Top Siena Luxury Car Tours in 2026

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Siena Scavenger Hunt & Highlights Self-Guided Walking Tour

The Best Way to Discover Siena: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a traditional Ricciarelli almond cookie in a local pastry shop or enjoy the medieval atmosphere of the Piazza del Campo and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package - Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Cultural Context: Read the history and legends of each site as you explore. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Pinacoteca Nazionale, Baptistery of St John, Palazzo Piccolomini, Loggia del Papa, Tower of Mangia, Pubblico Palace, Fonte Gaia, Santa Maria della Scala, Facciatone, and the Duomo di Siena.

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Siena Scavenger Hunt & Highlights Self-Guided Walking Tour

2 hoursFree Cancellation

Price varies by group size

Member Pricing

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.

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

9 hoursFree Cancellation

Member Pricing

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

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Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

Price varies by group size

Member Pricing

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

Member Pricing

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

Price varies by group size

Member Pricing

San Gimignano, Chianti, and Montalcino Day Trip from Siena

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.

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

Member Pricing

Exclusive Montalcino Wine Experience

7 hours 30 minutesFree Cancellation

Special Offer

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

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Siena: Val d’Orcia Wine Tour with Lunch & Brunello

10 to 11 hoursFree Cancellation

Member Pricing

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.

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Hot Air Balloon Flight Over Tuscany from Siena

3 hoursFree Cancellation

Price varies by group size

Member Pricing

Discover UNESCO-listed Siena through the eyes of a local on this custom-made Lokafy walking tour. Skip the typical guided tour and instead connect with a Siena local who will show you around their city like a friend and introduce you to the neighborhoods that they know and love. As you explore the city, gain an insight into Tuscan culture, cuisine, and everyday life; and receive recommendations on where to eat, drink, and shop.

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Siena Private Walking Tour with a Local

2 to 6 hoursFree Cancellation

Price varies by group size

Member Pricing

Chianti Wines and San Gimignano Tour from Florence (1 Winery)

Immerse yourself in a 5-hour wine tour from Florence that promises a journey packed with adventure, luxury, and wine. Departing from your accommodation in Florence, head straight towards San Gimignano, a stunning medieval town in the country that boasts views of vineyards, olive groves, and rolling hills. Once in town, you'll have an hour of free time to shop at local artisan shops or take pictures of the intricate architecture of this ancient town.

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Chianti Wines and San Gimignano Tour from Florence (1 Winery)

5 hoursFree Cancellation

Member Pricing

Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.

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San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SIENA

Price varies by group size

Member Pricing

Vintage Fiat 500 Tour: Lunch and 2 Wine tastings in the Chianti

7 hoursFree Cancellation

Member Pricing

Discover the timeless beauty of Tuscany on a full-day tour visiting the medieval towns of Siena, Monteriggioni, and San Gimignano with the option of adding a visit to a local winery in the heart of the Chianti. Experience the enchanting atmosphere as you travel through the Tuscan countryside, characterized by rolling hills, vineyards, and olive groves. Wander through ancient streets, admire stunning architecture, and soak in the authentic character of three iconic destinations at a leisurely pace. - Full-day exploration of Tuscany’s medieval towns: Siena, Monteriggioni, and San Gimignano - Relaxed pace allowing for in-depth discovery of each town - Scenic journey through picturesque landscapes filled with vineyards and olive groves. POSSIBILITY TO ADD A STOP AT A WINERY. - Experience Tuscany’s rich history and charming atmosphere firsthand

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Tuscany Day Tour Siena, Monteriggioni and San Gimignano

8 hoursFree Cancellation

Price varies by group size

Member Pricing

This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.

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Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

Price varies by group size

Member Pricing

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).

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Secret Siena Walking Tour

2 hoursFree Cancellation

Member Pricing

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

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Signature Brunello di Montalcino Wine Tour from Siena

5 hours 30 minutesFree Cancellation

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Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint Francis in Assisi's Basilica. Stop for lunch in an intimate, local restaurant/farmhouse, for a gourmet meal with a glass of Montefalco Red or Sagrantino ready at hand for a toast, and experience their local extra virgin olive oil production. After lunch delight in Deruta, where you will encounter extraordinary ceramics and have the chance to visit Ubaldo Grazia, the world's most ancient majolica factory

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Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Price varies by group size

Member Pricing

Small group Chianti Classico & Brunello wine region from Siena

5 hours 30 minutesFree Cancellation

Must-Dos in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

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Top Siena Luxury Car Tours in 2026

19 results

Must-Dos in Siena

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni

Siena Cathedral (Duomo di Siena)

Piazza del Campo

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni

Siena Cathedral (Duomo di Siena)

Piazza del Campo

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni