a national treasure. Produced in the verdant hills of Carmignano and Poggio a Caiano, this centuries-old tradition is a major draw for wine lovers visiting Italy.

Villa Medicea di Ferdinando

Dreamt up by the Grand Duke Ferdinando I de 'Medici, this architectural jewel was constructed by famed Florentine architect Bernardo Buontalenti from 1596 to 1600. After its construction, the property was essentially abandoned until Cosimo III undertook restoration efforts to reclaim its original magnificence. The exterior brings to mind the image of a fortress, but the interior features beautiful frescoes and a fireplace in every room.

Church of San Michele Arcangelo

St. Michael is the patron saint of Carmigano, and this church was built in his name in the 1330s. Embodying the classic Franciscan church style, the building eschews the typical grandeur of other architectural styles, like Roman and Gothic, and favors a simple external appearance. Though it was damaged during WWII, the church has undergone many renovations to preserve this beautiful relic.

Carmignano Wine Trail

There’s no better way to experience Carmigano than through its food and wine – and the Carmignano Wine and Prato Taste Trail allows you to do just that. Sip the region’s finest DOC and DOCG wines and olive oil, and sample the region’s famous cantucci (biscuits), salami, honey, vegetables, and more. The feast goes on and on!

Carmignano Private Wine Tour

If you’re looking for a chance to explore Carmignano’s unspoiled beauty, take our Carmignano Half-Day Wine Excursion from Florence. Located just a quick drive from Florence, you’ll visit famous spots like the San Michele and San Francesco church and Pontormo’s Visitation before an exclusive trip to a private estate. Get undiluted access to prized ancient cellars and taste Carmignano’s unparalleled wine, cheese, olive oil, and cold cuts.

Val d’Orcia

Tuscany’s iconic cypress trees line the roads and hills of this extraordinary city. Featured in countless famous movies, like “Gladiator,” “The English Patient,” and – of course – “Under the Tuscan Sun,” Val d’Orcia is the embodiment of quintessential Tuscany.

A constellation of small medieval villages punctuates the hills of Val d’Orcia, and it has been designated a UNESCO heritage site. This charming city has no shortage of Medieval architecture, breathtaking views, and gorgeous terraces.

Abbey of Sant'Antimo

The Abbey of Sant’Antimo is a mystical 12th-century abbey. Surrounded by olive trees and wheat fields, the abbey is a storied and serene place. Many believe the abbey was founded by Charlemagne around 781 as an act of gratitude for the assistance provided to him and his men. Monks still live at the abbey today, and you can hear beautiful Georgian chants during mass.

The Town of Montalcino

Perched atop the lush Tuscan hillside, Montalcino invites visitors to experience incredible views, a gorgeous Medieval town center, and delicious food and wine. Renowned for its production of Rosso di Montalcino (Montalcino red) and Brunello di Montalcino, connoisseurs flock to Montalcino for a sip of these famous wines. But wine isn’t the only attraction in this town – Montalcino’s Rocca, or fortress, is an impressive feat of architecture. Whether you meander through the town’s narrow alleyways or revel in the beauty of its piazza, Montalcino is a perfect complement to your Tuscany trip.

La Foce Garden

Expertly manicured lawns stretch throughout one of Italy’s most stunning private gardens. The gardens are a treasure trove, filled with box hedges, lemon trees, rose bushes, and lavender. Delight in the resplendent beauty of La Foce as you experience the rustic majesty of the Tuscan countryside alongside these cultivated, verdant gardens.

Take a Guided Tour of Val d’Orcia

Enhance your trip to Val d’Orcia when you take a private car with a local expert in history, art, and culture for a full-day tour on Context’s Full Day in Val d’Orcia Tour. Covering both the artistic and gastronomic highlights of the area, you’ll tour Medieval and Renaissance hill towns and a Brunello di Montalcino winery and taste locally produced cheeses, all while enjoying spectacular panoramas along the way.

More Tuscan Villages to Visit

Photo: Photo by Siegfried Poepperl from Pexels:

Enhance your trip to the Tuscan countryside with a visit to more villages. For the geographically inclined, check out this Tuscany Italy Map to visualize your adventure through Italy’s seemingly endless hills.

Popular villages include Montepulciano, San Gimignano, and Cortona. Many of these towns feature local markets, celebrations, and festivals that will be an unforgettable addition to your trip.

Outdoor Activities in Tuscany

Experience the natural beauty of Tuscany through its wonderful outdoor activities like hiking, biking, and horseback riding. There’s no better way to see the countryside than to immerse yourself in it! Whether you prefer an outdoor wine tasting or a rigorous day of cycling, there’s something for everyone in Tuscany.

Ready to up the ante on your Italian vacation? Go truffle hunting or enjoy an olive oil tasting tour. Truffle hunts are often led by specialized truffle dogs trained to seek out the world-famous fungus.

Tuscan Archipelago National Park

Take in awe-inspiring views of the crystal blue ocean at the Tuscan Archipelago National Park. Explore the seven islands included in the park (Elba island, Giglio island, Giannutri island, Capraia island, Pianosa island, Montecristo island, Gorgona island), on foot, horseback, or by bike as you traverse this biodiverse haven. Watch as sea birds take flight overhead or try to catch sight of the seahorses swimming below.

Apuan Alps

Apuan Alps Regional Park offers marble mountains starkly contrasted against green valleys and cerulean lakes. Wolves and golden eagles roam this incredible landscape, and the alpine garden includes a look at many rare plants. There are also over 1,300 surveyed caves located in the park.

Tuscan Cuisine

It’s undeniable – one of the best things to do in Tuscany is eat.

Indulge in Tuscany’s culinary culture, and you won’t be disappointed. Tuscan food is famous for its simplicity, fresh ingredients, and rich flavors. Whether you savor the local produce, wines, meats, and cheeses at an upscale restaurant or on a picnic blanket, Tuscan food is integral to its identity.

Some of the most famous Tuscan dishes include:

  • Ribollita – a hearty soup typically comprised of bread, beans, and vegetables (and sometimes meat)
  • Cantucci – crunchy, sweet almond biscuits usually served with dessert wine
  • Panzanella – a simple (but flavorful) salad with bread, onions, tomatoes, and basil, dressed with vinegar and olive oil
  • Pecorino – a sharp, tangy sheep's milk cheese

Sampling Tuscan food is a must-do when visiting, find a local trattoria or visit a market and sample some of the region’s freshest fare.

Plan a Trip to Tuscany

A visit to Tuscany is more than an excursion, it is an immersion in the history, traditions, and culture of Italy. Taste the famed wines, indulge in incredible food, and deepen your knowledge of some of the most beautiful historical sites in Italy.

We offer a wealth of guided tour options in Tuscany, from wine-tasting to walking tours, all created with your enjoyment in mind. Led by a local expert, our tours are one of the best ways to experience Tuscany and return home with a newfound appreciation for the region.

Your experience doesn’t just start when you get on the plane – Context Learning is a fantastic way to get a taste of Italy from the comfort of your own home.

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