rovostays·

Luxury & private · Siena

Top 10 luxury & private things to do in Siena

Private cars, exclusive access, the kind of small group that doesn't share the experience with strangers. Premium tours through Siena for travellers whose calendar is the constraint, not the budget.

  1. Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour, Siena1

    1. Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

    5.0· 34 reviews· 8 hours

    Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive a tour of an organic dairy farm followed by a cheese tasting. Visit the beautiful Renaissance gem that is the hilltown of Pienza and enjoy lunch at your own leisure. Explore the hill town of Montalcino, and taste the rich flavours of the famous Brunello wine directly from a producer. Visit the farm, tour the cellars and learn more about this memorable nectar.

  2. Siena Street Food Tour With A Local Guide, Siena2

    2. Siena Street Food Tour With A Local Guide

    5.0· 6 reviews· 3 hours

    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.

  3. Siena Private Highlights and Hidden Gems Walking Tour, Siena3

    3. Siena Private Highlights and Hidden Gems Walking Tour

    5.0· 5 reviews

    This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist. After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.

  1. Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch, Siena4

    4. Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

    5.0· 1 reviews· 2 hours

    Off-road mini tour in a vintage Jeep through the landscapes of the vineyards. Taste Poggio ai Laghi premium wines, oils & vinegars. Enjoy the Tuscan Appetizers that enhance the flavors of each wine. Our wine expert will enhance this experience with Art & History.

  2. A Brunello Cooking Class with Vineyards View Winery, Siena5

    5. A Brunello Cooking Class with Vineyards View Winery

    5.0· 237 reviews· 4 hours

    Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance of our chef Alexandra, you will learn to make classic Tuscan dishes using the finest local delicacies, after which you will enjoy a private tour of the vineyards and the XV century castle that’s been in the family for 17 generations. Enjoy the lunch you prepared yourself on our panoramic terrace overlooking the rolling hills of Montalcino wine country. Each dish will be expertly paired with our own wine production. Tour Length: 4 hours ( Class + Lunch ) - Every day Departure Point:  Possible add-on we can organize for you PICK-UP DROP OFF IN THE PROVINCE OF SIENA Meeting time: 10.00 am Popularity: *****  (best seller wine and food tour in Tuscany) INCLUDED:  All Included  ( Cooking lesson, Tours, Tasting Lunch, Extra optional Transportation from and to the cooking venue )

  3. Siena Underground Wine tasting in a Medieval Cave, Siena6

    6. Siena Underground Wine tasting in a Medieval Cave

    5.0· 56 reviews· 1 hours

    For real wine lovers, This is a wine tasting experience hosted by a Sommelier. This tour offers you an exclusive wine tasting in a Medieval cave dating back to Etruscan period, 600 BC. This place is private and the only one accessible to public. Here you will have one of a kind experience tasting the best wines selection from Sienna's region. Brunello di Montalcino is also in the list of top 100 best wines in the world by the magazine Wine Spectator. Our Licensed Tour Guide will give you an introduction about Sienna history and assist you during the tour giving some tips on where to eat and what do in town during your stay. Please note: This experience being the a private premises is limited to 12 people per day.

  4. Private Tour: Secret Siena Walking Tour, Siena7

    7. Private Tour: Secret Siena Walking Tour

    5.0· 112 reviews· 3 hours

    Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter side of Siena.

  5. Tuscan Cooking Class in Central Siena, Siena8

    8. Tuscan Cooking Class in Central Siena

    4.8· 347 reviews· 4 hours

    Tuscan Cooking Class. Cooking Class of traditional Tuscan meal from starter to dessert including a fresh home-made pasta at the end of the lesson dinner with all prepared accompanied with Chianti Wine. The maximum number of customers per lesson 15 people. The school has applied all the legal regulations for sanitizing from Coronavirus. The school provides customers with everything necessary established by current safety standards (masks, gels, etc.). Customers actively participate in the preparation of recipes Use of seasonal and local ingredients Vegetarian and gluten-free menus available Customers will learn all the secrets of Italian and Tuscan cuisine and will receive handouts with the prepared recipes Private lessons on request in the morning

  6. Discover the Medieval Charm of Siena on a Private Walking Tour, Siena9

    9. Discover the Medieval Charm of Siena on a Private Walking Tour

    4.8· 257 reviews

    Decide with your guide if you want to have a 2 or 3 hours tour! Discover the treasures of one of the most beautiful cities in the world through the eyes of a local and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. Stroll in the ancient streets and admire the Basilica of San Domenico, the St. Catherine of Siena Church, Piazza del Campo, Palazzo Pubblico, ancient palaces, the important pilgrims road, the Baptistery and the Cathedral. If you wish, visit also the inside of the Cathedral, where you will admire the artworks of important Italian artists, such as Michelangelo, Donatello and Bernini. If you are more interested in the Palio tradition, we suggest to visit a Contrada Museum. You will find out why this horse race is so important for the Sienese and admire the prizes won over the centuries. Customize your tour with your guide!

  7. Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano, Siena10

    10. Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

    4.7· 3 reviews

    DEPARTURE GUARANTEED! Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine! Please note that from November to April I cannot guarantee the restaurant with view, as stated in the inclusions. The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters. There you will be surrounded by impressive views, art, culture, amazing wine and delicious food! Your semi private tour will be on board of a premium minivan with an English speaking driver, air conditioning and free water. WHY CHOOSE ME? Secure bookings, Guaranted Departures! 48 hours Cancellation policy, best rates guaranteed! Group of maximum 8 people.

Top places to visit in Siena

See all 20

More in Siena

Other things to do

Luxury & private in other destinations

Top luxury & private elsewhere

Same category, different cities — hand-picked luxury & private experiences across Italy.

See more

Places to see in other destinations

Hand-picked sights, neighbourhoods and landmarks across our destination network.

Visiting Siena?

Stay with Rovostays

Hand-picked, verified serviced apartments — concierge always included.