20 Best Private Drivers In Siena

Expert private drivers in Siena offer terrific ways to explore this stunning medieval city and its surroundings. We especially love the customizable walking tours combined with wine tastings at atmospheric Tuscan castles – a perfect blend of culture and local flavors. The Chianti region tours are particularly worthwhile, featuring comfortable air-conditioned transport and stops at hidden gems most travelers miss. For food lovers, the unique dining experiences in ancient Etruscan caves simply can’t be beat. Full-day excursions to charming towns like Pienza and Montalcino provide excellent value with their all-inclusive pricing and expert local insights. Let’s explore our favorite private driving tours in Siena.

Key Points

• Siena offers customizable private walking tours with insider access and accessibility features, starting at the Basilica Cateriniana San Domenico.
• Guided Tuscan wine tasting experiences at private castles provide high-quality organic wines and historical insights for around $45 per person.
• Exclusive culinary adventures include private dining in an Etruscan cave with full-course menus and wine pairings, priced from $293.95.
• Semi-private Chianti tours and full-day private tours to Siena, Chianti, and San Gimignano are available with luxury transportation and quality ratings.
• Private tours of Siena’s highlights, as well as customizable full-day tours to Pienza, Val d’Orcia, and Montalcino, offer flexible booking and free cancellation.

Discover the Medieval Charm of Siena on a Private Walking Tour

Enjoy the captivating medieval ambiance of Siena on a private walking tour led by a knowledgeable local guide.

The 2-3 hour tour offers a customizable itinerary to suit your group’s preferences, starting at the Basilica Cateriniana San Domenico and ending at the iconic Siena Cathedral.

Explore the city’s rich history and culture as your guide shares engaging narratives. Gain insider access to the Contrada Museum with a donation, and purchase a cathedral ticket on-site.

The tour is wheelchair accessible and stroller-friendly, with service animals allowed. Most travelers can participate, though the cathedral is closed Sunday mornings until 1 PM.

Secure your spot with a lowest price guarantee and the option to reserve now and pay later.

Read our full review: Discover the Medieval Charm of Siena on a Private Walking Tour Review
Book now: Check availability

Siena: Tour and Wine Tasting in a Tuscan Private Castle

Travelers can explore the captivating history and savor the finest organic wines at a Tuscan private castle on this guided tour. Priced from $45.14 per person, the 2-hour experience includes a tour of the castle gardens, Renaissance chapel, and organic winery, followed by a tasting of international varieties.

Guests will enjoy the tranquil atmosphere of Val di Merse and receive historical insights from the knowledgeable tour guide, Elena. With an overall 5/5 rating based on 9 reviews, this tour offers a charming and high-quality wine tasting experience.

Included amenities, such as water, snacks, and private parking, enhance the visit. Clear directions guide travelers to the castle’s tree-lined entrance.

Read our full review: Siena: Tour and Wine Tasting in a Tuscan Private Castle Review
Book now: Check availability

Private Tour: Secret Siena Walking Tour

Those seeking a captivating exploration of Siena’s hidden gems can embark on the Private Tour: Secret Siena Walking Tour.

Offering a flexible duration, typically in the morning or afternoon, this private tour takes travelers on a personalized journey through Siena’s architecture and cultural treasures.

Led by a knowledgeable local guide, the tour includes visits to notable sites like Piazza del Campo, Chiesa di Santa Maria in Provenzano, and Basilica di Santa Maria dei Servi, all with free admission.

Travelers can expect to discover the city’s alleys and streets, learn about the Palio di Siena and its 17 contrades, and enjoy unique photography opportunities with panoramic views.

With a 99% recommendation rate and 5.0 overall rating, this tour provides a customized and immersive experience in the historic city of Siena.

Read our full review: Private Tour: Secret Siena Walking Tour Review
Book now: Check availability

Siena – Private Dinner With Fine Wines in Etruscan Cave

Siena’s gastronomic allure extends beyond its historic streets, as evidenced by the exclusive Siena – Private Dinner With Fine Wines in Etruscan Cave experience.

This 2-hour private dining journey transports guests to an ancient Etruscan cave at Ristorante Casa Tua Siena. Priced from $293.95 per person, the experience offers a full-course menu with wine pairings, including Gota cotta di colle val dElsa, Pici al cacio e pepe, and Millefoglie.

The intimate setting features a warm ambiance of local materials, soft lighting, and aged wine bottles. While not suitable for all, this indulgent culinary adventure earns a 5/5 rating from guests seeking an unforgettable evening in Siena.

Read our full review: Siena – Private Dinner With Fine Wines in Etruscan Cave Review
Book now: Check availability

Afternoon Semi Private Chianti Tour From Siena

This afternoon semi-private Chianti tour from Siena offers travelers a VIP experience exploring the renowned wine region.

With a maximum of 6 people, the 3-hour tour includes private transport, a licensed guide, and a visit to a family-owned winery for wine tastings paired with local delicacies.

Guests can discover the history of Chianti, tour Montalcino’s medieval castle and fortress, and explore the historic wine cellars.

Highly rated at 4.9 out of 5 from 30 reviews, the tour emphasizes quality over quantity, allowing participants to savor the region’s finest Chianti Classico wines.

At €199 per person, the experience includes a tasty lunch and complimentary cancellation up to 24 hours in advance.

Read our full review: Afternoon Semi Private Chianti Tour From Siena Review
Book now: Check availability

Siena – Chianti – San Gimignano Private Tour From Florence

Set out on a private full-day tour that whisks you from Florence to the captivating destinations of Siena, the Chianti hills, and the medieval town of San Gimignano.

Priced at $398.94 per person, this 8-10 hour excursion includes a guided walking tour of Siena, a scenic drive through vineyards, and a Tuscan lunch experience.

Explore the Gothic architecture and medieval streets of Siena, then enjoy free time for shopping and sightseeing in San Gimignano.

Transportation is provided in an air-conditioned private car or van, and the tour is wheelchair accessible.

With water, museum tickets, and wine tasting included, this private tour offers a comprehensive and convenient way to discover Tuscany’s highlights.

Read our full review: Siena – Chianti – San Gimignano Private Tour From Florence Review
Book now: Check availability

Pienza, Val Dorcia, Montalcino Wine and Pecorino Cheese PRIVATE TOUR From SIENA

Exploring the picturesque Tuscan landscapes beyond Siena, this private full-day tour provides an immersive journey through the renowned wine and culinary regions of Pienza, Val d’Orcia, and Montalcino.

Guests will sample the world-famous Brunello di Montalcino wine, indulge in a lunch prepared by a local resident, and enjoy the flexibility of a customizable itinerary.

Traveling in a luxury Mercedes vehicle with a knowledgeable private guide, visitors will be treated to stunning views and authentic Tuscan experiences.

With all entrance fees, tastings, and gratuities included, this tour offers exceptional value for money and consistently high traveler satisfaction.

Read our full review: Pienza, Val Dorcia, Montalcino Wine and Pecorino Cheese PRIVATE TOUR From SIENA Review
Book now: Check availability

Siena: Private Tour of the Treasure Chest of Tuscany

Frequently regarded as the “Treasure Chest of Tuscany,” the historic city of Siena beckons visitors with its well-preserved medieval charm.

A private tour lasting 2 hours offers an immersive experience, starting at Piazza Salimbeni and showcasing the city’s main attractions, including the iconic Piazza del Campo, the Cathedral of Siena, and the Facciatone.

Guests can choose from live tour guides in multiple languages. Priced from $173.22 per person, the tour allows for flexible booking and free cancellation up to 24 hours in advance.

Highlights include exploring the Gothic-style cathedral, learning about the Palio horse race, and discovering Siena’s narrow streets, ancient palaces, and local delicacies.

Read our full review: Siena: Private Tour of the Treasure Chest of Tuscany Review
Book now: Check availability

Siena : Highlights Private Walking Tour

The private walking tour of Siena’s highlights provides visitors with an immersive exploration of the city’s rich history and architecture.

Starting at Viale Curtatone, the 3-hour tour takes guests through the iconic Piazza del Campo, the magnificent Palazzo Pubblico, the UNESCO-listed Palazzo Tolomei and Palazzo Salimbeni, the Basilica of San Domenico, and the renowned Siena Cathedral.

Accompanied by a knowledgeable local guide, the private experience offers insights into Siena’s culture and traditions.

Wheelchair accessibility, flexible booking, and a free cancellation policy up to 24 hours in advance make this tour an attractive option for those seeking a personalized discovery of this Tuscan gem.

Read our full review: Siena : Highlights Private Walking Tour Review
Book now: Check availability

Private Tuscany Tour to Siena and San Gimignano With Lunch

This private Tuscany tour offers an immersive exploration of two of the region’s most captivating destinations – Siena and San Gimignano.

Priced from $524.92 per person, the 10-hour excursion includes round-trip transport, an authentic Tuscan lunch, and wine tasting.

Visitors will enjoy 1.5 hours of sightseeing, shopping, and exploring in San Gimignano, followed by a guided tour of Siena’s historic landmarks, including the iconic Piazza del Campo and the Duomo.

The tour also provides opportunities to learn about the region’s rich cultural heritage, from the Palio horse race to the 17 contradas of Siena.

With free cancellation and flexible booking, this tour promises an unforgettable Tuscan experience.

Read our full review: Private Tuscany Tour to Siena and San Gimignano With Lunch Review
Book now: Check availability

Siena Private Tour: Discovering the Legendary Palio Spirit

Enjoy the legendary Palio spirit during this private tour of Siena.

Explore the city’s medieval alleys, discover the iconic Piazza del Campo, and visit the awe-inspiring Cathedral and Baptistery.

Your expert guide will bring Siena’s history to life, sharing insights into the influence of the Medici family and the renowned Palio horse race.

Capture panoramic views from the Palazzo Comunale and Torre del Mangia, and uncover the secrets of the Fonte Gaia, a prominent Sienese water source.

This 2-hour tour provides a comprehensive introduction to Siena’s architectural gems and cultural traditions, all at a cost of Kč 6,436 for a group of up to 25 participants.

Read our full review: Siena Private Tour: Discovering the Legendary Palio Spirit Review
Book now: Check availability

Siena: Private Custom Tour With a Local Guide

Why settle for a generic group tour when you can experience Siena through the eyes of a local guide? This private custom tour offers flexibility, personalization, and insider knowledge.

Prices start at $57.74 per person, with options for 2-8 hour tours in English, Italian, or Spanish. The tour includes hotel pickup and is wheelchair accessible.

Explore Siena’s main sights and hidden gems, with a guide providing insight into the local culture and customs. Reviewers praise the knowledgeable guides and customized experiences, like witnessing the renowned Palio horse race.

The tour includes guidance, but excludes tickets, food, and transportation beyond the walking tour. Booking is flexible, allowing for adjustments based on your travel plans.

Read our full review: Siena: Private Custom Tour With a Local Guide Review
Book now: Check availability

Siena: Private City Highlights Walking Tour

A private guided walking tour of Siena, a medieval city in Tuscany, provides an immersive exploration of the historic center, rich in history, art, and traditions.

Lasting 3 hours, this tour costs from €120.00 per person and is available in English, Italian, and Spanish. Guests can discover key sites like Piazza del Campo, Torre Mangia, and Fonte Gaia, as well as explore narrow streets and admire Gothic palaces.

The tour focuses on local traditions, particularly the contrade and the Palio di Siena. Starting and ending at Piazza S. Domenico, the guided portion lasts 2 hours.

While suitable for private groups, the tour isn’t recommended for those with mobility impairments.

Read our full review: Siena: Private City Highlights Walking Tour Review
Book now: Check availability

Private Hot Air Balloon, Pienza, Montalcino, Val Dorcia

Though soaring above Tuscany’s picturesque landscapes in a private hot air balloon may seem like a lofty experience, Balloon Team Italia offers just that.

Their exclusive tours in Pienza, Montalcino, and Val d’Orcia provide breathtaking views up to 6,000 feet for groups of two. For Kč 63,098, passengers enjoy a 1-hour flight, champagne toast, and local breakfast.

Weather-dependent take-offs are communicated in advance, and flights are insured and EASA-compliant. Sadly, pregnant women, young children, and those with certain restrictions can’t participate.

Nonetheless, this private adventure offers a unique way to experience the rolling hills, vineyards, lakes, and castles of Tuscany.

Read our full review: Private Hot Air Balloon, Pienza, Montalcino, Val Dorcia Review
Book now: Check availability

Siena: 2-Hour Private Walking Tour

For those seeking an immersive exploration of Siena’s captivating history and architecture, the 2-Hour Private Walking Tour offers an engaging experience.

Priced from Kč 6,562 for up to 20 participants, the tour delves into Siena’s artistic, religious, and cultural treasures. Highlights include visiting the Piazza del Campo, the Duomo square, and lesser-known medieval sights, all led by a professional private guide.

With the option to reserve now and pay later, and free cancellation up to 24 hours in advance, travelers can plan their visit with flexibility.

Reviews praise the tour’s informative and enjoyable nature, making it an excellent choice for those eager to discover Siena’s remarkable heritage.

Read our full review: Siena: 2-Hour Private Walking Tour Review
Book now: Check availability

Siena Private Walking Tour

Immersive in its exploration of Siena’s captivating history and architecture, the 1.5-hour Siena Private Walking Tour offers an engaging experience for travelers.

Priced from $262.46 per group of up to 15 participants, the tour uncovers Etruscan traces, Senones influence, the Republic era, and the impact of the Italian Wars.

Visitors can also witness Siena’s transition to Florence’s Duchy and admire the city’s 13th-century sculptures and medieval architecture.

Led by a local professional guide, the tour allows for customization and includes gratuities and entrance fees.

With an impressive 5/5 rating based on 3 reviews, this private walking tour promises insightful historical insights and immersive district visits.

Read our full review: Siena Private Walking Tour Review
Book now: Check availability

From Florence: Private Siena Day Trip With Transfers

Travelers seeking an immersive exploration of Siena can embark on a private day trip from Florence. Priced at €325.00 per person, the 5-hour excursion includes transportation via air-conditioned minivan and a 1-hour guided tour of Siena’s historic landmarks.

Guests can visit the iconic Siena Cathedral, admire the stunning Libreria Piccolomini, and explore the charming medieval streets. The tour is wheelchair accessible and offers the flexibility of free time for independent sightseeing.

With a live guide available in multiple languages and a free cancellation policy, this private day trip provides a personalized and convenient way to discover the beauty of Siena from Florence.

Read our full review: From Florence: Private Siena Day Trip With Transfers Review
Book now: Check availability

From Rome: Tuscany Full-Day Private Group Wine Tasting Tour

Departing from Rome, this full-day private group tour invites visitors to explore the picturesque Tuscan countryside. Priced at $375.84 per person, the 9-hour experience includes hotel pickup and drop-off, transportation by air-conditioned minivan, and a tour assistant throughout.

Highlights include a visit to the medieval town of Siena, where guests can taste local delicacies, and San Gimignano, a UNESCO World Heritage Site known for its “Hundred Towers.”

The tour also features a wine tasting of 10 different varieties at a local winery, followed by a lunch at the winery restaurant.

With options to cancel for a full refund up to 24 hours in advance, this tour offers a convenient way to discover the wonders of Tuscany.

Read our full review: From Rome: Tuscany Full-Day Private Group Wine Tasting Tour Review
Book now: Check availability

Siena: 3h Private City Walking Tour With Optional Cathedral

This 3-hour private walking tour offers an immersive exploration of Siena’s historic city center. Priced at €145 per person, the tour starts at the Basilica di San Domenico and covers iconic landmarks like Piazza del Campo, Palazzo Pubblico, and the Siena Cathedral.

Led by a live guide fluent in Italian and English, the tour provides skip-the-line access and opportunities for photo stops. While cathedral entry may be restricted on Sundays, the tour operates in all weather conditions.

With a 4.7/5 rating based on 388 reviews, the tour delivers exceptional value and a personalized experience, thanks to the knowledgeable and friendly guides.

Read our full review: Siena: 3h Private City Walking Tour With Optional Cathedral Review
Book now: Check availability

Siena: Duomo Di Siena Private Guided Tour

Immerse oneself in the grandeur of the Duomo di Siena, a UNESCO World Heritage Site, through a private guided tour.

The 2-hour experience whisks visitors past the ticket line for quick entry. A knowledgeable guide shares insights into the cathedral’s captivating artworks by renowned masters like Donatello, Michelangelo, and Bernini.

Key features include the Cappella del Voto, high altar, and intricately patterned marble floor. Visitors can also explore the Piccolomini Library and admire Michelangelo’s statues.

The tour is available in English and Italian, with headphones provided for larger groups.

While the tour’s value for money and organization receive mixed reviews, travelers consistently praise the guides’ expertise and entertainment.

Read our full review: Siena: Duomo Di Siena Private Guided Tour Review
Book now: Check availability

The Sum Up

Siena offers a range of private tour options for visitors to explore the city’s medieval charm. From walking tours and wine tastings to private dinner experiences, there are numerous ways to discover the history and culture of this Tuscan gem. Whether you’re interested in the Duomo, the city’s secrets, or the surrounding Chianti region, Siena’s private tour providers can tailor an unforgettable experience to suit your needs.