Get the most out of Siena with guided tours exploring Tuscany’s finest offerings. The city’s medieval charm comes alive through expert-led excursions focusing on history, wine, and food. Walking tours through the historic center hit all the right spots, while wine tours into the countryside showcase prestigious Brunello and Chianti vineyards. The best small-group experiences combine village hopping with winery visits and authentic Tuscan lunches.
We especially love the half-day walking tours that cover Siena’s must-see landmarks – they’re perfect for first-timers. For food lovers, the cooking classes paired with market visits offer hands-on culture. Private wine tours stand out for their flexibility and personal attention.
Check out these tested-and-approved tours for your Siena adventure:
Good To Know
- Comprehensive wine tours and tasting experiences, including visits to historic wineries and tastings of renowned wines like Brunello di Montalcino and Chianti.
- Immersive culinary experiences, such as food and wine tours, traditional Tuscan lunches, and gelato tastings, offering a delectable exploration of local specialties.
- Scenic tours highlighting the stunning Val d’Orcia landscape, picturesque medieval villages, and the iconic Chianti hills, providing breathtaking views of the Tuscan countryside.
- Cultural and historical tours, including walking tours of Siena’s UNESCO-listed sites, personalized explorations of hidden gems, and insights into the city’s rich heritage.
- Highly-rated tours with excellent customer feedback, knowledgeable guides, and customizable experiences tailored to individual interests and accessibility needs.
Wine Tour With Wine Tasting in Siena
Although Siena is renowned for its well-preserved medieval architecture, the city’s true passion lies in its exceptional wine production.
Visitors can experience this passion firsthand through the Wine Tour with Wine Tasting in Siena. This immersive tour takes guests to an organic vineyard in the heart of Tuscany, where they’ll enjoy a guided visit and a sensorial tasting of at least four organic wines typical of the area.
The small group size ensures personalized attention from the knowledgeable guides, who share insights into the region’s winemaking traditions and sustainable farming practices.
Guests also have the opportunity to explore a historical wine cellar and indulge in a light Tuscan lunch featuring fresh, seasonal ingredients.
With perfect reviews, this tour offers a comprehensive and enjoyable experience for wine enthusiasts seeking to explore the rich wine heritage of Siena.
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Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch
What better way to take in Tuscany’s renowned Brunello wines than through the Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch? This daylong tour offers an intimate glimpse into the region’s winemaking heritage.
Travelers visit two historic wineries, partake in tastings, and savor a pairing lunch at a renowned estate. With a maximum of 8 participants, the experience promises personalized attention from knowledgeable guides.
Pickup is available from Siena, Chianti, and Florence, ensuring convenience. The tour includes all transportation, bottled water, and gratuities.
Highlights include exploring the charming town of Montalcino and admiring the stunning Val d’Orcia landscape. Customer reviews praise the excellent wines, informative hosts, and delectable local cuisine.
While some found the price point high, the majority considered it a worthwhile investment for an immersive Brunello journey. Wheelchair accessibility and infant seating make this tour inclusive.
For wine enthusiasts seeking an intimate Tuscan experience, this tour delivers an exceptional opportunity.
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Vespa Tour With Lunch&Chianti Winery From Siena
Why not explore the picturesque Chianti hills of Tuscany on a Vespa scooter? This full-day tour from Siena promises an adventure through the countryside, guided by a professional.
You’ll visit a Chianti winery for a tour, tasting, and light lunch, while also taking in views of Monteriggioni and ancient villages along the way.
The tour includes all necessary equipment, such as helmets and fuel, as well as transportation to and from the meeting point, if desired.
However, participants must have a valid international driver’s license and prior scooter experience, as this tour isn’t suitable for novice riders.
Safety is a concern, with some feedback noting inadequate training and guidance. Those with serious health conditions or who are pregnant should also avoid this activity.
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Walking Tour of Siena With Food & Chianti Wine
Offering an immersive exploration of Siena’s rich history and local culinary delights, this walking tour takes visitors on a captivating journey through the city’s UNESCO-listed Piazza del Campo and other architectural gems.
Led by licensed guides, the small-group experience is limited to 10-12 people, ensuring personalized attention. Participants will savor Chianti Classico wine, Tuscan salami, prosciutto, and pecorino cheese, as well as homemade bread, jam, and pasta.
The tour also includes an awarded gelato tasting, providing a delightful respite. With 88 reviews and a 97% recommendation rate, this tour has earned a Badge of Excellence.
Priced at €75.05 per person, it’s an excellent value considering the wealth of inclusions, from the Duomo di Siena entry ticket to the knowledgeable guides who share insider stories and photography tips.
Whether you’re a history buff or a food enthusiast, this walking tour promises an unforgettable experience in the heart of Siena.
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Chianti and Castle Small Group Tour From Siena With Wine Tasting
Departing from the heart of Siena, this small-group tour takes visitors on an immersive exploration of the renowned Chianti wine region.
With a 4.4-star rating from 141 reviews, the tour includes transport in an air-conditioned minivan or minibus, visits to two popular wineries, and the opportunity to sample 7 types of wines, olive oil, and balsamic vinegar.
Participants will also enjoy free time in the picturesque medieval village of Monteriggioni, where they can explore the historic castle at their own expense.
The tour further includes a tasting of local products such as bread and salami. While hotel pickup is available for an additional fee, the meeting point is at the Hotel Minerva in Siena.
With a maximum of 20 travelers per tour, this experience caters to most guests, though climbing stairs is required.
Feedback highlights the knowledgeable guides, scenic drives, and enjoyable wine tastings, though some suggestions for improvement include better communication and adjusting the castle visit timing in winter.
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Savor Siena Food and Wine Tour
This 4.9-star Savor Siena Food and Wine Tour allows visitors to enjoy the traditional cuisine of Tuscany.
Over 14 travelers, guests embark on a culinary journey, sampling local specialties like pecorino sheep cheese, ciccino focaccia, and panforte cake.
The tour also offers tastings of three renowned regional wines: a historic white, Chianti Classico, and Vin Santo dessert wine.
With a 100% recommendation rate from previous travelers, this tour boasts a Badge of Excellence.
Though not wheelchair accessible, the experience is stroller-friendly and near public transportation.
While some guests desired more historical context during the Siena walking portion, reviewers consistently praised the knowledgeable and engaging guides, Elio and Ambra.
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Full-Day 2 Wineries Tour in Montepulciano With Tasting and Lunch
For those seeking a more immersive exploration of Tuscany’s renowned wine country, the Full-Day 2 Wineries Tour in Montepulciano offers an exceptional opportunity. Boasting a 95% recommendation rate from 73 travelers, this small-group tour includes hotel pick-up and drop-off, allowing guests to fully enjoy the region’s wine culture.
During the tour, you will visit two local wineries, sample a variety of Tuscan wines, and enjoy a traditional lunch featuring regional specialties. The knowledgeable English-speaking guide will provide insights into the winemaking process, introducing guests to the passionate producers. The scenic views of the Tuscan countryside further enhance the overall experience.
With a maximum group size of 8 travelers, the tour ensures a personalized and intimate exploration of Montepulciano’s wine scene. Wheelchair accessibility and infant seats make it suitable for a range of travelers.
While some have noted a desire for more time in Montepulciano, the tour’s overall ratings and positive reviews suggest it’s a must-do for wine enthusiasts visiting the Siena area.
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Pienza, Val Dorcia, Montalcino Wine and Pecorino Cheese PRIVATE TOUR From SIENA
Set out on a captivating private tour that immerses you in the enchanting landscapes and renowned delicacies of southern Tuscany.
Explore Pienza, Val d’Orcia, and Montalcino, accompanied by a knowledgeable guide in a luxury Mercedes vehicle. Sample the region’s famous Brunello di Montalcino wine and savor a delicious lunch at a local farm.
The tour includes hotel pickup and drop-off, Wi-Fi, air conditioning, and bottled water. Entrance fees, wine tasting fees, and a picnic lunch are all covered, ensuring a seamless and immersive experience.
With a minimum of 2 and a maximum of 8 people per booking, this tour offers an intimate and personalized adventure.
Traveler reviews praise the tour’s stunning scenery, delectable local cuisine, and the expertise of the guides.
Whether you’re a wine enthusiast or simply seeking an authentic Tuscan experience, this private tour is a must-do, with a 100% traveler recommendation and an average rating of 5.0 stars.
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Half-Day Brunello Di Montalcino Wine Tour From Siena
Though compact in duration, the Half-Day Brunello Di Montalcino Wine Tour From Siena offers an immersive exploration of the renowned Brunello di Montalcino wine region.
This small-group tour, rated 4.1 stars from 64 reviews, takes guests on an afternoon adventure to Montalcino, home of the prestigious Brunello di Montalcino wine.
Travelers will visit two local wineries, where they’ll enjoy tastings accompanied by cured meats, cheeses, and bread.
Along the way, they’ll learn about the winemaking traditions and the secrets behind the Sangiovese grape. The tour also provides scenic views of the picturesque Tuscan countryside.
Transportation is offered in an air-conditioned minivan or minibus, with hotel pickup available for an additional fee.
While customer feedback highlights positive experiences with the tour’s drivers and routes, some guests have reported issues with the food variety, organization, and tour duration.
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Tuscany Hiking Tour From Siena Including Wine Tasting
Travelers seeking an immersive Tuscan experience can embark on the Tuscany Hiking Tour from Siena, which includes a wine tasting. This highly-rated tour boasts a 98% recommendation from travelers and a Badge of Excellence.
The scenic hike along the historic Via Francigena, a pilgrimage route from Canterbury to Rome, allows participants to explore the picturesque Tuscan countryside, vineyards, and ancient villages. Led by knowledgeable guides, hikers will learn about the route’s rich history.
The tour culminates with a wine tasting in Monteriggioni, where visitors can sample 3-4 local organic wines. Travelers can also explore the medieval town, enjoy lunch, or investigate the historic walls.
While the tour isn’t wheelchair accessible, it’s suitable for those with a moderate fitness level. With a maximum group size of 16, the experience promises a personalized touch.
Reviewers consistently praise the knowledgeable guides and stunning landscapes, making this tour a memorable Tuscan adventure.
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Private Tour: Secret Siena Walking Tour
The Private Tour: Secret Siena Walking Tour offers travelers a personalized journey through the hidden gems and older quarters of central Siena.
With a highly-rated local guide, guests embark on a private walking exploration, departing from the iconic Piazza del Campo. The tour highlights architectural and cultural treasures, including the Church of the Madonna di Provenzano and Basilica di Santa Maria dei Servi, while uncovering the history behind the city’s 17 contrades and the renowned Palio horse race.
Travelers can expect a moderate level of physical activity, with the tour lasting approximately 2-3 hours. Accessible by public transportation and suitable for most fitness levels, this experience provides an intimate look at Siena’s vibrant past and present.
Travelers praise the knowledgeable guides, who customize the itinerary to suit individual interests, offering unique photo opportunities and insider perspectives on the city’s artistic and culinary heritage.
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Discover the Medieval Charm of Siena on a Private Walking Tour
Enjoy the captivating medieval charm of Siena during this private walking tour.
Led by a licensed local guide, you’ll explore the city’s historic old town, including the iconic Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena.
For a deeper dive, you can also opt to visit the Siena Cathedral and admire its stunning artworks by renowned masters like Michelangelo, Donatello, and Bernini.
Throughout the 2-3 hour experience, your guide will share in-depth knowledge of Siena’s rich history and architecture, as well as insights into the city’s vibrant local culture and traditions, including the famous Palio horse race.
With overwhelmingly positive reviews and a 94% traveler recommendation, this tour promises an enriching and memorable exploration of Siena’s medieval allure.
Suitable for most travelers, the tour offers accessibility for wheelchair users and stroller-pushers, with a meeting point near public transportation.
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Private Tour to the Gothic Siena
Why not explore the Gothic splendor of Siena on a private tour? With a 5.0 overall rating from 15 reviews and 100% traveler recommendation, this private tour offers an intimate look into the medieval city.
The tour starts at Piazza San Domenico and ends at the iconic Piazza del Campo, allowing you to experience Siena’s architectural gems up close. For groups over 7, whispers are included to ensure you don’t miss a word from your guide.
Though museum and cathedral tickets aren’t part of the tour rate, the experience itself is worth the investment. Wheelchair and stroller access, as well as proximity to public transportation, make this tour accessible to most travelers.
However, it’s not recommended for those with back problems. As a private tour, you and your group will be the only participants, ensuring a personalized and immersive exploration of Gothic Siena.
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First Time Siena Medieval Tuscany Private Half Day Tour
Designed to provide an intimate exploration of Siena’s medieval wonders, the First Time Siena Medieval Tuscany Private Half Day Tour offers an immersive experience for first-time visitors.
This 5-star rated, half-day walking tour takes guests through the city’s iconic landmarks, including the Piazza del Campo, Siena Cathedral, and Basilica di San Domenico.
With a maximum group size of eight, the tour provides a personalized and flexible experience, allowing the certified private guide to tailor the itinerary to fit individual needs.
Travelers can expect to learn about Siena’s rich history and architecture, with the guide offering insightful commentary throughout the journey.
While entrance fees to museums and churches aren’t included, the tour’s accessibility features, including wheelchair and stroller access, make it suitable for a wide range of participants.
With a convenient meeting point and optional hotel pickup, the tour ensures a seamless experience from start to finish.
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Montalcino Castle and Vineyards Tour With Tasting
Visitors to Siena can embark on a captivating Montalcino Castle and Vineyards Tour, which offers an immersive experience at the historic Castello Tricerchi estate.
The 1.5-hour tour takes guests through the 15th-century castle, exploring 600 years of history, including the chapel, vineyards, and medieval cellars. During the intimate experience, which accommodates a maximum of 15 travelers, knowledgeable guides provide insights into the production of the renowned Brunello di Montalcino wine.
The tasting experience includes samples of Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP, paired with local snacks.
While most guests praise the beautiful property, wines, and guides, some have noted that the tours can feel rushed or that the guides lack detailed historical knowledge.
The Montalcino Castle and Vineyards Tour offers a unique opportunity to explore the rich winemaking traditions of the region, starting from $36.75 per person.
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Discover Siena With Its Cathedral Guided Tour
What better way to explore the historic city of Siena than with a guided tour of its magnificent Cathedral? The Siena Guided Tour with Cathedral and Optional Crypt & Museum offers visitors a deep dive into the city’s rich history and architectural wonders.
This 2-3 hour walking tour takes small groups of no more than 12 people through Siena’s top sights, including Piazza San Domenico, Torre del Mangia, and the iconic Siena Cathedral. Guests enjoy courtesy skip-the-line admission and the option to extend the tour by visiting the Crypt and Museum with an OPA SI Pass.
Led by expert local guides, the tour provides fascinating insights into Siena’s culture and the famous Palio horse race. While access to the unfinished façade and floor mosaics may be limited during certain dates, the overall experience is praised for its personalized nature and guides’ passion and knowledge.
With convenient meeting and end points, and accessibility for wheelchair users, this tour is an excellent way to discover the beauty and history of Siena.
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Private Guided Tour of Siena With a Licensed Local Tour Guide
For those seeking a more personalized exploration of Siena, the Private Guided Tour of Siena With a Licensed Local Tour Guide offers an excellent opportunity. This walking tour is highly recommended by 100% of travelers based on 13 reviews, inviting visitors to discover one of Italy’s most intact medieval towns.
The flexible itinerary allows you to set your own pace as you explore Siena’s highlights, including the Duomo, Piazza del Campo, Churches of St. Dominic and St. Catherine, and the town’s charming narrow lanes.
Along the way, your knowledgeable guide will provide commentary on Siena’s rich history and culture, including the significance of the Palio. The tour also includes possible entrance fees, ensuring a seamless experience.
While the tour isn’t wheelchair accessible, it’s stroller-friendly and accessible to those with moderate physical fitness.
Travelers praise the guide’s charm, informative nature, and attentive service, consistently rating the experience 5 stars across all reviews.
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From Siena: Pienza and Montepulciano Wine Tour
Departing from Siena, the From Siena: Pienza and Montepulciano Wine Tour offers a full-day exploration of two enchanting Tuscan towns renowned for their historic charm and exceptional wines.
With a 3.9-star rating from 94 reviews, this tour transports guests by air-conditioned coach or minivan, accompanied by expert multilingual escorts. The highlight of the experience is the opportunity to savor Chianti and Nobile di Montepulciano wines, complemented by delectable snacks.
Visitors can freely explore the UNESCO-listed town of Pienza, known for its pecorino cheese, and the picturesque Montepulciano, with its wine cellar visits and tastings. While the tour involves moderate walking, it’s not wheelchair accessible. The maximum group size is 50 travelers.
Positive reviews praise the beautiful scenery, knowledgeable guides, and balanced itinerary, though some guests have raised concerns about transportation, wine tastings, and tour confirmations.
Priced from $99.74 per person, the tour offers a reservation option with “Pay Later” flexibility.
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Vintage Fiat 500 Tour From Siena: Tuscan Hills and Winery Lunch
Offering a unique exploration of the Chianti region, the Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch transports participants through the scenic countryside in a classic Italian car.
Rated 4.4/5 based on 51 reviews, this small-group tour (limited to 10 people) allows visitors to drive vintage Fiat 500s and discover the charming medieval village of Monteriggioni before enjoying a 3-course winery lunch.
The tour includes hotel pickup, a scenic drive through the Chianti hills, and a visit to the Poggio Amorelli winery for a guided tour and wine tasting.
The sample menu features regional specialties like bruschetta, pasta, and cantuccini with Vin Santo.
While most travelers praised the beautiful landscapes and engaging experiences, some noted issues with tour guide communication and tour cancellations.
The Vintage Fiat 500 Tour offers a unique opportunity to explore Tuscany’s picturesque countryside behind the wheel of an iconic Italian classic car.
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Afternoon Semi Private Chianti Tour From Siena
Travelers seeking a comprehensive exploration of Tuscany’s renowned Chianti region can embark on the Afternoon Semi Private Chianti Tour From Siena. This VIP experience includes visits to Chianti, Montalcino, and Pienza, along with a delectable lunch.
With a maximum of 6 participants, the small-group format ensures a more personalized and flexible experience compared to larger tours.
The tour includes a history lesson on the Chianti region, a visit to the medieval castle in Montalcino, and a stop at a family-owned winery. Guests can savor four Chianti Classico wines, accompanied by Pecorino cheese, bruschetta, salami, and olive oil.
The tour also grants access to a historical cellar and a medieval cave.
Highly rated with a 97% traveler recommendation, this tour provides an immersive, high-quality experience, as evidenced by the positive reviews praising the knowledgeable guides, enjoyable wine tastings, and beautiful scenery.
Priced at $198.49 per person, the tour offers excellent value and the convenience of free cancellation up to 24 hours in advance.
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Siena Tour and Exclusive Window on Piazza Del Campo
What better way to take in Siena’s artistic and architectural wonders than the captivating Siena Tour and Exclusive Window on Piazza Del Campo? This private 2-hour tour, led by a local expert, offers an exclusive experience with a 4.8-star rating from 40 reviews.
95% of travelers recommend the tour, which includes visits to Palazzo Scotti and its windows overlooking the iconic Piazza del Campo. Guests will enjoy snacks and soft drinks at a stunning location while taking in the city’s beauty.
With wheelchair and stroller accessibility, and a moderate fitness level required, the tour caters to diverse travelers. Highlights include skip-the-line access to Siena Cathedral, where entrance tickets are available from 5 euros.
Praised for their knowledge and accommodating nature, the guides provide personal and memorable experiences, especially for families and small groups.
With free cancellation up to 24 hours prior and a lowest price guarantee, this tour is a must-do for those seeking an immersive and exclusive Siena experience.
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Siena Food Tour – Do Eat Better Experience
What better way to savor the essence of Siena’s culinary heritage than the Siena Food Tour – Do Eat Better Experience? This highly-rated tour, with a 98% recommendation from past travelers, offers an immersive exploration of the city’s traditional cuisine.
Led by knowledgeable local guides, the small-group experience (maximum 12 participants) visits artisan food shops, market stands, and landmark eateries, showcasing a variety of regional specialties. Participants can sample delectable charcuterie, handmade pici pasta, the famous ricciarelli cookies, and more, all while learning about the rich culinary history and culture of Siena.
The tour includes a full lunch, coffee/tea, snacks, and even an alcoholic beverage for those 18 and older. With round-trip transportation and a convenient meeting point, this tour provides a hassle-free way to explore Siena’s flavors.
Consistently praised for its knowledgeable guides, relaxed pace, and delicious offerings, the Siena Food Tour – Do Eat Better Experience is a must for any foodie visiting this enchanting Italian city.
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Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour
For those seeking to enjoy Tuscany’s renowned cheese and wine, the Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour is a must-consider experience.
This private tour from Siena takes guests on a scenic journey through the UNESCO-listed Val d’Orcia region, showcasing the area’s acclaimed cheese and wine. Travelers will visit an organic dairy farm for a cheese tasting, then head to a prestigious Brunello winery in Montalcino for a cellar tour and tastings.
The personalized experience includes a knowledgeable, passionate guide and all transportation, making it a hassle-free way to explore this culinary and cultural gem. With a 100% recommendation rate from previous guests, the tour offers excellent value at $734.94 per group of up to 6 people.
Whether you’re a foodie, wine lover, or simply seeking an authentic Tuscan adventure, this tour delivers a rich, immersive experience in a stunning UNESCO World Heritage setting.
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Cooking Class in a Historical Villa in Siena Provence With Tour
Travelers seeking an immersive culinary experience in Siena, Italy will find the Cooking Class in a Historical Villa in Siena Provence With Tour to be a captivating offering.
This 97% traveler-recommended class takes place in a small-group setting, with a maximum of 14 participants, at a historical villa in Siena. Participants will learn to prepare authentic Italian dishes, including homemade ravioli, spaghetti, and tiramisu, under the guidance of experienced instructors.
The class also includes a wine tasting session featuring local wines. The hands-on experience allows guests to master the art of pasta making from scratch. The menu includes tagliatelle with ragout, ravioli with Pienza cheese and vegetables, and customizable spaghetti alla chitarra.
Bottled water and lunch are provided, and the location is about 50 minutes from Siena. With free cancellation up to 24 hours prior and accessibility for strollers and wheelchairs, this cooking class is a well-reviewed highlight for many travelers to the Siena region.
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Exciting ATV Tour in the Tuscan Countryside
This exciting ATV tour in the Tuscan countryside offers travelers a chance to discover the UNESCO World Heritage Site of the Crete Senesi area, spanning from the Chianti region to the Val d’Orcia.
The small-group experience provides personalized attention, with a maximum of 12 participants. Before the tour, travelers receive a briefing and test drive to ensure they’re comfortable handling the ATVs.
Throughout the excursion, a guide is available to assist and answer questions.
The tour highlights the stunning Tuscan landscape, and 100% of travelers recommend the experience. Reviews praise the amazing views, friendly guides, and unique adventure.
While the tour is more of a leisurely cruise on dirt roads than a trail-style adventure, guests enjoy the adaptability of the operators, who provide coffee, wine, and snacks.
With a moderate fitness level required, this ATV tour is an excellent way to explore the Tuscan countryside in a fun and memorable way.
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The Sum Up
Siena offers a diverse range of tours that cater to various interests. From wine tastings and Vespa rides to cooking classes and ATV adventures, visitors can enjoy the region’s rich cultural and culinary heritage. Whether seeking a leisurely exploration or an adrenaline-fueled experience, Siena has something to suit every traveler’s preferences. These tours provide a unique opportunity to discover the best of what this enchanting city and its surrounding Tuscan countryside have to offer.