Siena’s best guided tours cut straight to the heart of this remarkable Tuscan city. For first-time visitors, the 3-hour private walking tours are your smartest bet, combining must-see stops at the striped-marble Duomo and the shell-shaped Piazza del Campo with insider stories you won’t find in guidebooks. Food enthusiasts should grab spots on the evening food walks – they’re intimate (max 8 people) and include generous tastings of Tuscan classics in family-run spots.
We especially love the early morning Duomo tours when you’ll have this architectural marvel nearly to yourself, and the sunset wine experiences in nearby Chianti vineyards are pure magic. The local guides are passionate experts who bring medieval Siena to life without overwhelming you with dates and details.
Let’s explore the specific tours that will make your Siena visit unforgettable.
Key Points
- Private guided tours of Siena Cathedral offer skip-the-line access and insights from local experts, priced at €137.50 per person.
- Food and wine tours provide a comprehensive exploration of Siena’s culinary heritage, visiting iconic landmarks and offering local delicacies and wine tastings.
- Guided walking tours, including the “Siena Like a Local” tour, offer personalized experiences with licensed guides and cover major sights in 2 hours.
- Guided bike tours in Val d’Orcia and Chianti Classico provide immersive 6-hour experiences, suitable for various fitness levels and offering lunch, refreshments, and insurance.
- Tours are highly rated, with positive feedback on knowledgeable guides, value for money, and engaging storytelling, catering to families and individuals with accessibility needs.
Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum
The Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum offers visitors an immersive exploration of the historic city. The tour departs from Piazza Salimbeni and concludes at the iconic Piazza del Duomo, allowing guests to experience the city’s most notable landmarks.
Groups are limited to a maximum of 20 travelers, ensuring a personalized experience. Throughout the tour, knowledgeable guides share insights into Siena’s rich history and culture, weaving in personal anecdotes to bring the city to life.
Highlights include the breathtaking Duomo and the charming Piazza del Campo, where visitors can admire the blend of architectural styles. For those seeking a local recommendation, the guides suggest trying the renowned Brunello wine.
Accessibility is a priority, with the tour being wheelchair and stroller friendly. However, visitors should note that the Duomo is closed on Sundays until 1:30 p.m.
COVID-19 safety protocols, such as mask-wearing and contact tracing, are also in place to ensure a safe and enjoyable experience.
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Siena: Food and Culture Guided Walking Tour
Exploring Siena’s rich food and cultural heritage, the Siena: Food and Culture Guided Walking Tour invites visitors on a captivating journey through the city’s historical streets.
Led by local experts, this 2-3 hour tour provides an immersive experience, taking guests to the city’s iconic landmarks, including the stunning Siena Cathedral and the charming Piazza del Campo.
Along the way, you will explore Siena’s renowned culinary traditions, sampling local delicacies and learning about the region’s acclaimed wine and olive oil production.
The tour also offers an in-depth look at the city’s art, architecture, and vibrant traditions, such as the famous Palio horse race.
With skip-the-line access to the cathedral, visitors can avoid lengthy queues and fully enjoy Siena’s captivating past.
Rated 4.9 out of 5 stars by 369 reviewers, this guided walk is an excellent choice for those seeking a comprehensive and enjoyable exploration of Siena’s cultural and gastronomic riches.
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Have You Ever Taken a Guided Tour of Siena?
Have you ever explored the captivating city of Siena through a guided tour? If not, now is your chance to experience the best that this historic Italian city has to offer. With a 100% recommendation rate and a Badge of Excellence, the guided tour of Siena is a must-do for any visitor.
The tour starts at the Basilica Cateriniana San Domenico and takes you on a journey through the city’s rich history and culture. You’ll stroll through the charming streets, admire the stunning architecture, and learn about Siena’s fascinating past.
The tour culminates at the iconic Piazza del Campo, where you can soak in the vibrant atmosphere and take in the breathtaking views.
Whether you’re a first-time visitor or a seasoned traveler, this guided tour is the perfect way to discover the beauty and charm of Siena. With availability from July 2021 to March 2026, you can plan your visit at a time that suits you best.
Don’t miss this opportunity to explore one of Italy’s most captivating destinations.
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Siena: Private Guided Tour of the Duomo Di Siena
Eager to witness the architectural splendor and artistic wonders of the Duomo di Siena? Consider the Siena: Duomo di Siena Private Guided Tour, a captivating 2-hour exploration of this UNESCO World Heritage Site.
Priced at €137.50 per person, this private experience grants you skip-the-line access and the insights of a knowledgeable local guide.
Explore the cathedral’s rich history and admire the works of renowned artists like Donatello, Michelangelo, and Bernini.
Discover the Cappella del Voto, high altar, intricate marble mosaic floor, and the Piccolominis Library.
With wheelchair accessibility and a dress code to cover shoulders and knees, this tour caters to diverse travelers.
While reviews suggest varying opinions on value, service, and organization, the guide’s informative and entertaining commentary often receives praise.
Consider this option for an immersive exploration of Siena’s architectural gem, the Duomo di Siena.
Read our full review: Siena: Private Guided Tour of the Duomo Di Siena Review
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Siena Guided Tour With Cathedral and Optional Crypt & Museum
For those captivated by the architectural splendor and artistic wonders of the Duomo di Siena, the Siena Guided Tour with Cathedral and Optional Crypt & Museum offers an enriching exploration of this UNESCO World Heritage Site.
Rated 4.5 stars and awarded a Badge of Excellence, this 2-3 hour walking tour welcomes a maximum of 12 guests for a personalized experience.
Led by knowledgeable and passionate guides, the tour highlights key historical landmarks, including Piazza San Domenico and the iconic Torre del Mangia.
Guests can skip the line to enter the breathtaking Siena Cathedral and opt to extend the tour with the OPA SI Pass for access to the Crypt and Museum.
While the cathedral may close unexpectedly, travelers can still soak in the beauty of the unfinished façade at their own pace.
With morning and afternoon start times, and free cancellation up to 24 hours in advance, this tour provides an excellent opportunity to explore Siena’s rich cultural heritage.
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Siena: Chianti Classico Guided Cycling Tour
Departing from the historic city of Siena, the Chianti Classico Guided Cycling Tour offers an exhilarating way to explore the renowned wine region.
This 6-hour activity is suitable for all fitness levels, with road and electric bikes available. Cyclists will ride at their own pace, admiring the stunning vineyard views along the way.
The tour is led by a knowledgeable, English-speaking guide who’ll share insights into the Chianti Classico area. Cyclists will have the opportunity to stop for photos and visit local cafés.
Lunch and refreshments are included, as are helmets, water, and insurance.
With a free cancellation policy up to 24 hours in advance, this tour provides a flexible and hassle-free experience.
Priced from $174.83 per person, it’s an excellent way to discover the beauty and flavors of the Chianti Classico region by bike.
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Lapi&Tour Guided Tour of the Cellars With Wine Tasting
Nestled among the rolling hills of Siena, the Lapi&Tour Guided Tour of the Cellars With Wine Tasting offers visitors a chance to explore the world of family-owned winery San Giorgio a Lapi.
The tour includes a guided exploration of the winery’s cellars and a wine tasting paired with local delicacies. Travelers can expect scenic views of the vineyards and olive groves as they learn about the winemaking process from the knowledgeable guides.
With a maximum of 10 participants, the tour provides a personalized experience. The tour starts at 11 a.m., and travelers should arrive 10 minutes early. The meeting point is the winery itself, and the tour ends at the same location.
The tour is wheelchair accessible, and stroller and infant seat availability is provided. Priced at $63 per person with a lowest price guarantee, the tour includes brunch, alcoholic beverages, and bottled water.
Guests have praised the informative and friendly guides, the exceptional food and wine pairings, and the overall high-quality experience.
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Siena: Private Custom Tour With a Local Guide
Offering a personalized exploration of Siena, the private custom tour with a local guide allows visitors to tailor their experience based on personal interests.
With tour durations ranging from 2 to 8 hours, travelers can choose the length that best suits their schedule. Prices start at $56.56 per person, and the tour is available in English, Italian, and Spanish.
Pickup is included from centrally located hotels, and the tour is wheelchair accessible. Booking is flexible, with the option to reserve now and pay later, as well as free cancellation up to 24 hours in advance.
Guides contact participants beforehand to customize the itinerary, ensuring a unique and engaging experience.
Highlights include gaining local insights into Siena’s culture, history, and daily life, visiting both main attractions and hidden gems, and receiving personalized recommendations on dining and other activities.
With an overall rating of 4.2/5 from 50 reviews, the tour offers excellent value for money and the opportunity to take in the charming city of Siena.
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Private Guided Tour of Siena With a Licensed Local Tour Guide
Although Siena boasts an abundance of history and culture, exploring its winding medieval streets can be overwhelming without a knowledgeable guide. The Private Guided Tour of Siena with a Licensed Local Tour Guide offers an in-depth exploration of this enchanting Italian city.
Led by the highly-rated Chiara, this 3-hour walking tour takes visitors through Siena’s most iconic landmarks, including the Duomo, Piazza del Campo, and the Churches of St. Dominic and St. Catherine.
Chiara’s extensive knowledge of Siena’s rich history and culture enhances the experience, providing fascinating insights into the city’s past.
The tour also delves into the significance of the Palio, Siena’s famous horse race that has captivated the city for centuries.
With a flexible itinerary and the option to include entrance fees, this private tour ensures an exclusive and customizable experience.
Whether you’re marveling at the Duomo’s Gothic architecture or strolling through the charming narrow streets, this guided tour promises an unforgettable journey through the heart of medieval Siena.
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From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch
Departing from Siena, the Brunello di Montalcino Guided Wine Tour with Lunch offers an immersive exploration of Tuscany’s renowned wine region. This 9-hour tour takes visitors to the medieval town of Montalcino, highlighting its fortress and charming streets.
The itinerary includes visits to three local wineries, providing opportunities for professional tastings and tours. Guests can look forward to a traditional Tuscan lunch at the family-run Molino di Sant’Antimo winery.
The tour also includes a visit to the peaceful Abbey of Sant’Antimo, known for its stunning Tuscan landscapes. With roundtrip transportation from Siena and an English-speaking guide, this tour is ideal for couples, groups, solo travelers, and families.
The tour receives high praise for its knowledgeable guides and value for money, though some participants suggest fewer stops in Montalcino to focus more on the winery experiences.
Read our full review: From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch Review
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Guided Walking Tour of Siena With Cathedral
The Guided Walking Tour of Siena With Cathedral provides visitors with a comprehensive exploration of the historic city’s renowned landmarks.
On this 2-hour tour, a local professional guide leads groups of up to 25 travelers through Siena’s top sights, including the iconic Piazza del Campo, the town hall, the Basilica of San Domenico, and the magnificent Siena Cathedral.
At the cathedral, participants can marvel at masterpieces by renowned artists like Donatello and Bernini. The tour includes the cathedral’s entrance ticket, except on Sundays when an alternative museum visit is offered.
Priced affordably at €40.00 per person, this guided experience offers a budget-friendly way to discover Siena’s rich history and architecture.
While not wheelchair accessible, the tour is stroller-friendly and conveniently located near public transportation.
Reviews praise the guides’ knowledge and engaging storytelling, though some note issues with audio clarity and language switching.
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Siena: Guided Bike Tour of Val D’Orcia
For those seeking to explore the picturesque countryside surrounding Siena, the Siena: Guided Bike Tour of Val d’Orcia offers an immersive experience. This 6-hour private tour departs from the charming village of San Quirico d’Orcia, with an English-speaking guide leading the way.
Suitable for all fitness levels, the tour provides options for e-bikes, road bikes, gravel bikes, or mountain bikes, catering to individual preferences.
Participants will have the opportunity to pedal through the stunning Val d’Orcia region, stopping at the medieval village of Pienza and other quaint settlements. The tour allows for photo breaks and a flexible pace, ensuring a comfortable and enjoyable journey.
An optional lunch and wine tasting at a Brunello di Montalcino winery can also be booked.
The tour includes essential amenities such as helmets, water, and insurance, along with the bike rental. However, it’s important to note that the tour isn’t suitable for children under 12 or pregnant women.
Read our full review: Siena: Guided Bike Tour of Val D’Orcia Review
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Guided Siena Tour With Lunch in Winery – Private Experience
This private guided tour in Siena offers an immersive experience, allowing visitors to explore the city’s rich history and culture while enjoying a delectable lunch at a renowned winery.
The tour begins with a walking exploration of Siena’s top sights, including the iconic Siena Cathedral, known for its stunning Gothic architecture. Guests will then venture to a nearby winery, where they’ll savor a traditional Tuscan lunch paired with the region’s acclaimed wines.
The small-group setting ensures personalized attention from the knowledgeable guide, who’ll provide insights into Siena’s art, architecture, and local traditions.
This 9-hour experience is priced at $185.12 per person, making it an excellent value for those seeking an in-depth, authentic look at Siena and its winemaking heritage.
With a 4.9-star rating from 328 reviews, this tour is a top-rated option for travelers seeking a well-rounded, private tour in the heart of Tuscany.
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Private Tour: Guided Hike in Tuscany With Transport From Siena
Embarking on a private guided hike through the breathtaking Tuscan countryside, this immersive experience whisks travelers away from the bustling streets of Siena.
With a 5.0 rating from 7 reviews, the tour offers a day-long adventure exploring the Chianti region‘s picturesque vineyards, charming villages, and rolling hills.
Led by an expert guide, the tour begins with a ride in an air-conditioned minivan from the meeting point in Piazza San Domenico, Siena.
Along the hike, guests enjoy a picnic lunch featuring local specialties like prosciutto, fresh vegetables, cheese, and bread, accompanied by regional wine.
The tour also includes a visit to the medieval town of San Gimignano, known for its iconic Gothic towers, as well as a stroll along the ancient pilgrimage route of Via Francigena.
Suitable for individuals in good physical condition, the tour requires a moderate fitness level and comfortable walking shoes.
With hotel pickup and drop-off, round-trip transportation, and free cancellation available, this guided hike in Tuscany promises an unforgettable experience.
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Ride and Cook Like a Tuscan Is an Amazing Guided Bike Tour
Enjoy the Tuscan lifestyle on this guided bike tour that allows you to ride and cook like a local.
Explore the picturesque countryside of Chianti, cycling through vineyards and olive groves. Stop at a local farm or winery to learn traditional Tuscan cooking techniques and prepare a delicious multi-course meal using fresh, seasonal ingredients.
This small-group tour, limited to 10 participants, provides an intimate and authentic experience. Your expert guide will lead you on scenic routes, sharing insights into the region’s history and culture.
Along the way, you’ll visit charming villages, stop for tastings of world-renowned Chianti wines, and enjoy breathtaking vistas.
At the end of the day, you’ll savor the homemade meal you helped prepare, paired with local wines, as you bask in the glory of the Tuscan landscape.
This unique tour offers an unparalleled opportunity to learn about the essence of Siena and its surrounding countryside.
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Siena Like a Local (With a Licensed Tour Guide)
Explore the enchanting city of Siena with a licensed tour guide on the “Siena Like a Local” experience. This 2-hour walking tour takes you on a journey through Siena’s rich history and culture, revealing hidden gems that only a local would know.
Starting at the iconic City Hall tower, you’ll explore Siena’s past, learning about its medieval architecture and traditions. The tour culminates at the stunning Il Campo, Siena’s famous central square.
With a maximum of 10 participants, you’ll enjoy a personalized and enriching experience led by a knowledgeable guide. Along the way, you’ll have the opportunity to ask questions and gain insider insights that will deepen your appreciation for this captivating Italian city.
Whether you’re a first-time visitor or a seasoned traveler, the “Siena Like a Local” tour offers an immersive and memorable way to explore the charming streets of this UNESCO World Heritage site.
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Guided Walking Tour of the Streets of Siena With Aperitif
Discover the enchanting streets of Siena on this guided walking tour that concludes with an aperitif. Priced at $101.84 per person, this tour takes you through the historic city with a maximum group size of 14 travelers.
You’ll meet at Piazza San Domenico, under the big tree, at 5:30 pm and end your journey on Via di Città.
During the tour, you’ll enjoy an aperitif with alcoholic beverages and snacks. The experience is wheelchair and stroller accessible, and transportation is also wheelchair-friendly. Infants can join, sitting on laps, with infant seats available.
This tour comes highly recommended, with a 5.0 rating based on a single review. With free cancellation up to 24 hours before the start, you can book with confidence.
Whether you’re a solo traveler or part of a group, this guided walking tour is an excellent way to explore the charming streets of Siena.
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2 Hour Private Walking Tour in Siena With Local Guide
This 2-hour private walking tour in Siena offers travelers an intimate exploration of the city’s rich history and picturesque landmarks with the guidance of a local expert.
Priced at $157.49 per person, the tour departs from the Basilica Cateriniana San Domenico and concludes at the iconic Piazza del Campo, home to the Mangia Tower.
Along the way, guests will have the opportunity to admire the stunning Siena Cathedral, with the tour including up to 10 euros per person for entrance fees.
The walking route is wheelchair and stroller accessible, ensuring the tour is inclusive for all.
With a perfect 5-star rating from 2 reviews, this guided experience is an excellent choice for those seeking an in-depth introduction to Siena’s history and landmarks.
Confirmation is received within 48 hours of booking, subject to availability, and guests can take advantage of the free cancellation policy up to 24 hours before the start of the tour.
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Guided Winery Tour and Wine Tasting in Siena
For those seeking a deeper connection to Siena’s winemaking heritage, the Guided Winery Tour and Wine Tasting offers an immersive experience.
Travelers are led through the organic vineyards and wine cellar of Azienda Agricola La Lastra, where they’ll learn about the region’s viticulture and sample five distinctive local wines.
With a maximum group size of 12, the tour provides an intimate and educational opportunity. Knowledgeable guides like Maya and Gianluigi lead the way, sharing insights into the winemaking process.
Guests can expect to savor a seasonal Tuscan meal, complemented by the wines. The tour’s 100% recommendation rating and Badge of Excellence attest to its quality.
Conveniently located just outside Siena, the winery offers free parking and WiFi. Participants can take advantage of the flexible cancellation policy up to 24 hours in advance.
At $78.74 per person, this guided experience offers an excellent value for wine enthusiasts visiting the region.
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Guided Tour of Castiglione Della Pescaia
Travelers exploring the picturesque coastal town of Castiglione della Pescaia can embark on a guided tour that unveils its rich history and natural beauty.
The tour is private, ensuring a personalized experience, and is led by a professional and certified tourist guide. The meeting point is in the town itself, and the tour returns to the same location.
The tour is priced at £123.53 for a group of up to 15 people, offering excellent value. Customers can take advantage of the free cancellation policy up to 24 hours before the experience starts, and the lowest price is guaranteed.
Transportation to the starting point is provided, and the tour is wheelchair and stroller accessible, with infant seats available.
Participants should be in moderate physical condition, as there are no major health or fitness requirements.
The tour has received positive reviews, with an overall rating of 4.5 stars, though the number of reviews is limited.
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Vespa Tour in Tuscany (Guided)
Exploring the rolling hills and charming towns of Tuscany aboard a classic Vespa scooter offers an unforgettable way to experience the region’s beauty. This guided Vespa tour in Siena, Italy, provides a thrilling and immersive adventure for visitors. The tour includes a Vespa rental, helmets, and a knowledgeable guide to lead the way through the picturesque Tuscan countryside.
Travelers can choose to meet the tour group directly at the starting point or opt for hotel pickup in the Siena area. The tour lasts approximately 5-6 hours, beginning at 9:30 am and ending back at the starting point. Along the way, you will enjoy a delicious lunch and have the opportunity to visit charming villages and landmarks.
While the tour isn’t recommended for those with certain medical conditions or pregnant travelers, it does require a moderate level of physical fitness.
With a 4.0 rating based on one review, this Vespa tour in Tuscany promises an unforgettable and exhilarating way to explore the region’s natural beauty.
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Siena Private Guided Tour for Families
What better way to explore the historic city of Siena than with a private guided tour designed specifically for families? At just $220.48 per group of up to 6 people, this tour offers exceptional value.
You’ll be met at Piazza San Domenico, in front of the stairs of the basilica, and guided through the city’s winding streets, learning about its rich history and culture. The tour includes entrance tickets and tips, ensuring a seamless experience.
The tour culminates at the iconic Piazza del Campo, home to the Fonte Gaia fountain. With wheelchair and stroller accessibility, plus the option to bring service animals, this tour is inclusive and accommodating for all.
Boasting a perfect 5-star rating across 5 reviews, you can trust you’re in good hands. Booking is easy, with confirmation within 48 hours and a free cancellation policy up to 24 hours in advance.
Don’t miss the chance to discover Siena’s beauty and charm on this family-friendly private tour.
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Recap
Siena offers a range of guided tours that cater to diverse interests. From exploring the iconic Duomo and Piazza del Campo to indulging in the city’s food and wine, there’s something for all. Whether you prefer a private tour or a group experience, Siena’s guided tours provide an immersive and educational way to discover the city’s rich history and cultural heritage.