The ancient city of Siena rewards visitors with exceptional guided experiences. After decades of exploring its medieval streets, several tours stand out as clear winners. The Duomo and City Walking Tour efficiently covers the must-see cathedral while skipping long entrance lines. For a peaceful escape, the countryside horseback tour reveals hidden corners of the Tuscan landscape. Two food-and-wine experiences deserve special mention: the Chianti wine tasting led by an expert sommelier, and the comprehensive food walking tour combining local specialties with cultural insights. For travelers seeking personal attention, the private medieval walking tour offers flexibility and deeper historical context. Read on for our carefully selected top tours in Siena.
Key Points
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Siena offers a variety of highly-rated walking tours, including the Siena Duomo and City Walking Tour, Private Walking Tour of Medieval Siena, and Walking Tour of Siena With Food & Chianti Wine.
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Culinary and food tours in Siena provide opportunities to explore local specialties, such as Chianti wine, Pecorino cheese, and homemade pasta, with options for tasting and guided experiences.
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Visitors can enjoy wine tours and tastings in Siena, including small-group tours led by sommeliers, Brunello di Montalcino wine tours, and educational experiences at organic wineries.
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Outdoor and adventure tours in Siena’s countryside offer activities like horseback riding, hiking along the Via Francigena, and electric bike tours through the Chianti hills.
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Tour booking information highlights the availability of flexible cancellation policies, small group sizes, and accessibility measures for an inclusive and personalized experience in Siena.
Skip the Line: Siena Duomo and City Walking Tour
The Skip the Line: Siena Duomo and City Walking Tour offers visitors a comprehensive introduction to the stunning city of Siena. This highly-rated tour, with a 94% recommendation rate and 4.8 overall rating, provides skip-the-line access to the Siena Duomo, a Gothic masterpiece featuring artworks by renowned artists.
Travelers will also explore the iconic Piazza del Campo, home to the thrilling Palio horse race, and visit the Basilica of San Domenico, a notable Gothic church.
Lasting around 2 hours, the tour is led by knowledgeable local guides who share insights into Siena’s rich history, architecture, and culture. With a maximum group size of 30, the experience is both informative and engaging.
The tour includes gratuities and hotel pickup and drop-off, making it a convenient way to discover Siena’s top attractions. Travelers praise the guides for their expertise, humor, and ability to bring the city’s stories to life.
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Siena: Horseback Riding Tour in the Siena Countryside
Although horse riding may not be the first activity that comes to mind when exploring the historic city of Siena, the Siena: Horseback Riding Tour in the Siena Countryside offers travelers a unique opportunity to experience the stunning countryside surrounding this enchanting Tuscan town.
Priced from $71.99 per person, this guided tour takes riders through picturesque vineyards, rivers, olive groves, and cypress tree-lined roads. The tour is suitable for all skill levels, with well-trained and calm horses ensuring a safe experience.
Participants can also opt for a riverside picnic or a wine tasting at a local winery, further seeing the region’s natural and cultural offerings.
With a 4.9/5 rating based on 122 reviews, the tour’s highlights include scenic routes, a knowledgeable guide, and the chance to learn about the local flora and fauna.
Certain restrictions apply, but overall, this horseback riding experience offers a unique and memorable way to explore the Sienese countryside.
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Siena: A Wine Tour and Tasting Experience
For travelers seeking a deeper immersion into Tuscany’s renowned wine culture, the Siena: A Wine Tour and Tasting Experience offers an exceptional opportunity.
This highly rated small-group tour boasts a 100% recommendation rate and a Badge of Excellence, promising an intimate exploration of the region’s organic vineyards and historical wine cellars.
Led by a knowledgeable sommelier, you will sample at least four local wines and enjoy a light Tuscan lunch featuring fresh seasonal ingredients.
The itinerary includes guided visits to organic vineyards, a sensorial tasting, and additional amenities like free parking, Wi-Fi, and bottled water.
With a maximum group size of 12, travelers can expect personalized attention.
While not wheelchair accessible, the tour does accommodate infants.
Positive reviews highlight the knowledgeable guides, delicious food and wine, and the stunning property.
Travelers seeking an authentic winery experience in Siena will find this tour highly recommended.
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Siena Food Tour and Chianti Wine
This Siena Food Tour and Chianti Wine experience offers travelers an immersive exploration of the city’s renowned culinary and wine heritage.
Priced at £63.35 per person, this 2.5-hour small-group tour (maximum 12 people) delves into the flavors that define Siena. Guests will savor local specialties like Chianti wine, Vernaccia white wine, Pecorino cheese, salami, and homemade pasta, along with an ice cream tasting from an award-winning shop.
The experience also includes panoramic views of Siena’s historic neighborhoods, the iconic Cathedral, and Piazza Salimbeni.
With free cancellation up to 24 hours in advance, this tour provides a flexible and convenient way to discover Siena’s food and wine scene. Reviewers praise the knowledgeable guide and the excellent combination of history, information, and delectable tastings.
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Discover the Medieval Charm of Siena on a Private Walking Tour
What better way to discover the medieval charm of Siena than on a private walking tour? This 2-3 hour experience led by a licensed local guide provides an in-depth look at the city’s storied past.
With 94% of travelers recommending the tour, you’ll explore the historic old town, including the iconic Piazza del Campo and Basilica of San Domenico.
The tour also offers an optional visit to the magnificent Siena Cathedral, home to breathtaking artworks by renowned masters.
Along the way, you’ll learn about the legendary Palio horse race and local traditions that have endured for centuries. Guests consistently praise the guides’ knowledge and passion, as well as the personalized attention and engaging storytelling.
Though the tour involves some steep hills, it’s wheelchair accessible and stroller-friendly.
With free cancellation up to 24 hours in advance and prices starting at $154.86 per person, this private walking tour is an excellent way to learn about Siena’s medieval splendor.
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Siena: Organic Winery Tour and Wine Tasting
Situated just 2 kilometers from the historic city of Siena, an organic winery beckons oenophiles and nature enthusiasts alike.
This 2.5-hour experience, priced at $77.13 per person, offers a guided tour of the vineyards and cellars, where visitors can learn about organic grape cultivation and winemaking techniques. The highlight is a tasting of 5 organic wines, complemented by a seasonal Tuscan lunch.
The tour showcases the winery’s commitment to sustainability and preservation, delving into the science behind its agro-ecosystem.
Travelers can expect a knowledgeable and engaging guide, who provides insights into the history, culture, and organoleptic nuances of the wines. With a 5/5 rating based on 63 reviews, the tour has earned rave reviews for its personal touches, such as accommodating dietary needs and special celebrations.
The experience starts at the St. della Befana n. 5 location in Siena, with tours available in both English and Italian.
Booking is flexible, with a full refund for cancelations up to 24 hours in advance.
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Vespa Tour With Lunch & Chianti Winery From Siena
While exploring the picturesque Chianti hills of Tuscany, travelers can embark on a full-day Vespa tour that combines the thrill of riding iconic scooters with the delights of a winery visit and a traditional Tuscan lunch.
Departing from Siena, this tour offers a comprehensive experience, with a route that passes through the charming village of Monteriggioni and explores the breathtaking Chianti region.
Participants will have the opportunity to test their skills on Vespa scooters, guided by professional tour escorts who provide a safety briefing and ensure a smooth ride.
The tour also includes a visit to a renowned Chianti winery, where guests can sample the region’s renowned wines during a guided tasting session.
To complement the day’s activities, a light lunch featuring fresh, locally sourced ingredients is served, catering to a range of dietary preferences.
With a 4.3 rating and 124 positive reviews, this Vespa tour is an excellent choice for those seeking an immersive and memorable experience in the heart of Tuscany.
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Siena: Walking Food Tour With Tastings
Visitors to Siena can enjoy the city’s rich culinary heritage by embarking on a walking food tour led by a local expert.
This 3-hour experience takes small groups of up to 12 participants on a culinary journey through the historic streets of Siena. Along the way, they’ll stop at the Siena Cathedral, Piazza del Campo, and the Basilica Cateriniana San Domenico, enjoying wine tastings, a full lunch, and sampling local specialties like charcuterie, Pici cacio e pepe, and Ricciarelli.
The tour is offered in both English and Italian, and is priced at $91.53 per person. Guests can take advantage of the free cancellation policy up to 24 hours in advance and the reserve now, pay later option.
With an impressive 4.9/5 rating based on 54 reviews, this walking food tour provides an authentic and delicious introduction to Siena’s renowned cuisine.
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Full-Day 2 Wineries Tour in Montepulciano With Tasting and Lunch
Embarking on a full-day journey, visitors can explore the renowned wine region of Montepulciano through a captivating two-winery tour. Boasting a 95% recommendation rate from 73 reviewers, this small-group experience offers a personalized taste of Tuscany beyond the popular destinations of Florence or Siena.
The tour includes hotel pick-up and drop-off, as well as visits to local wineries where guests can sample Brunello and other regional specialties. An included lunch in Montepulciano allows travelers to savor traditional Tuscan cuisine, complemented by the region’s acclaimed wines.
With a Badge of Excellence from Siena, the tour promises knowledgeable guides, stunning scenery, and a delightful overall experience.
While some reviews note timing and lunch expectations could be improved, the tour remains highly recommended for wine enthusiasts and those seeking to enjoy the heart of Tuscany.
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From Florence: San Gimignano, Siena, and Chianti Wine Tour
Departing from Florence, this comprehensive tour escorts visitors on an 11.5-hour journey through the picturesque Tuscan countryside, offering a glimpse into the region’s renowned wine, history, and medieval architecture.
Beginning at Villa Costanza, the tour heads to Siena for a guided exploration of its UNESCO-listed historic center, including the stunning Siena Cathedral and Palazzo Comunale.
Travelers then journey through the rolling Chianti Hills, culminating in a visit to a local winery for tastings and food pairings.
The tour also includes stops in the well-preserved medieval town of Monteriggioni and the iconic San Gimignano, known for its striking skyline of towers.
Throughout the day, multilingual guides share insights and allow ample free time for independent discovery.
With flexible booking options and a cancellation policy allowing for full refunds up to 24 hours in advance, this tour provides a seamless and memorable Tuscan experience.
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Tuscany Hiking Tour From Siena Including Wine Tasting
Nestled in the rolling hills of Tuscany, the Tuscany Hiking Tour From Siena Including Wine Tasting offers visitors a captivating blend of natural beauty, rich history, and local culture.
This half-day excursion takes travelers along the ancient Via Francigena, a pilgrimage route from Canterbury to Rome, culminating in the charming town of Monteriggioni for a wine tasting experience.
The tour starts at the Siena FS railway station, with transport provided by an air-conditioned minivan. Hikers will cover approximately 8 km (5 miles) over 3-4 hours, guided by an expert with in-depth knowledge of the local flora, fauna, and history.
The scenic hike through villages and vineyards showcases the region’s picturesque landscapes.
At the end of the trail, visitors are treated to a wine tasting at a local winery, sampling 3-4 organic wines.
With a 98% traveler recommendation rate, this tour is a must-do for those seeking an immersive experience in the heart of Tuscany.
Comfortable shoes and moderate fitness are recommended for this engaging and informative adventure.
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Siena : Highlights Private Walking Tour
Ideal for those seeking an immersive exploration of Siena’s iconic landmarks, the 3-hour Siena: Highlights Private Walking Tour offers a comprehensive introduction to the city’s Renaissance heritage.
Priced at €90 per person, this private tour allows visitors to customize the experience based on their interests, from the grand Siena Cathedral to the stately Palazzo Pubblico.
Led by knowledgeable local guides, the tour takes guests through the UNESCO-listed historic center, including lesser-known gems like the Basilica Cateriniana San Domenico and the charming Via Camporegio.
With its convenient starting point near the city’s main attractions, the tour provides valuable insights into Siena’s rich culture and architecture.
Wheelchair-accessible and with free cancellation up to 24 hours in advance, this private walking tour is a flexible and hassle-free way to discover the highlights of this remarkable Tuscan city.
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Exciting ATV Tour in the Tuscan Countryside
For travelers seeking an exhilarating way to explore the picturesque Tuscan countryside, the Exciting ATV Tour in the Tuscan Countryside offers an unparalleled experience.
With a 100% recommendation rate from 35 reviews, this small-group ATV excursion takes adventurers through the UNESCO-listed Crete Senesi area, from Chianti to Val d’Orcia.
The tour includes a briefing and test drive before setting off, ensuring participants feel comfortable operating the ATVs. Guided by experts, the experience provides assistance and answers to any questions that arise.
Despite the moderate physical fitness required, the tour is suitable for those 18 and older, who can don the provided sportswear and helmet.
Offering hotel pickup and drop-off, the tour includes all necessary equipment, fuel, and support, allowing guests to fully enjoy the scenic vineyard views and unique perspective of the Tuscan countryside.
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Siena: Food and Culture Guided Walking Tour
Explore Siena’s rich culinary and cultural heritage through the Siena: Food and Culture Guided Walking Tour. This 2-3 hour small group experience allows visitors to explore the city’s medieval history and savor its renowned local cuisine.
Skip the line and gain priority access to the stunning Siena Cathedral, where you’ll marvel at the intricate Gothic architecture and stained glass windows.
Next, wander through the charming streets of the historic center, stopping to sample traditional Sienese delicacies like artisanal cheeses, cured meats, and the region’s famous Chianti wines.
Along the way, your expert guide will share insights into Siena’s past as a powerful medieval city-state and explain the significance of landmarks like the Palazzo Pubblico.
With rave reviews from over 369 travelers and a 4.9 rating, this immersive tour is the perfect way to experience the true essence of Siena.
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Savor Siena Food and Wine Tour
This 3-hour small-group Savor Siena Food and Wine Tour provides an immersive culinary experience, allowing visitors to indulge in the region’s renowned Tuscan cuisine and wines.
Awarded the Badge of Excellence in Siena, Italy, the tour boasts a remarkable 100% recommendation rate from travelers. Guests can expect to sample local specialties like pecorino cheese, ciccino focaccia, and a selection of three distinct wines, including the historic white, Chianti Classico, and Vin Santo dessert wine.
The tour also includes a tasting of traditional Tuscan starters, such as bruschetta, cured meats, and local honeys, as well as a sampling of the iconic panforte cake and pepperbread for dessert.
With a maximum of 14 travelers, the tour offers a relaxed atmosphere for exploring Siena’s culinary heritage. Highly praised for its knowledgeable and friendly guides, the Savor Siena Food and Wine Tour provides an exceptional opportunity to take in the flavors of Tuscany.
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From Siena: Tuscany Hills Wine Tour
Travelers seeking to enjoy the picturesque Tuscan countryside and uncover the region’s enological treasures can embark on the From Siena: Tuscany Hills Wine Tour. This full-day excursion offers visitors a comprehensive exploration of the Tuscany Hills, with stops at renowned wineries, charming medieval towns, and scenic vistas.
The tour departs from Siena and travels to Monteriggioni, where guests visit a winery, taste three wines, and learn about olive oil production.
Next, they visit the town of Pienza for free time, lunch, and sightseeing. The final stop is Montepulciano, where participants explore the town, taste the renowned Nobile di Montepulciano wine, and visit a second winery.
Throughout the day, guests enjoy the comfort of an air-conditioned bus or minivan and the expertise of a knowledgeable guide.
With a rating of 4.1/5 based on over 300 reviews, this tour offers an excellent value at $97.70 per person and the flexibility of free cancellation up to 24 hours in advance.
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Walking Tour of Siena With Food & Chianti Wine
Why not discover Siena’s rich medieval heritage and indulge in its tantalizing culinary delights on a captivating walking tour? This highly-rated tour, with a 97% traveler recommendation, takes you on a journey through the UNESCO-listed Piazza del Campo and nearby monuments.
Led by a knowledgeable local guide, you’ll explore Siena’s stunning architecture and learn about its fascinating medieval history.
The tour’s culinary experience is a highlight, with opportunities to sample classic Tuscan fare and renowned Chianti wine. Savor a starter of Chianti Classico, followed by a delectable spread of Tuscan salami, prosciutto, Pecorino cheese, and homemade bread and jam.
The tour also includes a mouthwatering lunch of homemade pasta, Pecorino, organic jam, and Tuscan cold cuts. Top it off with an awarded gelato tasting, sure to delight your taste buds.
With a maximum of 12 travelers, this intimate walking tour promises an engaging and memorable experience, rain or shine.
Don’t miss the chance to uncover Siena’s hidden gems and indulge in its gastronomic delights.
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Siena: Educational Wine Tour & Tasting
Explore the renowned winemaking region surrounding Siena on this educational wine tour and tasting experience. Located just 2 km from the city center, this 3-hour tour takes you through an organic winery’s vineyards and historical cellar.
Learn about the agronomic, phenolic, and organic cycles of winemaking as you discover the winery’s low-impact agricultural practices.
During the sensory tasting, sample 4 of the winery’s organic wines and enjoy a light Tuscan-inspired lunch. The knowledgeable hosts provide simple explanations of the complex chemical and microbiological processes involved in wine production, ensuring an informative yet accessible experience.
With an impressive 5/5 overall rating from 189 reviews, this tour offers exceptional value, excellent service, and superb organization.
The meeting point is at Azienda Agricola La Lastra, located just a short distance from the center of Siena. Simply open the provided Google Maps link for easy navigation to this educational wine adventure.
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Vespa Tour in Chianti Small Group From Florence
One of the most popular tours in Siena is the Vespa Tour in Chianti, which takes small groups on a full-day adventure through the picturesque Tuscan countryside.
Departing from Florence, the tour allows participants to explore historic villas, medieval villages, olive groves, and vineyards while riding authentic Vespa scooters. The tour includes a visit to a local winery for a tasting of Chianti wines, as well as a light lunch featuring traditional Tuscan dishes.
To participate, riders must know how to operate a scooter and have a valid driver’s license. The tour isn’t suitable for pregnant travelers or those with certain medical conditions, and comfortable clothing is required.
While most reviews praise the stunning scenery and enjoyable guides, some past guests have raised concerns about customer service, unclear pickup locations, and handling of weather-related cancellations.
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Siena: Instant Photography City Tour
For travelers seeking a unique way to capture the historic charm of Siena, the Instant Photography City Tour offers a delightful experience. This 2-hour tour allows participants to explore the city’s iconic landmarks while learning the art of instant photography.
Equipped with a Polaroid camera, guests will be guided through the picturesque streets, capturing the essence of Siena’s medieval architecture and vibrant atmosphere.
The tour covers Siena’s top sights, including the Siena Cathedral, Palazzo Pubblico, and the famous Piazza del Campo. Along the way, the knowledgeable guide will provide insights into the city’s rich history and cultural significance.
Participants will have the opportunity to immortalize their journey with one-of-a-kind Polaroid snapshots, creating a unique memento to treasure long after the tour has ended.
With a rating of 4.7 out of 5 from 313 reviews, the Siena: Instant Photography City Tour is a must-try for photography enthusiasts and those seeking an immersive and creative way to discover the enchanting city of Siena.
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Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch
What better way to take in the renowned Brunello di Montalcino wine region than through a daylong winery tour? This specialized experience takes travelers to historic cellars and vineyards, offering an in-depth look at the production of this renowned Italian varietal.
Visitors can expect two winery tours and tastings, a pairing lunch at a historic winery, and transportation in a luxury air-conditioned vehicle. With a maximum group size of 8, the tour provides a personalized experience.
Pickup is available from several locations, and the day includes wheelchair accessibility and infant seats. An English-speaking driver, knowledgeable about the region and wines, is on hand throughout the tour.
Priced from $282.43 per person, the tour has earned an impressive 4.9 out of 5 rating based on 91 reviews, with 98% of travelers recommending the experience. Highlights include excellent wines, engaging guides, and beautiful scenery, as well as visits to boutique wineries for an authentic look at Brunello di Montalcino.
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From Siena: Chianti and Castles Tour With Wine Tastings
Departing from Siena, the Chianti and Castles Tour with Wine Tastings takes visitors on a captivating 5-hour exploration of the renowned Chianti region. Priced at $87.42 per person, this small-group tour (maximum 8 participants) promises an immersive experience, including guided tours, wine tastings, sightseeing, and scenic views.
Highlights include ancient churches, medieval castles, charming villages, and picturesque landscapes. Participants will visit Castellina in Chianti and two renowned wineries, where they’ll sample the signature Chianti blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon.
Transportation is provided via a climate-controlled minivan, and a knowledgeable, English- and Italian-speaking guide accompanies the group. Reviews praise the tour’s value, the guide’s expertise, and the overall enjoyment of the wine experiences.
With a 4.5/5 overall rating from 314 reviews, this Chianti and Castles Tour is an excellent choice for those seeking a comprehensive and immersive exploration of the Chianti region from Siena.
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Small Group E-Bike Chianti Tour With Farm Lunch From Siena
Travelers seeking an immersive experience in Tuscany’s picturesque Chianti region can embark on a Small Group E-Bike Chianti Tour with Farm Lunch from Siena.
This full-day tour, highly recommended by 93% of past participants, offers an intimate exploration of the area’s scenic landscapes and local culture. Led by knowledgeable guides, groups of up to 8 travelers will ride electric bikes through the Chianti Hills, stopping to visit a restored monastery and enjoy a wine tasting and lunch at a local farm or winery.
The tour includes all necessary equipment, as well as gratuities, making it a convenient and inclusive way to experience the best of Tuscany. While a strong fitness level is required, the e-bikes provide an assisted ride, allowing participants to fully enjoy the breathtaking views of rolling vineyards.
With its 4.8-star rating based on 30 reviews, this tour is an excellent choice for those seeking an unforgettable Chianti adventure.
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From Siena: Brunello Di Montalcino Wine Tour by Minivan
Although situated just a short drive from Siena, the historic town of Montalcino and its renowned Brunello wine hold a captivating allure for oenophiles and adventure-seekers alike.
The Brunello di Montalcino Wine Tour by Minivan offers an immersive experience, guiding visitors through the region’s picturesque landscapes and premier wineries. At £87.84 per person, the 5.5-hour tour limits group sizes to 8, ensuring a personalized and intimate journey.
Participants will embark on a minivan ride to Montalcino, where they’ll enjoy two wine tastings at prestigious local wineries. The tour provides an opportunity to learn about the unique maturation process of Brunello, with its distinctive aging in wood casks.
During the journey, travelers will also have free time to explore Montalcino and capture the essence of the peaceful Tuscan countryside. With an overall rating of 4.1/5 and positive feedback on the knowledgeable guides and scenic views, this tour promises an unforgettable experience for wine enthusiasts.
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Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum
For those seeking an immersive introduction to the captivating city of Siena, the Guided Tour of Siena INCLUDING the Cathedral or Museum provides a comprehensive exploration of the historic landmarks and cultural heritage.
This tour starts at Piazza Salimbeni and concludes at the iconic Piazza del Duomo, allowing visitors to experience Siena’s stunning architecture and rich history. Led by knowledgeable and passionate guides, the tour features engaging storytelling and personal connections to the city.
Participants can expect to learn about Siena’s past while admiring notable sites like the Duomo. However, due to current COVID-19 health restrictions, the cathedral tour isn’t available.
The tour remains an informative and delightful experience, with guides praised for their expertise and humor. While most travelers can participate, the steep streets of Siena can be tiring.
Advance booking is recommended, and visitors should confirm tour details, especially regarding language and timing.
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The Sum Up
Siena offers a range of captivating tours that allow visitors to explore the city’s rich history, stunning architecture, and renowned local cuisine and wines. From guided walks to horseback rides and wine tastings, there’s something to suit every interest. Whether you’re seeking to skip the lines or discover the medieval charm, Siena’s diverse tour options promise an unforgettable experience.