Top Siena Private and Luxury - page 2

Explore some of the most popular Tuscan hill towns on this day trip to Siena, San Gimignano, and Monteriggioni from Florence. Enjoy visiting each town independently while also having the round-trip transportation organized in advance. Learn about the famous region from the tour leader on board the bus, listening to informative commentary as you travel.

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace: Piazza del Campo, the Duomo, Basilica di San Domenico and much more! You'll get to know the stories and curiosities of Siena! But also you will discover everything about local foods, Italian aperitivo in authentic local restaurants, and much more! What are you waiting for?

Avoid the hassle of organizing transport and winery visits in Tuscany on your own. This small-group experience simplifies a day in Chianti, combining scenic travel with curated tastings at local wineries and time to explore Monteriggioni’s medieval charm. Enjoy a relaxed, well-paced outing that lets you focus on the region’s flavors and landscapes rather than the logistics.

With no train station and spotty bus service, San Gimignano can be a hassle to reach from Siena. On this small-group tour, sip world-class wine and watch the sunset over Chianti and San Gimignano with stress-free transportation. 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.

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 2 historic wine cellars in Montalcino and vineyards, have lunch in Montalcino a winery in the hill town of Montalcino itself.

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

Stroll the charming Medieval streets of a Tuscan hill town with this 2-hour private tour of Siena. Learn about Siena's hidden gems from a knowledgeable guide in between visits to its most popular sights.

Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and Taste’ will introduce you to the local food and wine and to the fascinating world of sustainable wines. A journey through the secrets of viticulture in the age of climate change. Designed for all those who love fine wine and food, this intimate experience is for a maximum of 8 people and is led by one of the winery's owners. The winery tour will be followed by a guided sensory tasting session to capture and break down the different organoleptic profiles that participate in the complexity of our vintage and private reserve wines. Finally, you will enjoy a full lunch with the right food and wine pairings that will delight your palate and nourish your soul.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Savor the flavors of Siena on this delightful food tour, where you’ll explore the culinary treasures of Tuscany. A local guide will lead you through the charming streets, sharing fascinating insights about the region’s food and wine culture. Enjoy tastings of sparkling wine, red wine, gelato, pecorino cheese, cured meats, pizza and traditional sweets like cantucci and panforte. This small group experience ensures an intimate atmosphere, perfect for food lovers looking to immerse themselves in authentic Tuscan cuisine. - 2 - hour walking food tour through Siena’s enchanting streets - Taste a variety of local Tuscan products - Learn about the history and culture of Siena’s culinary scene - Enjoy a small group setting for personalized attention from your guide

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Please note that from November to April, and in case of bad weather, lunch will take place indoors. For tours departing on Mondays, lunch is always served in an indoor restaurant. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

Take a tour of Siena with a local, and get the lowdown on the city that the guidebooks can’t give. In a small group, explore Siena by foot to discover the history behind the UNESCO-listed Piazza del Campo, the oldest bank in the world, and other monuments. You also have a chance to sample classic food and drinks from Tuscany such as Pecorino cheese, homemade pasta known as pici, the famous Chianti wine, and more.

Avoid the challenge of navigating Tuscany’s rural roads and finding hidden countryside trails on your own with a guided horseback ride from Siena. This gentle journey carries you through rolling hills, vineyards, and olive groves, reaching quiet landscapes that cars can’t access. Ride at a relaxed pace while taking in the region’s natural beauty and rural charm without any planning or navigation stress.

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history, art and architecture of this wonderful medieval town,away from the crowded tourist routes. Uncover hidden squares, medieval alleys, 14° century perfectly preserved palaces, courtyards and ancient fountains with bewitching legends Enjoy the breathtaking views of Siena, perfect for unforgettable photos and peaceful and suggestive corners. Learn the stories about ancient noble families, medieval pilgrims and ancient disappeared monasteries Explore the territory of a Contrada to know the history of Palio race and visit, if you like, its private museum that I can book for you( tickets not included).

Avoid the stress of navigating winding country roads or unfamiliar public transit on your own and instead discover the fine wines and rich historical heritage of Chianti on this full-day trip from Siena. Travel through the Tuscan countryside to Castello di Brolio in the heart of the Chianti wine country for guided tasting sessions and a traditional Italian lunch. Enjoy the intimate atmosphere of a small group capped at only eight people.

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 a few 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.

Spend a memorable day exploring Tuscany’s most famous landmarks and landscapes on a relaxed and well-balanced itinerary from Siena. Your journey begins with a comfortable transfer by air-conditioned coach through the rolling hills of the Tuscan countryside. Reach Pisa, where you will have free time to explore the stunning Piazza dei Miracoli, a UNESCO World Heritage Site. Admire the world-famous Leaning Tower, the Cathedral, and the Baptistery from the outside, and take your time capturing unforgettable photos. Continue your experience with a stop in the heart of Chianti, where you will enjoy a traditional Tuscan lunch paired with a guided wine tasting at a local winery. In the afternoon, arrive in San Gimignano, one of Tuscany’s best-preserved medieval towns. On the way back from Pisa, you’ll pass through Florence before returning to Siena. This allows for a smooth and well-organized route across Tuscany.

Spend your day through the picturesque Tuscan landscape on an original Vespa scooter, enjoying peaceful roads that wind through the rolling hills of Chianti. This unique experience allows you to immerse yourself fully in the sights, scents, and sounds of the Tuscan countryside. As you navigate the winding roads, take in panoramic views of vineyards, olive groves, and ancient farmhouses dotting the landscape. Midway through your excursion, make a stop at a renowned winery nestled in the heart of the Chianti region. Here, indulge in a delightful wine tasting experience, savoring the flavors of locally produced wines that have been crafted with passion and expertise. After replenishing your energy, discover hidden gems off the beaten path, uncovering the rich history and culture that define this beloved region.

Siena has one of the most intact medieval cityscapes in Italy, and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, the town hall, and the Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is a certificate professional that has lived and worked in Siena for many years and can give you a full immersion view on the traditions of the city. We will discover together the myths, legends, and secrets of this medieval town and we will have the occasion to see very iconic neighborhoods and street where normally locals spend their time with friends and family. You will try 3 different flavors of Artisan Gelato & Tuscan wines. At the end of the tour our guide if requested will give you some great recommendation like the best restaurants or any other activities to do in Siena.