Private tours in Siena cut through the tourist crowds and get straight to the good stuff. The best ones combine historic walks through the medieval center with direct access to key sites like the spectacular Duomo cathedral. We especially love the combination history-and-food tours, where local guides connect you with authentic Tuscan flavors in family-run establishments while sharing stories of Siena’s rich past. Walking tours focusing on the city’s art treasures and quiet backstreets are particularly rewarding, especially when led by certified guides who know their stuff. The most worthwhile tours keep groups small and offer flexibility with timing. Let’s look at our favorite private tours in this remarkable Tuscan city.
Key Points
-
Siena’s private tours offer personalized experiences exploring the city’s historical landmarks and cultural heritage, with flexible scheduling and knowledgeable local guides.
-
Walking tours range from 2-3 hours, showcasing iconic sites like Piazza del Campo and Siena Cathedral, as well as hidden gems with personalized itineraries.
-
Culinary and wine tours provide immersive experiences, including private castle visits, multi-winery excursions, and traditional Tuscan lunches with expert sommelier guidance.
-
Full-day private tours combine Siena with nearby attractions like Pisa, San Gimignano, and the Chianti region, offering comprehensive Tuscan experiences.
-
Private art and history tours provide in-depth explorations of the Siena Cathedral, Civic Museum, and other significant landmarks, often with skip-the-line access.
Discover the Medieval Charm of Siena on a Private Walking Tour
Enjoy the medieval splendor of Siena on this private walking tour.
Explore the city’s charming old town, including the iconic Piazza del Campo, the Basilica of San Domenico, and the Sanctuary of St. Catherine of Siena.
An optional visit to the Siena Cathedral allows you to admire the stunning artworks by Michelangelo, Donatello, and Bernini.
Along the way, learn about the captivating Palio horse race and its deep-rooted traditions from your knowledgeable local guide.
This 2-3 hour tour is highly recommended, with 94% of 199 reviews praising the experience.
Customize your tour and add-on options such as the Contrada Museum to create a memorable journey through Siena’s medieval past.
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
Visitors can embark on an enchanting journey through the heart of Tuscany with a tour and wine tasting at a private castle near Siena. Priced from $45.44 per person, this 2-hour private group experience showcases the castle’s gardens, Renaissance chapel, and organic winery.
Guided by knowledgeable Elena, guests will learn about the castle’s history and wine cultivation while savoring organic wines. The tour also includes water, a snack, and private parking.
With an impressive 5/5 rating from 9 reviews, this experience is highly recommended for couples, friends, solo travelers, and families seeking a taste of authentic Tuscan charm.
Getting there is straightforward, with clear directions from the Siena highway.
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
The Private Tour: Secret Siena Walking Tour offers visitors a unique opportunity to explore the medieval charm of this remarkable Italian city.
With rave reviews and a 99% recommendation rate, this guided experience showcases Siena’s hidden gems, from winding streets to stunning churches. Priced at $268.11 per group, the tour allows you to create a personalized itinerary and discover local history and culture.
Led by knowledgeable guides, you’ll visit key sites like Piazza del Campo, Chiesa di Santa Maria in Provenzano, and Basilica di San Clemente without entrance fees.
The flexible pacing and accessible routes make this tour suitable for most fitness levels, ensuring an engaging and memorable exploration of Siena’s secrets.
Read our full review: Private Tour: Secret Siena Walking Tour Review
Book now: Check availability
Siena – Chianti – San Gimignano Private Tour From Florence
Setting out on a private full-day tour from Florence, guests have the opportunity to explore the historic city of Siena, traverse the picturesque Chianti region, and discover the medieval towers of San Gimignano.
This 8-10 hour tour accommodates up to 7 guests and is available in English, Italian, and Russian.
In Siena, visitors embark on a guided walking tour and enjoy free time for exploration and gelato.
The scenic journey through Chianti includes a tranquil lunch featuring Tuscan cuisine.
In San Gimignano, guests have free time to sightsee and indulge in local snacks.
This tour includes pickup, drop-off, museum tickets, and a wine tasting, with flexible scheduling and free cancellation available.
Read our full review: Siena – Chianti – San Gimignano Private Tour From Florence Review
Book now: Check availability
Afternoon Semi Private Chianti Tour From Siena
Although departing from Siena, this afternoon Chianti tour allows travelers to enjoy the picturesque landscapes and rich wine culture of the renowned Chianti region.
With a maximum of 6 participants, the VIP experience offers an intimate and personalized journey. Highlights include visiting a medieval castle and fortress in Montalcino, tasting four Chianti Classico wines paired with local delicacies, and exploring historical cellars to learn about wine production.
Travelers will appreciate the convenience of private transportation, the expertise of a licensed guide, and an included lunch.
At $213.42 per person, this highly-rated tour provides excellent value, earning a 97% traveler recommendation and an Excellence badge.
Read our full review: Afternoon Semi Private Chianti Tour From Siena Review
Book now: Check availability
Siena: Private Tour of the Treasure Chest of Tuscany
Immersing oneself in Siena’s captivating medieval allure is the essence of this private tour, which showcases the city’s revered status as the “Treasure Chest of Tuscany.”
Travelers commence their journey at the historical site of Monte dei Paschi di Siena, situated in the heart of Piazza Salimbeni, where a knowledgeable guide awaits to lead them through the city’s enchanting landmarks.
Over the course of two hours, guests will explore the renowned Piazza del Campo, admire the Gothic splendor of the Siena Cathedral, and capture the essence of the Facciatone, a photo-worthy viewpoint.
Along the way, they’ll explore Siena’s rich history, traditions, and local delicacies, creating a truly immersive experience in this Tuscan gem.
Read our full review: Siena: Private Tour of the Treasure Chest of Tuscany Review
Book now: Check availability
Pienza, Val Dorcia, Montalcino Wine and Pecorino Cheese PRIVATE TOUR From SIENA
From Siena, this private tour takes travelers on a captivating journey through the picturesque landscapes of Pienza, Val d’Orcia, and Montalcino.
Guests will explore these stunning regions, sample renowned Brunello di Montalcino wines and Pecorino cheese, and enjoy a delightful lunch at a local farm.
Traveling in a luxury Mercedes with a knowledgeable private guide, the tour includes hotel pickup and drop-off, WiFi, bottled water, and all entrance fees and gratuities.
With a minimum of 2 and maximum of 8 people, this tour has received 5-star reviews and 100% recommendation from previous travelers, who praise the guides’ expertise and the tour’s flexible, tailored itinerary.
Read our full review: Pienza, Val Dorcia, Montalcino Wine and Pecorino Cheese PRIVATE TOUR From SIENA Review
Book now: Check availability
Siena : Highlights Private Walking Tour
Explore the captivating history and architectural marvels of Siena with this 3-hour private walking tour. Priced from $95.11 per person, this wheelchair-accessible tour offers a customizable experience led by a knowledgeable local guide.
Explore the iconic Piazza del Campo, Siena Cathedral, and other notable sites like the Palazzo Pubblico and Basilica Cateriniana San Domenico. Enjoy the flexibility to tailor the tour based on your interests, and receive valuable advice on additional activities in the city.
With free cancellation up to 24 hours in advance and the option to reserve now and pay later, this Siena walking tour is a convenient and immersive way to discover the Renaissance treasures of this remarkable Italian destination.
Read our full review: Siena : Highlights Private Walking Tour Review
Book now: Check availability
Private Tuscany Tour to Siena and San Gimignano With Lunch
Embark on an enchanting day-long journey through the picturesque Tuscan countryside with this private tour to Siena and San Gimignano. Priced from $528.39 per person, this 10-hour excursion offers free cancellation and the option to reserve now and pay later.
Highlights include a walking tour of Siena, an authentic Tuscan lunch and wine tasting, and free time to explore the charming medieval town of San Gimignano.
Along the way, enjoy scenic views and cultural insights into the region’s history and heritage. With transportation in an air-conditioned minivan and a knowledgeable guide, this tour provides a well-rounded Tuscan experience, though it’s not suitable for those with mobility impairments.
Read our full review: Private Tuscany Tour to Siena and San Gimignano With Lunch Review
Book now: Check availability
Siena: Private Custom Tour With a Local Guide
For those seeking a personalized exploration of Siena’s rich history and captivating culture, the Private Custom Tour with a Local Guide offers an unparalleled experience.
Priced from $58.12 per person, this 2-8 hour walking tour can be customized based on individual interests. Guided by knowledgeable locals, visitors will discover the city’s main sights and hidden gems, learning about the significance of St. Catherine and the legendary Palio.
With pickup included and the option to reserve now and pay later, this tour provides flexibility and convenience.
Praised for their personalized insights and recommendations, the tour’s guides, such as Luca and Guisseppe, ensure an enriching and memorable exploration of Siena.
Read our full review: Siena: Private Custom Tour With a Local Guide Review
Book now: Check availability
Siena: Private City Highlights Walking Tour
Siena’s captivating history and architectural gems come alive on the Private City Highlights Walking Tour. Lasting 3 hours, this private guided experience showcases the best of the medieval city.
Guests will explore Piazza del Campo, the iconic Palio location, and gaze up at the towering 102-meter-high Torre Mangia. They’ll also discover the Gothic palaces and the renowned Fonte Gaia fountain.
An expert guide provides fascinating insights into Siena’s local traditions, including the contrade and the famous Palio horse race. With an English, Italian, or Spanish-speaking guide, this private tour offers a personalized and engaging way to uncover Siena’s rich history and culture.
Comfortable shoes are recommended, and hotel pickup/drop-off is included.
Read our full review: Siena: Private City Highlights Walking Tour Review
Book now: Check availability
Siena: 2-Hour Private Walking Tour
On this intimate 2-hour private walking tour, guests will discover the artistic, religious, and cultural treasures of Siena.
Priced at $274.76 for up to 20 participants, the tour includes a professional private guide and admission fees.
Highlights include visiting Piazza del Campo, the site of the famous Palio horse race, and the Duomo square with its marble striped cathedral.
Travelers will also wander through lesser-known medieval neighborhoods.
With English and Italian languages available, the tour has earned a perfect 5/5 customer rating based on 3 reviews, which praise the guide’s knowledge and the overall quality of the experience.
Guests can reserve their spot with no upfront payment and enjoy free cancellation up to 24 hours in advance.
Read our full review: Siena: 2-Hour Private Walking Tour Review
Book now: Check availability
Siena Private Walking Tour
Travelers seeking an immersive exploration of Siena’s storied past can embark on the Siena Private Walking Tour, a 1.5-hour journey that delves into the city’s Etruscan roots, Senones influence, and tumultuous Republic era.
Priced from $264.19 per group, the tour welcomes up to 15 participants and is led by a local professional guide.
Highlights include uncovering the impact of the Italian Wars and tracing Siena’s transition to Florence’s Duchy. Guests can admire the city’s medieval sculptures and architecture while gaining insights into its spiritual and earthly monuments.
With customizable options and an overall 5/5 rating based on customer reviews, this private walking tour offers a comprehensive and personalized exploration of Siena’s rich history and culture.
Read our full review: Siena Private Walking Tour Review
Book now: Check availability
From Rome: Tuscany Full-Day Private Group Wine Tasting Tour
Departing from Rome, this full-day private group tour whisks travelers to the renowned wine regions of Tuscany. Priced at €358 per person, the 9-hour tour offers wine tastings, lunch, and exploration of medieval towns.
The first stop is Siena for photo ops, shopping, and a coffee break. Next, visitors discover the UNESCO-listed San Gimignano, famed for its towers and wine.
The tour then visits a winery for tastings of 10 different wines and a lunch. Throughout the day, a knowledgeable guide and skilled driver provide transportation and assistance.
While reviews praise the overview of towns and enjoyable wine experience, some suggest more time in the towns and additional shopping opportunities.
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
Discovering Siena’s rich heritage and iconic landmarks comes to life on this 3-hour private walking tour.
Led by a local guide, you’ll explore the Basilica of San Domenico, Piazza del Campo, and the grand Palazzo Pubblico.
Marvel at the architecture and learn about Siena’s storied past.
Opt to visit the stunning Siena Cathedral, adorned with works by renowned Italian artists.
Throughout the tour, you’ll find ample opportunities for memorable photos at locations like the Banchi de Sopra.
With a private group, you’ll enjoy personalized attention and engaging insights into Sienese traditions and the famous Palio horse race.
This wheelchair-accessible tour offers flexibility, as you can cancel 24 hours in advance for a full refund.
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
Enjoy the grandeur of the Siena Cathedral (Duomo di Siena) on this captivating private guided tour.
Over 2 hours, you’ll explore one of Europe’s most beautiful cathedrals, a UNESCO World Heritage Site. Marvel at artworks by renowned masters like Donatello, Michelangelo, and Bernini.
Gain fascinating insights from your professional guide as you visit key interior features, including the Cappella del Voto, High Altar, and Piccolomini Library.
Skip the ticket line for direct access to the cathedral’s interior.
With a customer rating of 4.6/5, this tour offers an exceptional experience, though feedback suggests the value may not fully meet expectations for all.
Read our full review: Siena: Duomo Di Siena Private Guided Tour Review
Book now: Check availability
Siena: Civic Museum Private Tour
This private guided tour of Siena’s Civic Museum takes visitors on an enriching journey through the evolution of Sienese art, from the 14th to the 19th century.
Over the course of 2 hours, guests will explore the renowned frescoes by artists like Simone Martini and Ambrogio Lorenzetti.
They’ll also visit significant rooms, including the 19th-century frescoes, Medieval World Map Room, and the Peace Room featuring the Allegory of Good and Bad Government.
The tour offers skip-the-line entry, private guidance, and museum access for $145.31 per person.
Wheelchair-accessible, with free cancellation up to 24 hours in advance, this experience is suitable for various traveler types seeking an in-depth art and history immersion in Siena.
Read our full review: Siena: Civic Museum Private Tour Review
Book now: Check availability
Chianti: Private Tour & Wine Tasting at Castle-Wineries
Setting out on a private tour and wine tasting adventure through the Chianti region, travelers can explore the captivating castle-wineries that dot the Tuscan landscape.
Priced at €595.00 per person, this full-day experience includes visits to three renowned wineries, allowing guests to sample prestigious wines and enjoy a gourmet lunch.
Pickup from Florence and private transportation are provided, ensuring a seamless journey.
Expert sommeliers guide visitors through the nuances of Chianti Classico and other notable varietals, pairing them with local delicacies.
With free cancellation up to 24 hours in advance and the option to reserve now and pay later, this tour offers a flexible and immersive way to discover the essence of Chianti.
Read our full review: Chianti: Private Tour & Wine Tasting at Castle-Wineries Review
Book now: Check availability
Guided Siena Tour With Lunch in Winery – Private Experience
Travelers seeking a more intimate exploration of Siena can opt for the Guided Siena Tour With Lunch in Winery – Private Experience.
This 2.5-hour tour provides a skip-the-line entry to the Siena Cathedral and Piccolomini Library, allowing visitors to admire the stunning Gothic architecture and intricate marble work.
The tour then continues with a visit to a local winery, where guests can enjoy a delicious lunch and sample the region’s renowned Chianti wines.
With an optional audio guide available, this private experience offers a tailored and immersive way to discover Siena’s rich history and culinary delights, away from the crowds.
Read our full review: Guided Siena Tour With Lunch in Winery – Private Experience Review
Book now: Check availability
Private Tuscany Tour to Pisa, Siena, San Gimignano and Lunch
A private Tuscany tour to Pisa, Siena, and San Gimignano offers travelers a comprehensive exploration of some of the region’s most iconic destinations.
Priced from Kč 12,631 per person, this 11-hour excursion includes guided tours, a typical Tuscan lunch, and wine tasting.
Highlights include the medieval neighborhoods of Siena, the Chianti Hills, and the stunning Leaning Tower of Pisa.
The tour’s flexible itinerary and knowledgeable guides receive positive reviews, though the lunch may not meet the expectations of some guests.
Suitable for most travelers, this tour provides a well-rounded experience of Tuscany’s rich history and culture.
Read our full review: Private Tuscany Tour to Pisa, Siena, San Gimignano and Lunch Review
Book now: Check availability
The Sum Up
Siena offers a wealth of private tour options to explore its medieval charm. Visitors can choose from walking tours, wine tastings, museum visits, and day trips to nearby destinations like Chianti and San Gimignano. These private tours provide a personalized experience, allowing travelers to discover Siena’s hidden gems and enjoy the city’s rich history and stunning landscapes. Whether you’re interested in art, architecture, or local cuisine, there’s a private tour in Siena that’ll cater to your interests.