"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings
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Quick answer
Is "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings worth booking?
"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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
Experience a Day in the Heart of the Chianti Hills with Wine Tasting and Medieval Villages Spend an unforgettable day surrounded by the rolling hills of Chianti, dotted with cypress-lined roads, vineyards, sunflowers, an
What you get
- Private transportation
- Lunch
- Bottled water
- Local expert driver and tour leader
- In-vehicle air conditioning
- All inclusive tour
About this experience
Experience a Day in the Heart of the Chianti Hills with Wine Tasting and Medieval Villages Spend an unforgettable day surrounded by the rolling hills of Chianti, dotted with cypress-lined roads, vineyards, sunflowers, and charming medieval villages. Explore the enchanting village of Castellina in Chianti, savor authentic homemade pasta, and enjoy the finest Chianti wines at two traditional Tuscan wineries. Highlights: • Scenic drive through the iconic Chianti countryside, with olive groves, cypress trees, and vineyards as far as the eye can see. • Stroll through the historic streets of Castellina in Chianti and soak up its medieval charm. • Enjoy a genuine 3-course Tuscan lunch at a traditional farm, including homemade pasta, seasonal dishes, and extra virgin olive oil, paired with 5 local wines. • Stop at a local family-run winery on the way back to taste wine made the traditional way. • Convenient hotel, B&B, or private flat pickup and drop-off included.
What's included
Included
- Private transportation
- Lunch
- Bottled water
- Local expert driver and tour leader
- In-vehicle air conditioning
- All inclusive tour
- Alcoholic beverages
Not included
- Everything not found under the heading inclusions is excluded
What you'll see and do
Strada Statale 222 Chiantigiana
Our driver will pick you up and guide you along the Via Chiantigiana, a picturesque route through the Tuscan countryside starting from the Arezzo area. This scenic road winds past rolling vineyards, olive groves, and iconic cypress trees, showcasing the timeless beauty of Chianti. Along the way, you’ll pass charming medieval villages, rustic stone farmhouses, and historic wineries, surrounded by landscapes that feel like living paintings. The Via Chiantigiana offers a perfect introduction to Tuscany’s rich wine culture and peaceful rural charm.
Pass by without stopping
Castellina In Chianti
After about an hour, you’ll arrive in Castellina in Chianti, a charming town steeped in medieval history. Stroll through its historic center, where artisan shops and traditional wine and cheese boutiques line the streets. Once a strategic site in the battles between Florence and Siena, Castellina is rich in history, with underground vaulted passageways and a medieval fortress that now houses a fascinating museum. As you explore, enjoy breathtaking panoramic views along the scenic country roads. The surrounding landscape is a feast for the senses, with rolling wheat fields, lush vineyards, and cypress-lined curves filling the air with the unmistakable aromas of the Tuscan countryside.
30 minutes here
Badesse
For lunch, we will visit a family-run Tuscan farm, where you’ll experience the true warmth of rural Italy, surrounded by vineyards and rolling hills. Meet the local winemaking family and discover the secrets of traditional Tuscan wine-making. • Enjoy a genuine homemade 3-course meal made with fresh, local ingredients: • Bruschettas, artisanal cold cuts (salami, prosciutto), and pecorino cheeses • Homemade pasta with traditional Tuscan sauces • Paired with a guided tasting of 6 exceptional wines, from crisp whites to Chianti DOCG, Chianti Riserva, and bold Super Tuscans Finish with extra virgin olive oil tastings, savoring the authentic flavors of Tuscany, crafted with care by a family who has nurtured their land and traditions for generations.
120 minutes here
San Donato in Poggio
The final stop will be at a second family-run Chianti winery, a charming estate in the heart of Chianti. Here, wine has been crafted for generations using traditional methods, guided by expert winemakers, resulting in limited but exceptional bottles with a unique character. Enjoy a special guided wine tasting, savoring the rich aromas and flavors of their carefully produced Chianti reds as well as prestigious white wines, each reflecting the expertise and passion of the family. After this delightful stop, we’ll return you to your location—whether it’s your hotel, private flat, or B&B—concluding a perfect day exploring the flavors and beauty of Tuscany.
60 minutes here
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
- 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
- Suitable for all physical fitness levels
- Public transportation options are available nearby
- Infants and small children can ride in a pram or stroller
- All areas and surfaces are wheelchair accessible
- Wheelchair accessible
Photos
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $100 to $260
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Who runs this experience
Operated by Pek Tuscany in Limo, who run 48 experiences we rank across 9 cities, with an average Outty Ranking of 51.1.
See everything Pek Tuscany in Limo runsWhy this scores 60
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Arezzo.
How much does "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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 "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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 "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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 "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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 "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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 "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine 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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