Top Experiences in Siena

Unique things to do, curated by kimkim specialists
Siena, located in Tuscany, offers a range of activities that will immerse you in the city's rich history and delicious gastronomy. If you'd like to wander the medieval streets and visit Sienna's highlights, including the main square, Piazza del Campo, and the Siena Cathedral, you might enjoy something like this guided city walk. If you prefer a food-focused outing, check out an excursion similar to this tasting of Siena, where you can sample local wines, olive oil, Pecorino cheese, and truffles. You also have the option to escape the city and enjoy an experience like this dinner in the hills of Chianti that offers beautiful views of San Gimignano and a traditional Tuscan feast with wine pairings.
Restaurant outside
Tuscany Sunset Tour & Dinner
5.0
(3)
9 hours
·
Small group
Visit the hills of Chianti and take in the magic of San Gimignano, best appreciated when the tourists leave and the romantic afternoon light takes hold. In the evening, enjoy a traditional dinner at a local farm overlooking the towers and the soft rolling, vine-covered hills.Start with a scenic...
Siena Food Tour
5.0
(2)
2 hours
·
Small group
Discover the scenic and delicious town of Siena with a guided walking and tasting tour. Your local guide will introduce you to traditional Tuscan food culture and Siena's most typical bites. You’ll not only taste regional specialties, but you’ll also learn about Tuscany’s wealth of foods. Observe...
Old homes in Montepulciano
Val D’ Orcia Wine Tasting in Tuscany
5.0
(2)
9 hours
·
Private
Enjoy a wine-tasting tour in the Tuscan countryside, vising the picturesque hilltop town of Montalcino. You’ll also taste local Nobile wines in historical cellars in Montepulciano and savor a full farm-to-table lunch near Pienza.You’ll start by touring the cellars and tasting the wines at a...
Shopfront selling Brunello di Montalcino
Brunello di Montalcino Wine Tour in Tuscany
5.0
(1)
9 hours
·
Small group
Explore the Tuscan countryside and taste the region’s famous Brunello wines while touring the surroundings of quaint Montalcino. You’ll visit a selection of small-sized wineries that produce more complex and interesting varietals. Your first stop is at a boutique winery, where you can walk...
Interior of the 14th-century Duomo di Siena
Siena Walking Tour
5.0
(1)
3 hours
·
Private
Explore the historic core of medieval Siena on a walking tour. Your passionate and professional guide will lead you through the city and offer insight into its history and culture. Siena reached its demographic and economic peak between the 8th and 9th centuries, with most monuments and art...
A typical Tuscan vineyard in the Chianti region.
Val D’ Elsa Wine Tasting in Tuscany
5.0
(1)
8 hours
·
Private
Enjoy a wine-tasting tour in the Tuscan countryside, vising the picturesque hilltop town of San Gimignano and the Fortress of Monteriggioni. At the end of the day, you’ll tour vineyards and cellars, taste Chianti Classico varietals, and savor a fresh farm-to-table lunch with local Vernaccia...
Pisa & Lucca Day Trip
4.5
(2)
5.5 hours
·
Private
Explore two of Tuscany’s must-see cities: Lucca and Pisa. Stroll around the typical Italian streets of Lucca, take a picture with the leaning tower of Pisa, and deepen your knowledge of fine wines while sipping a glass of red Chianti. Your first stop is Lucca. This city isn’t just famous among...
Day Trip to Volterra in Tuscany
6 hours
·
Self guided
Explore the Tuscan countryside by venturing into the town of Volterra. Weave through scenic countryside and reach the hilltop town and its incredible views. This walled town has deep roots in Etruscan history, and to this day, visitors can still see parts of its protective walls and ancient...
Piazza del Campo preparing for the horse race
Explore Siena with Kids
4 hours
·
Self guided
Siena is an interesting and charming Tuscan city that kids love! Surrounded by the beautiful countryside, you’ll visit the main sites in a family-friendly way, including the Natural History Museum. Spend time at the best museums for kids, play at safe and relaxing parks, and enjoy the most...
Dome of Basilica di Santa Maria del Fiore
Discover Florence with Kids
3 hours
·
Self guided
Florence is a wonderful city to visit with kids! We’ve gathered all our best tips and tricks to help you entertain the entire family. You’ll visit the main sights, including the Duomo, plus the Uffizi Gallery and the Accademia Gallery in a kid-friendly way. Spend time at the best museums for...
Day Trip to the Villages of Chianti
Self guided
Chianti Valley is known for its food, wine, and historic architecture, and you’ll have plenty of opportunities to experience all three as you meander along the Chiantigiana road. Visit the charming villages of Castellina in Chianti and Greve in Chianti and a local family-run winery. The route...
Day Trip to San Gimignano & Monteriggioni in Tuscany
Self guided
Enjoy a day exploring the scenic countryside and picturesque villages north of Siena. Start with a leisurely walk around San Gimignano, a quintessentially Tuscan town comprised of medieval buildings perched atop one of the region’s iconic hills. Located in the Elsa Valley, San Gimignano is most...
The village of Pienza in the Val d'Orcia.
Explore Tuscany with Kids
5 hours
·
Self guided
Tuscany is vastly known for its vineyards and wineries, but it has so much more to offer. If you’re not fond of winery visits, you’ll still enjoy the castles, small towns, and villages as you drive through magnificent nature and countryside. The landscape is famous as a setting for many iconic...
Piena
Day Trip to the Villages of Tuscany
5 hours
·
Private
Enjoy a guided exploration of Italy’s famed Tuscan villages. You’ll choose two towns to visit amongst the following: San Gimignano, Montalcino, Pienza, and Montepulciano. San Gimignano: One of the best-preserved medieval towns in Italy, San Gimignano sits perched atop an iconic hill. Located in...
Afternoon Tasting Workshop at The Tuscan Wine School in Siena
2 hours
·
Small group
Explore the world-renowned wine of Tuscany with a tasting at the Tuscan Wine School. As you sip different varietals, such as Chianti Classico and Brunello di Montalcino, you’ll learn about Tuscany's most important, traditional wines in a fun and informative way. Discover the secrets behind the...
The perfect glass of Chianti
Chianti Wine Tasting & Farm Lunch
8 hours
·
Private
Absorb Chianti’s scenic countryside with a driving and winetasting tour. You’ll twist and turn along panoramic roads, tour wine cellars, learn about the history of growing Chianti grapes, and savor a traditional lunch of local products on a family farm. As you set off for Chianti, enjoy the...
Explore the Chianti Vineyards by Vespa
7.5 hours
·
Small group
Explore the famous vineyards of the Chianti region in true Italian style on a Vespa scooter! You’ll ride along peaceful roads through the scenic, Tuscan hills, admiring Chianti's landscapes, medieval villages, and hilltop castles. After zipping through the countryside, stop for a wine tasting and...
Balloon Ride, Lunch, & Car Tour in Tuscany
10 hours
·
Private
Enjoy a one-of-a-kind experience as you fly over the scenic Chianti countryside, taking in the magical colors of Tuscany at dawn. You'll start early in the morning and make your way to the launch field just outside of Siena. Watch the exciting process of inflating the balloon as you receive a...
Landscape in Chianti region, near Siena
Horse-Drawn Wagon Ride & Picnic in Chianti
3.5 hours
·
Private
Explore the Tuscan scenery at a peaceful, relaxed pace. Your guide will lead you through the picturesque and aromatic Chianti region on a horse-drawn wagon. You’ll end your tour with a fresh picnic lunch and panoramic views, enjoying a truly unique way to experience Tuscany.As you make your way...
Chianti Evening Tour & Wine Tasting
4 hours
·
Private
Explore the magic of the Chianti countryside and taste its famous wine varietals. As you zip through scenic Tuscany, with its rolling hills, tall cypress trees, and endless vineyards, you’ll stop to visit two of the best local wineries in the region. Sit back and relax as you make your way...
San Gimignano & Chianti E-Bike Tour
6 hours
·
Small group
Explore the culturally rich region of Tuscany with a guided e-bike and wine tour. You'll visit villages and historical sites such as San Gimignano and Staggia and pedal across vineyards and the Chianti Classico area fields. Cycle along bike paths and countryside lanes with no vehicular traffic,...
Hiking the Pilgrim Path from Siena to Monteriggioni
3 hours
·
Private
Hike along the scenic and famous Via Francigena pilgrim trail from Siena to Monteriggioni. This easy trek follows ancient paths used by pilgrims since the year 800 CE. People from across Europe followed the trail on their way to or from Rome when going on a pilgrimage was the goal of a lifetime....
Ballooning Over Chianti from Siena
4 hours
·
Small group
Enjoy the incredible scenery of the Tuscan countryside from a unique vantage point with a sunrise hot-air balloon ride. Starting early, you'll ascend into the air and enjoy the colorful views of the Chianti region as the first rays of sunlight crest over the horizon. Your journey above the...
Chianti Region
Chianti Castles Wine Tour in Tuscany
8 hours
·
Small group
Discover the world-famous wine region of Chianti, filled with tidy rows of vines, picturesque medieval villages, and stunning castles. Explore the hills between Siena and Florence, a landscape dotted with wineries and full of history. You’ll tour medieval castles, such as Brolio and Meleto, visit...
Day Trip from Florence: Tuscany Wine & Cheese Tour
8 hours
·
Private
Enjoy a tour through Tuscany’s delicious culinary staples and learn about its gastronomic traditions. You’ll savor Pecorino, the best-known and loved Tuscan cheese, plus homemade pasta, red wine, and extra virgin olive oil.Tuscany has always been a farming region. Its history and traditions...

Experiences in Siena, Italy

The Idyllic Landscape of Tuscany
Top Experiences in Tuscany

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.

Discover Italian History from Ancient Rome to the 20th Century
Top Historical Experiences in Italy

From Ancient Rome to the Middle Ages to the World Wars, Italy is steeped in fascinating history. Whether you're exploring historical Verona in the north, medieval Tuscany and the catacombs of Rome in central Italy, or the archeological ruins of Pompeii to the south, you can walk through the centuries. Discover the Colosseum and Roman Forum, stroll the cobbled streets of Siena, and discover the secrets of St. Mark's Basilica and Doge's Palace in Venice.

Learn more about Siena : Best of Siena
Top experiences in popular travel destinations in Italy: Rome · Venice · Amalfi Coast · Cinque Terre · Florence · Sorrento · Chianti · Lake Como · Milan · Montepulciano · Verona · Italian Riviera · San Gimignano · Naples · Bologna · Lake Garda
Top experiences in Italy