PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings
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September 2026
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Adults
Age 13 and over
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Age 12 and under
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Quick answer
Is PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings worth booking?
PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings is a 8-hour experience in Arezzo, Italy, from $100 per person. It scores 60 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 60 / 100
- Rating
- Not yet rated
- Duration
- 8 hours
- From
- $100 per person
A full day trip into the landscape of the rolling Chianti hills, cypress avenues, medieval villages and tasting of the best wines of our region. In the morning, meet the driver at your hotel or another chosen location. W
What you get
- Private transportation
- Lunch
- Bottled water
- Alcoholic beverages
- In-vehicle air conditioning
About this experience
A full day trip into the landscape of the rolling Chianti hills, cypress avenues, medieval villages and tasting of the best wines of our region. In the morning, meet the driver at your hotel or another chosen location. We'll cross the rolling Tuscan hills, among olive groves, cypresses & vineyards. •Visit the magnificent city of Siena and the historic center. Siena is famous for its stunning architecture and beautiful main square: Piazza del Campo. Siena has a historic center that has been declared a world heritage site by UNESCO. Siena is also known for its legendary Palio horse race which takes place twice a year and attracts hundreds of spectators. •Next move to a real Tuscan farm, to understand the secrets of wine production and enjoy a lunch with homemade pasta and 6 wine tastings. •After lunch, visit the wonderful Medieval Castle of Monteriggioni. •On the way back you will have a second wine tasting in a Chianti winery tasting the King of the wines: The Chianti Black rooster.
What's included
Included
- Private transportation
- Lunch
- Bottled water
- Alcoholic beverages
- In-vehicle air conditioning
Not included
- Everything not found under the heading inclusions is excluded
- Pro guide not included
What you'll see and do
Siena
Our expert driver will pick you up directly from your location (hotel, B&B, or private apartment) for a scenic drive through Tuscany’s charming hills. The first stop is Siena, where you can enjoy a self-guided tour and some free time to explore at your own pace. Siena, the capital of its province, is famed for its stunning architecture and the iconic Piazza del Campo. Its historic city center is a UNESCO World Heritage Site, offering a wealth of cultural and artistic treasures. Siena is also renowned for the Palio, its legendary horse race held twice yearly, which attracts hundreds of spectators from around the world.
90 minutes here
Strada Statale 222 Chiantigiana
After exploring the magnificent city of Siena, we will embark on a scenic journey through one of the most iconic regions of Tuscany. Leaving the medieval center behind, we’ll dive into a picturesque landscape of rolling hills, silvery olive groves, and meticulously cultivated vineyards. The road gently winds through small villages, cultivated fields, and cypress-lined woods, an unmistakable symbol of the Tuscan countryside. We will cross the heart of the Chianti Senese region, renowned for its prestigious wines, passing by stone farmhouses, medieval towers, and rows of vines stretching toward the horizon.
Pass by without stopping
At the Marronaia Winery, guests will enjoy an authentic Tuscan dining experience surrounded by the breathtaking countryside of San Gimignano. The meal consists of three delicious courses, carefully crafted to highlight the region’s culinary traditions and paired with five exceptional wines. The Experience The journey begins with a warm welcome and an introduction to the family-run winery’s history and philosophy. Guests will then be seated in a charming rustic setting, either in the beautifully restored farmhouse or on the terrace overlooking the rolling hills and vineyards. The Wines: Throughout the meal, five carefully selected Tuscan wines will be served, each paired to complement the dishes. Vernaccia, Chianti, Chianti Riserva and Super Tuscan
90 minutes here · Admission included
Monteriggioni
After lunch, we’ll head to the enchanting Monteriggioni Castle. Built by the Sienese between 1213 and 1219, this medieval fortress served as a strategic outpost against the Florentines. Perched atop a hill, Monteriggioni is renowned for its well-preserved defensive walls and 14 majestic towers that dominate the surrounding countryside. Once considered an impregnable stronghold, the castle played a pivotal role in regional conflicts during the Middle Ages. Today, its cobblestone streets, charming squares, and breathtaking views transport visitors back in time, offering a perfect blend of history and beauty.
30 minutes here
Fattoria Lornano
Final Stop: A Traditional Chianti Winery Experience To conclude your unforgettable day in Tuscany, we will visit a renowned winery, such as the Chianti Winery, Lornano Winery, Guidi Winery, or Poggio ai Laghi Winery. Each of these is a quintessential Tuscan estate, steeped in tradition and known for producing exceptional wines over generations. During this visit, you’ll enjoy a second wine tasting, featuring the crown jewel of Tuscan wines: Chianti Classico, proudly marked with the iconic "Gallo Nero" (Black Rooster) seal. This rich and elegant wine, celebrated worldwide, will be accompanied by expert insights into its history, production, and distinctive flavors. After this indulgent tasting, we will return you to your hotel or private apartment, leaving you with unforgettable memories of Tuscany’s wine culture and breathtaking landscapes.
45 minutes here · Admission included
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 travelers per booking
- Operated by
- Pek Tuscany in Limo
Know before you go
- Specialized infant seats are available
- Public transportation options are available nearby
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
- Wheelchair accessible
Photos
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- 1+
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $100 to $250
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 60
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Arezzo.
How much does PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings cost?
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Prices start at $100 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Arezzo usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings take?
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Plan for about 8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Arezzo is not rushed.
Is PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings worth it?
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It holds an Outty Ranking of 60 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Arezzo, and how flexible the cancellation terms are.
Can I cancel or reschedule PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings suitable for kids and families?
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The operator sets a minimum age of 1. Older children generally do well here, and families should factor in the 8-hour running time when deciding.
How far in advance should I book PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Arezzo can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Arezzo and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Arezzo within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Arezzo?
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On Outty we rank every Arezzo experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Tour of the vineyards and tasting of Evo wines and oil in Tuscany, Wine and olive oil tastings with the locals, Cellar Tour & Wine Tasting. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Arezzo?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Arezzo?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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