"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 Siena, Italy, from $285 per person. It scores 55 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
- 55 / 100
- Rating
- Not yet rated
- Duration
- 8 hours
- From
- $285 per person
A full day trip traveling through the rolling hills of Chianti, among avenues of cypress trees, medieval villages, fields of sunflowers and legends. Tasting of the best Chianti wines with a delicious lunch in a family-run farm. This is the best private tour for couples, families or small groups of friends: Itinerary: • In the morning meeting with the driver at your hotel or another place of your choice (B&B or private apartment) • We will cross the rolling hills of Chianti, among olive groves, cypresses and vineyards. • We will visit the magnificent Towers of San Gimignano and the historic center. • For lunch we will move to a real Tuscan farm, to understand the secrets of wine production and enjoy a lunch with typical Tuscan foods and 6 tastings of local wines. • After lunch we will visit the invincible Monteriggioni Castle • On the way back we will have a second wine tasting at a local winery, which produces its Chianti Classico wine following the old way. Check out "What to Expect"
What you get
About this experience
A full day trip traveling through the rolling hills of Chianti, among avenues of cypress trees, medieval villages, fields of sunflowers and legends. Tasting of the best Chianti wines with a delicious lunch in a family-run farm. This is the best private tour for couples, families or small groups of friends: Itinerary: • In the morning meeting with the driver at your hotel or another place of your choice (B&B or private apartment) • We will cross the rolling hills of Chianti, among olive groves, cypresses and vineyards. • We will visit the magnificent Towers of San Gimignano and the historic center. • For lunch we will move to a real Tuscan farm, to understand the secrets of wine production and enjoy a lunch with typical Tuscan foods and 6 tastings of local wines. • After lunch we will visit the invincible Monteriggioni Castle • On the way back we will have a second wine tasting at a local winery, which produces its Chianti Classico wine following the old way. Check out "What to Expect"
What's included
Included
- Local expert driver
- Private transportation
- Bottled water
- In-vehicle air conditioning
- Lunch
- Alcoholic beverages
Not included
- Everything not found under the heading inclusions is excluded
What you'll see and do
San Gimignano
Our driver will pick you up directly from your location and take you through the rolling hills of Tuscany to San Gimignano, where you’ll enjoy free time for a self-guided visit. Known as the “Town of Beautiful Towers”, San Gimignano is a perfectly preserved medieval village and a true open-air museum. Once home to over 70 towers, today it offers breathtaking views, artisan shops, and local specialties such as Vernaccia di San Gimignano wine, saffron, and Prosciutto d’Oro. Don’t miss a stop in the main square to taste the world-famous gelato at Gelateria Dondoli, or climb one of the towers for stunning panoramic views and a touch of local legend.
60 minutes here
Strada Statale 222 Chiantigiana
Later, we’ll drive along one of the most beautiful Wine Roads in Tuscany, right through the heart of the Chianti region, whose symbol is the famous Black Rooster. According to legend, after years of conflict, Florence and Siena agreed to define their borders by sending two knights—one from each city—who would depart at sunrise when the rooster crowed. The new border would be set where the knights met. The Sienese chose a white rooster, while the Florentines chose a black one. The Florentines, however, kept their rooster in the dark without food, so on the chosen day it crowed in the middle of the night. Their knight left early and rode much farther, reaching a point just 12 km from Siena. This clever trick is said to explain why the border between Florence and Siena is not halfway between the two cities—and why the Black Rooster remains the enduring symbol of Chianti.
Pass by without stopping
Podere La Marronaia- Le Colonne Biodynamic Winery & Farm
For lunch, we’ll visit a charming family-run organic farm for an authentic Tuscan experience, combining local flavors with expert wine pairings. Enjoy a genuine meal while discovering the secrets of Tuscan cuisine, winemaking, and olive oil production. Lunch includes: • Classic Tuscan dishes: bruschetta, homemade pasta , cured meats, pecorino cheese, dessert, and more • Wine tasting: Chianti, Chianti Riserva, Sangiovese, Vernaccia • Olive oil and balsamic tasting, including pepper olive oil and truffle oil A full sensory experience that perfectly pairs Tuscan food and wine, letting you taste, learn, and savor the region’s finest flavors.
90 minutes here · Admission included
Monteriggioni
After lunch, we’ll head to Monteriggioni for a self-guided visit. Founded by the Sienese in 1213 as a fortress against Florence, Monteriggioni was once considered impregnable. The Florentines could never conquer it through force alone—they succeeded only through deception. By bribing the Sienese captain Giovanni Zeti, they breached the walls, capturing the fortress, sacking the town, and taking many prisoners. Siena was forced to surrender to Florentine rule. According to local legend, on full moon nights, the sounds of trampling hooves and ghostly moans can still be heard. They are said to be the restless spirit of Captain Zeti, unable to find peace after his betrayal. Monteriggioni today is a perfectly preserved medieval village, offering a step back in time and stunning views from its walls.
30 minutes here
Badesse
Our final stop will be at a small, family-run Chianti winery, where wine has been produced genuinely for generations. Here, you’ll enjoy a second tasting featuring Classic Chianti, Chianti Riserva, other Tuscan wines, and the prestigious Super Tuscan, along with extra virgin olive oil. Chianti wines are made the traditional way—small quantities, exceptional flavor, and centuries of expertise passed down through generations. After the tasting, we’ll return you to your location, concluding a full day of authentic Tuscan experiences.n.
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, 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
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- 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 55
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 Siena.
How much does "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings cost?
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Prices start at $285 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena 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 Siena 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 55 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 Siena, 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 Siena 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 Siena 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 Siena 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 Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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 Siena?
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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 Siena?
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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.
What is included in "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings?
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Included: Local expert driver; Private transportation; Bottled water; In-vehicle air conditioning; and Lunch. Not included: Everything not found under the heading inclusions is excluded. Always check the voucher for the final list before you travel.
Does "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings include hotel pickup?
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Yes, pickup is offered for every traveler from 107 listed pickup locations in and around Siena. You can also enter a custom pickup address when booking.
What languages is "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings offered in?
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It is offered in English, Italian, French and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings wheelchair or stroller accessible?
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The operator notes: Specialized infant seats are available; Infants and small children can ride in a pram or stroller; and Wheelchair accessible. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to "Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
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