Top Siena Private and Luxury

Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket. 

Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.

Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.

Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide. 

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at three wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop. The tour starts and ends in the village of Castellina in Chianti.

Experience the Tuscan countryside from a perspective rare to visitors on a private Vespa tour with round–trip transport from your Siena hotel. In addition to navigating for you, your guide ensures the best views and stops for photo opportunities along the way. The day includes a Tuscan–style lunch and complimentary wine tasting with vineyard views.

Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.

Discover the sights and flavors of Tuscany by bike on a private 6-hour tour. Set along gentle roads and trails, the countryside excursion is the perfect way to immerse yourself in the region’s world-famous landscape. Pedal your way to a traditional family farm and wine cellar. There you enjoy a filling meal paired with four different wines. Sample honey and homemade olive oil with bruschettas, cold cuts, and more.

Maximize time in Siena with a guided walking tour through the medieval city streets. See local landmarks including Piazza del Campo and the Siena Cathedral while hearing stories about the city’s history and architecture from a local guide. Explore a local district, called a Contrada, and learn about Siena’s famous Palio horse races.

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury Mercedes vehicle with a private guide who shares the best of the region.

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

Sip world-class wine and watch the sunset on this day trip to Chianti and San Gimignano from Siena. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills. Group size is reserved for eight people to keep the experience as intimate as possible. 

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills.  Explore a local vinyard with your private guide and discover the wine making process. In addition to living out your Italian dreams of crushing grapes with your bare feet, you’ll also enjoy a wine tasting, along with a homemade lunch.

Capture your memories of Siena on camera during this private photo shoot in the heart of the city. Bookable for a group of up to five people, the experience is led by a professional photographer with knowledge of the best backdrops around the beautiful city of Siena. Bring any additional clothing, shoes, or accessories to make the most of your photo shoot. After the shoot, take home a collection of quality digital images to impress friends and family back home.

Oenophiles will appreciate this tour through Tuscany, which is known for its outstanding Chianti wine. Visit a working vineyard to learn about and sample Chianti Classico, Chianti Riserva and Super Tuscan wines. Take a break to explore a nearby Medieval village, then visit a second farmhouse-style winery to sample more wines and local olive oils.

See a ceramic artist at work and learn about this unique craft during a Ceramic Experience Visit in Siena. Go behind the scenes in a functioning workshop and catch a glimpse of the tools needed to create ceramics. A small group size ensures an intimate atmosphere.

Embark on a quest around Siena by solving clues to start a war between the famous Tolomei and Salimbeni families, all with the help of your smartphone. Unlock new stories as you discover on your own the Siena Dome, the historical center, Piazza del Campo, Palazzo Tolomei, and more. + Discover the second-oldest bank in the world + Uncover the secrets of the Palazzo Tolomei + Admire the beautiful fountain at Fonte Gaia + Take selfies in Piazza del Duomo Each riddle you solve will lead you from one place to another, giving you exact directions, so you won’t need a map, a GPS or a guide. When you solve it and guess the answer, the secret story of that place is unlocked. Start and stop whenever you want.

Admire the gorgeous landscapes of Tuscany from above on this 1-hour hot air balloon flight from Siena! This thrilling hot air balloon ride takes you up 2,000 feet (609 meters) over the rolling hills, classic Italian villas, imposing castles and sprawling vineyards and olive groves of the Tuscan countryside. Toast to this unforgettable experience with a glass of sparkling wine upon landing.

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.

Castiglione della Pescaia is a fortified village overlooking the sea, a balcony overlooking the Tyrrhenian Sea. From here you can enjoy a panorama of rare beauty, among the most "rich and sweet in the Maremma". The view ranges from the Uccellina mountains to the heights of Punta Ala, from the coast drawn between the intense green of the pine forest and the blue of the sea; below, in the plateau (ancient kingdom of Lago Prile), the marsh of the Diaccia Botrona stretches out, with the elegant and evocative Red House in the foreground, one of the most representative examples of civil engineering that recalls the impressive reclamation work desired and built under the Lorraine. The well-preserved village has exposed stone streets, ancient portals, niches and arcades that chase each other ... all enclosed by mighty turreted walls. Castiglione della Pescaia is one of the most efficient tourist resorts of the Tyrrhenian Sea and in its canal port cradled fishermen's boats and "habituès" boats.

Explore Chianti’s backroads and beautiful vistas while traveling in a vintage SUV. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste plenty of famous Chianti wine along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a gourmet picnic lunch at a scenic family estate.

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.

This tour is a chance to see the heart of Tuscany. We arrive in San Gimignano famous for the old towers. Walking in the main street we will go up to the central square where we can see the ancient Piazza della Cisterna and the Cathedral square. After we will drive to Siena. The town was built on five hills, the first place to visit is the San Domenico church, then we climb up to the main street of via Banchi di Sopra following the ancient way of the pilgrims, arriving at Campo square where the Palio horse race takes place twice a year.

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair, includes hotel pickup and drop-off, and finishes with a lunch of Tuscan dishes and wine.