A trip to Tuscany is truly unforgettable, with its landscape of endless vineyards and hills dotted with medieval villages and castles. Explore the historical centers of Florence, Siena, and San Gimignano and taste the region's famed wine at picturesque vineyards, estates, and bars. Savor the views with unique experiences, like ballooning over Chianti or walking along an ancient pilgrim path. Enjoy sunset-filled dinners, delicious cuisines, and some of Italy's most important history, architecture, and art.

Getting Oriented

The brick city of Siena. 

Tuscany is set in Northern Italy between Rome and Bologna, a scenic stretch of land featuring coastal zones along the Ligurian Sea and the iconic inland hilly terrain. Florence is the region's capital and the birthplace of the Italian Renaissance, but you can also explore other historic towns and cities, such as Siena, San Gimignano, and Monteriggioni. Escape the crowds and enjoy unique experiences, like hiking ancient paths and hot-air ballooning over scenic Chianti at sunrise. Discover all that Tuscany has to offer and how to get off the beaten path

No trip to Tuscany is complete without exploring its wine and culinary scenes. Find the best food in Tuscany and taste the famed varietals, including Brunello di Montalcino, Montepulciano d'Abruzzo, and Chianti Classico. Savor the region's incredible scenery with hilltop castles and dinners, and simply enjoy the tranquility and fresh country air.

Food & Wine in Tuscany

Tuscany and its Chianti region draw crowds for its famed gastronomy and some of the world's most popular wines. Visit towns like Montalcino, San Gimignano, and Monteriggioni.

Brunello di Montalcino Wine Tour

Get to know the world-renowned Brunello di Montalcino wine.

Peruse the Tuscan countryside and taste the region’s famous Brunello wines in and near the charming medieval town of Montalcino. You'll pop into a few selected wineries to tour the grounds, visit the cellars, and try some of the area's standard and more complex varietals. Then enjoy some free time to explore the town and climb the walls of its iconic fortress, where soldiers of the Republic of Siena took their last stand to Florence and the Medici. Stop to visit the ancient Benedictine abbey of Sant'Antimo and a family-run winery to savor a traditional Tuscan meal paired with local wines. Read More 

Chianti Castles Wine Tour

Discover castles and wine in Chianti.

The Chianti wine region within Tuscany (set between Florence and Siena) is world-famous for its iconic landscape of verdant valleys, hilltop medieval towns, stunning castles, and endless rows of grapevines. Your first stop is under the walls of Castello di Brolio, where the renowned Chianti wine originated. The castle has its own winery to enjoy a tour and introductory tasting of the Black Rooster Chianti Classico wine. Other highlights include exploring some small villages, like Meleto, touring other vineyards, and savoring a traditional Tuscan lunch. Read More

Tuscany Sunset Tour & Dinner

Savor a traditional Tuscan dinner with superb views.

The Tuscan landscape is beautiful in every season and at any time of the day, but it particularly shows off at dusk and sunset. Chase the waning rays starting with a scenic drive through the Chianti region filled with oak forests, cypress trees, and neat rows of vineyards. Tour a winery and taste Chianti Classico wine and olive oil before heading to the medieval fortress town of Monteriggioni and San Gimignano, the "town of towers." As the sun starts to make its descent toward the horizon, head to an organic farm for a traditional Tuscan dinner overlooking the countryside. Read More

Exploring Tuscan Cities

Tuscany played an essential role in Italian history, especially in the Middle Ages. Nothing proves this better than the historical centers of Florence and Siena. 

Florence Highlights Walking Tour

Enjoy a walking tour of Florence, the birthplace of the Italian Renaissance. 

Discover the art and history of Florence on a walking tour, where a guide will lead you through the old city center in search of fascinating architecture, art, monuments, and historical tales. You can choose between two options, with the first being a Renaissance-themed walk stopping at the main sites and touring the Accademia Gallery with Michelangelo's famed David statue. The second option visits Santa Croce Church with its masterpieces by Donatello, Giotto, and Della Robbia and tours the Uffizi Galleries with paintings by Leonardo da Vinci and Raphael. Read More

Siena Walking Tour

Explore the charming city of Siena in the heart of Tuscany.

Discover the exceptionally picturesque core of Siena, a hub of medieval architecture, art, and history. The city reached its demographic and economic peak between the 8th and 9th centuries, with most of its monuments and art depicting this glorious era. Start in the main square, Piazza del Campo, where bricked buildings ooze its warm, “Burnt Siena" color. Follow a local guide through the twisting streets and to the top of its hill to visit the Cathedral. Inside, discover masterpieces by Michelangelo and Donatello. Read More

Scenic Tuscany

Enjoy the peaceful Tuscan countryside with a unique twist: take a hot air balloon ride over Chianti and hike a historic pilgrim path through the landscape. 

Ballooning Over Chianti

Relish the incredible scenery of Tuscany at dawn from a hot air balloon.

View Tuscany and the famed Chianti region from above in a hot air balloon at sunrise. Start early for the best views! You'll ascend into the air and enjoy the colorful scenes of the Chianti region as the first rays of sunlight crest over the horizon. Savor panoramic vistas of the Tuscan hills, villages, vineyards, wine estates, and forests. Once back on the ground, enjoy a delicious breakfast featuring champagne, prosecco, and local Tuscan produce. Read More

Hiking the Siena Pilgrim Path

The medieval walled city of Monteriggioni along the Siena Pilgrim Path.

Enjoy a unique experience in Tuscany as you walk along Via Francigena, a scenic and famous pilgrim trail, from Siena to Monteriggioni. This easy trek follows ancient paths used by pilgrims since 800 CE when walking to Rome was a lifetime goal. Along the way, enjoy the views of the Tuscan countryside and stop to visit one of the area's oldest churches, the Romanesque abbey of San Salvatore and Cirino. Continue to the hamlet of Monteriggioni, mentioned by Dante Alighieri in his "Divine Comedy." Read More

How to Craft the Perfect Italy Itinerary with Tuscany

The quaint streets of Tuscany.

You could plan an entire vacation just in Tuscany alone! If you choose to focus on the region solely, set aside at least one week to explore the countryside. Learn more about how many days to spend in Tuscany, and discover our other favorite cultural experiences in the region.

But if you want to go beyond Tuscany and Chianti, you can easily combine the two with almost any Italian itinerary. The most popular combos include Milan, Venice, the Lakes District, & Tuscany; Rome, Naples, Florence, & Tuscany; or Bologna, "Food Valley," Cinque Terre, & Tuscany. Whether you want a luxurious trip, a foodie excursion, or a vacation steeped in history, Tuscany is a must-see!

Past kimkim travelers have enjoyed the following trips that include experiences in Tuscany: