The historic center of Siena is best explored with knowledgeable local guides who bring its medieval stories to life. The most rewarding tours focus on the city’s stunning landmarks – particularly the striped marble Duomo and the shell-shaped Piazza del Campo. We especially favor walking tours that combine the main sights with hidden backstreets, offering the perfect mix of history and local character. For families, the interactive tours featuring Siena’s colorful Contrade (districts) keep kids engaged while parents soak in the architecture. Those wanting to venture beyond the city walls will appreciate the combo tours that pair urban exploring with Tuscan wine tasting or countryside Vespa rides. Read on for our carefully selected top tour recommendations.
Good To Know
- Siena Guided Tours offer immersive experiences exploring the city’s history, architecture, and cultural heritage through small group tours led by expert local guides.
- Specialized tour options include in-depth Siena Cathedral explorations, family-friendly walking tours, Vespa countryside excursions, and self-guided audio experiences.
- Wine tours and tastings at family-owned wineries provide personalized insights into the local winemaking process and Tuscan culinary delights.
- Tours cater to diverse needs, with accessibility options, flexible pacing, and competitive pricing with free cancellation policies.
- Customizable private tours and guided bike adventures in Chianti allow for a tailored exploration of Siena and the surrounding region.
Discover Siena With Its Cathedral Guided Tour
Immersing visitors in Siena’s rich history and architectural wonders, the Siena Guided Tour with Cathedral and Optional Crypt & Museum offers an enriching exploration of the city’s most iconic landmarks.
Boasting 72 reviews and a Badge of Excellence, this small group tour provides a personalized experience, with pre-reserved skip-the-line tickets to the Siena Cathedral.
Led by expert local guides, the 2 to 3-hour walking tour unveils insights into the 17 Contrades and the renowned Palio competition.
Travelers can opt to visit the Crypt and Museum, or climb the unfinished cathedral façade at their own pace.
Despite occasional closures and limited accessibility, this tour promises an immersive journey through Siena’s captivating past.
Read our full review: Discover Siena With Its Cathedral Guided Tour Review
Book now: Check availability
Private Guided Tour of Siena With a Licensed Local Tour Guide
Wandering through Siena’s medieval streets alongside a licensed local tour guide unlocks a personalized exploration of the city’s storied past and architectural gems.
This private guided tour boasts a 100% recommendation rate from 13 travelers, granting an intimate experience to discover the highlights of the historic town.
Visitors will marvel at the Duomo, Piazza del Campo, and the Churches of St. Dominic and St. Catherine of Siena while learning about Siena’s rich culture and famed Palio.
With a flexible itinerary, the knowledgeable guide ensures a tailored journey catering to the group’s interests.
Maintaining a moderate fitness level, this tour offers unparalleled access to Siena’s medieval charm and beauty.
Read our full review: Private Guided Tour of Siena With a Licensed Local Tour Guide Review
Book now: Check availability
Private Guided Tour to the Cathedral and Its Amazing Marble Floor
The private guided tour to Siena Cathedral transports visitors into the heart of the city’s architectural splendor, offering an in-depth exploration of its remarkable marble floor.
Operated by Busillo Michele, the 11:00 am tour provides a private guide who uses a whisper and headset system to ensure social distancing while sharing insights.
Guests meet at Piazza del Duomo, where they’ll enter the cathedral and witness the stunning marble flooring up close.
The tour is wheelchair and stroller accessible, and the cathedral entrance ticket is included.
With a perfect 5-star rating from 9 reviews, this guided experience is a must for those seeking an immersive look at Siena’s iconic cathedral.
Read our full review: Private Guided Tour to the Cathedral and Its Amazing Marble Floor Review
Book now: Check availability
Guided Walking Tour of Siena With Cathedral
Explore the captivating city of Siena with a guided walking tour that highlights its iconic Cathedral. This 3.7-rated experience provides an immersive look into Siena’s rich history and culture.
Led by knowledgeable local guides, the tour takes visitors to the Piazza Salimbeni, home to Sallustio Bandini’s statue, and culminates at the stunning Siena Cathedral.
Reviewers praise the guides’ ability to share engaging historical insights, from the Palio horse race to local customs. While some note language barriers and tour length, the overall feedback indicates a satisfying experience for most travelers.
Accessibility is limited, but the tour remains a recommended way to discover Siena’s architectural and cultural gems.
Read our full review: Guided Walking Tour of Siena With Cathedral Review
Book now: Check availability
Siena Like a Local (With a Licensed Tour Guide)
Enjoy the heart of Siena with a locally-led tour that showcases the city’s rich history and vibrant culture.
The “Siena like a Local” experience provides an intimate look at this enchanting Italian gem. Led by a professional, licensed guide, you’ll explore the city’s iconic landmarks, including the impressive City Hall tower, and uncover hidden gems that only locals know.
With a maximum of 10 travelers, this tour offers a personalized experience perfect for those seeking an authentic Sienese adventure. Accessible by public transportation and suitable for most visitors, this tour is a must for anyone looking to discover Siena like a true insider.
Read our full review: Siena Like a Local (With a Licensed Tour Guide) Review
Book now: Check availability
Siena Private Walking Tour With A Professional Guide
Set out on a captivating private walking tour of Siena’s enchanting medieval cityscape with a knowledgeable local guide.
This approximately 2-hour experience offers a deep dive into the city’s key historical sights, including the iconic Piazza del Campo, the Basilica of St. Francis, and the Medici Fortress.
Eschew the hassle of navigating with a map, as the guide leads you through the old town, sharing insights and anecdotes along the way.
The tour is fully customizable to your group’s interests, and entrance fees as well as gratuities are included in the competitive per-group pricing.
With flexible start times and a wheelchair-accessible meeting point, this tour caters to diverse travel needs.
Read our full review: Siena Private Walking Tour With A Professional Guide Review
Book now: Check availability
Guided Tour of Castiglione Della Pescaia
Visitors to Siena’s enchanting medieval streets can extend their exploration to the nearby coastal town of Castiglione della Pescaia.
A guided tour takes travelers through this picturesque fishing village, led by a professional and certified guide. The private tour ensures a personalized experience, with only your group participating.
Accessible by wheelchair and stroller, the tour caters to diverse needs. Moderate fitness is required, as there are no heart problems or serious medical conditions.
Priced at ₹13,149.34 for up to 15 people, the tour provides a 4.5-rated experience, with free cancellation up to 24 hours before.
Explore Castiglione della Pescaia’s charm and natural beauty on this exceptional guided tour.
Read our full review: Guided Tour of Castiglione Della Pescaia Review
Book now: Check availability
Guided Walking Tour of the Streets of Siena With Aperitif
On the iconic streets of Siena, travelers can partake in an engaging guided walking tour that delves into the city’s rich history and captivating architecture.
This 5:30 pm experience includes a stop for an aperitif with snacks, allowing participants to savor the local flavors.
The tour is capped at 14 travelers, ensuring personalized attention from the guide.
With free cancellation and flexible rescheduling, this tour offers convenience and accessibility, catering to various needs, including wheelchair users and those with strollers.
Highly rated by past guests, this walking exploration of Siena’s charming streets provides an immersive and enriching experience for visitors.
Read our full review: Guided Walking Tour of the Streets of Siena With Aperitif Review
Book now: Check availability
Siena Private Guided Tour for Families
Siena’s historic streets come alive on this private guided tour tailored for families.
With a 5.0 overall rating from 3 reviews, this 3-hour experience offers an intimate look at the city’s top sights. The tour starts at Piazza San Domenico and winds through the charming medieval alleyways, culminating at the iconic Piazza del Campo.
Along the way, your private guide will share insights into Siena’s rich history and culture. The tour is wheelchair and stroller accessible, making it an ideal choice for travelers with mobility needs.
Priced at $226.31 for up to 6 people, this tour provides excellent value with tips included and free cancellation up to 24 hours in advance.
Read our full review: Siena Private Guided Tour for Families Review
Book now: Check availability
Vespa Tour in Tuscany (Guided)
For an exhilarating way to explore the picturesque Tuscan countryside, one can embark on a guided Vespa tour in Siena.
This 4.0-rated activity allows visitors to rent a Vespa, don a helmet, and follow a mounted guide through the region’s charming towns and rolling hills.
The tour includes transportation to and from the meeting point, fuel, and all necessary equipment.
With a moderate physical fitness level required, the experience isn’t recommended for pregnant travelers or those with heart problems.
Participants will be picked up from their hotel or a designated meeting point, and the tour returns to the starting location, providing a seamless and immersive journey through the beauty of Tuscany.
Read our full review: Vespa Tour in Tuscany (Guided) Review
Book now: Check availability
From Siena’s Golden Age to Glory: A Self-Guided Audio Tour
Explore Siena’s captivating history through a self-guided audio tour that takes visitors on a journey from the city’s Golden Age to its present-day glory.
Titled “From Siena’s Golden Age to Glory,” this VoiceMap audio tour offers lifetime access, with detailed starting point instructions and offline accessibility via the mobile app.
While tickets and transportation aren’t included, the tour is stroller-accessible, though not wheelchair-friendly.
Operational from July 2020 to July 2025, the tour has received a single review, which cited technical issues with the app.
To ensure a smooth experience, visitors should install the VoiceMap app before arrival and confirm the start time with the local provider.
Read our full review: From Siena’s Golden Age to Glory: A Self-Guided Audio Tour Review
Book now: Check availability
Siena : Private Custom Tour With a Local Guide
Travelers eager to uncover Siena’s unique charm can embark on a private custom tour with a knowledgeable local guide.
This 2.5-hour walking tour allows visitors to explore the city at their own pace, with a tailored itinerary based on their preferences. The guide will meet travelers at their centrally located accommodation and assist with booking any desired visits.
The tour includes a drink or food break, and travelers can expect a smooth, accessible experience, with the option to conclude the tour at a different location.
While reviews are limited, this tour provides a personalized way to discover Siena’s rich history and hidden gems.
Read our full review: Siena: Private Custom Tour With a Local Guide Review
Book now: Check availability
Siena Self-Guided Audio Tour
This self-guided audio tour of Siena provides travelers with a flexible and affordable way to explore the city’s rich history and iconic landmarks at their own pace.
Featuring 12 attractions with private access to audio guides and a tour map, the tour allows visitors to start and end wherever they choose.
While entry fees are required at some sites, the audio links are valid for up to 6 days, enabling travelers to take their time.
However, the tour isn’t suitable for those who prefer guided experiences or continuous listening, and it’s not wheelchair accessible.
With a 2.0 rating based on 5 reviews, the audio tour’s quality and content have received mixed feedback, though the host encourages listening to all guides before forming conclusions.
Read our full review: Siena Self-Guided Audio Tour Review
Book now: Check availability
Have You Ever Taken a Guided Tour of Siena?
Many travelers have discovered the joy of exploring Siena’s rich history and iconic landmarks through guided tours.
The city’s Basilica Cateriniana San Domenico serves as the meeting point for a highly-rated 5.0 tour that’s recommended by 100% of participants.
Operating year-round, the tour takes visitors on a journey through Siena’s picturesque streets, culminating at the stunning Piazza del Campo.
Priced at €60.00 per group of up to 15 people, the tour offers free cancellation and a “reserve now, pay later” option.
While not wheelchair accessible, the tour is suitable for most travelers, including infants.
With its convenient scheduling and positive reviews, this guided tour is an excellent way to experience the beauty and history of Siena.
Read our full review: Have You Ever Taken a Guided Tour of Siena? Review
Book now: Check availability
Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum
Siena’s iconic Duomo and renowned museums offer visitors a captivating glimpse into the city’s rich cultural heritage.
The “Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum” allows travelers to explore these treasures with the expertise of local guides. Priced reasonably at $32.33 per person, the tour provides insights into Siena’s history, architecture, and cuisine, including recommendations for the renowned Brunello wine.
While the cathedral tour is currently unavailable due to COVID-19 restrictions, the flexible booking policy and maximum group size of 20 ensure a personalized experience.
Despite some logistical challenges, the tour’s highly-rated guides and immersive content make it a compelling option for those seeking to explore Siena’s captivating story.
Read our full review: Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum Review
Book now: Check availability
Lapi&Tour Guided Tour of the Cellars With Wine Tasting
For those seeking an immersive wine experience in Siena, the “Lapi&Tour Guided Tour of the Cellars With Wine Tasting” offers a captivating glimpse into the region’s rich winemaking tradition.
This family-owned winery in Siena invites visitors to explore its scenic vineyards and olive groves before embarking on a guided tour of the cellars. During the tasting, knowledgeable guides share insights into the wine-making process and pair the wines with local delicacies.
With a maximum of 10 participants, the tour provides an intimate and personalized experience. Wheelchair accessibility, on-site transportation, and a 15% discount on purchases of 6 bottles or more make this tour an attractive option for oenophiles and casual wine enthusiasts alike.
Read our full review: Lapi&Tour Guided Tour of the Cellars With Wine Tasting Review
Book now: Check availability
Siena Scavenger Hunt and Best Landmarks Self-Guided Tour
Amidst the captivating medieval architecture and winding streets of Siena, the “Siena Scavenger Hunt and Best Landmarks Self-Guided Tour” offers a unique and engaging way for visitors to explore the city’s rich history and iconic landmarks.
With an overall rating of 5.0 based on positive reviews, this self-guided tour provides travelers with the World City Trail app, navigation, and information on the top sights.
Priced at just $4.31 per person, the tour can be enjoyed daily from 12:00 AM to 11:30 PM, making it a flexible and budget-friendly option.
Whether you’re looking to discover Siena’s hidden gems or learn about its fascinating past, this scavenger hunt tour is an excellent choice.
Read our full review: Siena Scavenger Hunt and Best Landmarks Self-Guided Tour Review
Book now: Check availability
Guided Winery Tour and Wine Tasting in Siena
Situated just outside the historic city of Siena, the “Guided Winery Tour and Wine Tasting” offers visitors an immersive experience into the heart of Tuscan winemaking.
This highly-rated tour takes guests on a journey through the organic vineyards and wine cellar of Azienda Agricola La Lastra, providing a comprehensive education on the region’s winemaking process.
Travelers are treated to a sensorial tasting of five organic wines, accompanied by a delectable lunch featuring fresh, seasonal Tuscan cuisine.
With knowledgeable guides, stunning vineyard views, and exceptional wine and food pairings, this tour is a must-do for both wine enthusiasts and novices seeking an authentic taste of Siena’s viticultural heritage.
Read our full review: Guided Winery Tour and Wine Tasting in Siena Review
Book now: Check availability
2 Hour Private Walking Tour in Siena With Local Guide
Stepping away from the serene vineyards and into the heart of Siena’s historic city center, the “2 Hour Private Walking Tour in Siena With Local Guide” offers visitors an immersive experience that showcases the city’s architectural and cultural gems.
Priced at $161.65 per person, this private tour provides a personalized exploration, with a local guide leading the way through Siena’s iconic landmarks. Participants can enjoy snacks and skip the lines at the Duomo, as they discover the city’s rich history and vibrant atmosphere.
With a 5.0 overall rating, the tour is wheelchair and stroller accessible, making it suitable for most travelers seeking an in-depth perspective of this enchanting Italian destination.
Read our full review: 2 Hour Private Walking Tour in Siena With Local Guide Review
Book now: Check availability
4-Hour Guided Bike Tour for Small Groups in Chianti
The 4-Hour Guided Bike Tour for Small Groups in Chianti offers a unique opportunity to explore the picturesque Chianti region outside of Siena.
The small group size of up to 8 travelers ensures a personalized experience led by a knowledgeable cycling guide. Participants will be provided with bikes, helmets, and bottled water, as well as private transportation to and from the meeting point in Siena.
The tour isn’t recommended for those with physical limitations, but it’s perfect for moderately fit travelers who want to enjoy the stunning Tuscan countryside.
The tour starts at 9 AM, with confirmation received within 48 hours of booking, subject to availability.
Read our full review: 4-Hour Guided Bike Tour for Small Groups in Chianti Review
Book now: Check availability
2 Hour Siena Private Guided Walking Tour
Discover the captivating history and architectural marvels of Siena on this 2-hour private guided walking tour.
Led by a licensed guide specializing in Siena, you’ll explore the city’s UNESCO World Heritage Site, known for its stunning Gothic architecture and rich cultural heritage.
Visit key sites like the iconic Piazza del Campo, home to the annual Palio horse race, the magnificent Siena Cathedral, and the historic Via Francigena.
Explore the medieval neighborhoods and learn about the local lifestyles.
This private experience is ideal for larger groups of up to 15 travelers, with a flat fee covering the entire group.
Easily accessible by public transportation, this tour is a must-do for those seeking an in-depth exploration of Siena’s wonders.
Read our full review: 2 Hour Siena Private Guided Walking Tour Review
Book now: Check availability
Highlights of Siena Private City Tour With Local Guide
Embarking on a captivating private city tour of Siena, travelers explore the rich cultural heritage and architectural wonders of this enchanting Italian city.
Operated by Orange Umbrella Tours, the tour provides an English-speaking local licensed guide who leads guests through the highlights, including the renowned Duomo of Siena and the iconic Torre del Mangia.
With hotel pickup and drop-off, the experience is seamless, and travelers can explore at their own pace.
Though non-refundable, the tour’s price of $246.78 per person offers excellent value, and the Lowest Price Guarantee ensures a competitive rate.
While not wheelchair accessible, the tour caters to most travelers, providing an immersive and unforgettable exploration of Siena’s captivating charm.
Read our full review: Highlights of Siena Private City Tour With Local Guide Review
Book now: Check availability
Frequently Asked Questions
What Is the Average Duration of the Guided Tours in Siena?
The average duration of guided tours in Siena is typically between 2-3 hours. This allows visitors ample time to explore the city’s historic landmarks, medieval architecture, and learn about its rich cultural heritage from knowledgeable local guides.
Are There Any Discounts or Package Deals Available for Guided Tours?
Guided tour providers in Siena often offer discounted rates for group bookings and combined packages that include admission to various attractions. Some tours may also provide student or senior citizen discounts to make the experience more accessible.
Can I Book a Private Tour for a Large Group or Family?
Yes, many tour providers offer private tours for large groups or families. They can customize the itinerary and pace to suit your group’s interests and needs. Just ask about their private tour options when booking.
Are There Any Child-Friendly or Accessible Guided Tour Options?
Yes, there are child-friendly and accessible guided tour options in Siena. Many tour companies offer tours tailored for families with children, including special activities and accommodations for those with mobility challenges or disabilities.
Do the Guided Tours Include Admission Fees to Any Attractions?
Most guided tours in Siena include admission fees to top attractions like the Duomo, Piazza del Campo, and Palazzo Pubblico. Some tours also offer child-friendly and accessible options, providing a well-rounded experience for visitors of all ages and abilities.
The Sum Up
Siena offers a range of guided tours that cater to different interests and preferences. From walking tours of the city’s historic center to cathedral visits and bike excursions in the surrounding Chianti region, travelers can discover Siena’s rich heritage and stunning architecture with the help of licensed local guides. These tours provide an engaging and informative way to explore one of Italy’s most captivating medieval cities.