
Siena and Chianti Wineries Excursion by Private Luxury Van from Florence
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 12 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Siena and Chianti Wineries Excursion by Private Luxury Van from Florence worth booking?
Siena and Chianti Wineries Excursion by Private Luxury Van from Florence is a 8-hour experience in Florence, Italy, from $700 per person. It scores 48 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.9/5 rating across 12 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 48 / 100
- Rating
- 4.9/5 (12)
- Duration
- 8 hours
- From
- $700 per person
• Experience for your private group. • Explore the art, culture and medieval history of Italy in this private 8-hour Siena and Chianti countryside tour from Florence. • Unforgettable day spent visiting Siena and the Ch
What you get
About this experience
• Experience for your private group. • Explore the art, culture and medieval history of Italy in this private 8-hour Siena and Chianti countryside tour from Florence. • Unforgettable day spent visiting Siena and the Chianti area accompanied by a driver who was born and raised in Tuscany with this 8-hour winery excursion from Florence. Spend your morning exploring the Gothic city of Siena with its famous shell-shaped Piazza del Campo and gorgeous cathedral. In the afternoon you will have the opportunity to visit some of the most famous wineries, or some lesser-known small family businesses, to see their cellars and taste excellent organic wines (own expense). • Upon customer request we can organize lunch in a cellar or organic farm for wine tastings or local foods. Highly recommended experience.
What's included
Included
- Hotel pickup and drop-off
- Free Wi-Fi on board
- Bottled water
- Private luxury van
- Professional English speaking driver
Not included
- Lunch
- Wine tastings
- Gratuities
- Licensed city guide
What you'll see and do
Centro Storico di Siena - World Heritage Site
Siena is known throughout Italy for the quality of its medieval architecture. Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that will allow you to taste local food or buy some gifts!
120 minutes here
Tenuta Casanova
For lovers of food and wine we can organize lunch in an farm to taste wine, balsamic vinegar, extra virgin olive oil paired with local food.
120 minutes here · Admission not included
Stop in a small and organic winery in the Chianti Classico area! Full lunch or Wine tasting.
2 minutes here · Admission not included
Badia a Passignano
Badia a Passignano, a grandiose fortified monastic complex! Surrounded by vineyards that characterize the Tuscan hills and its enchanting landscapes.
Pass by without stopping
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- All sales are final. No refund is available for cancellations.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Chianti Drivers private tours
Know before you go
- Specialized infant seats are available
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Pricing is per vehicle, maximum of 7
Photos






What travelers are saying
Outty’s summary of the themes that recur across 12 traveler reviews. Written by us, not quoted from reviewers.
The guide
8 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
8 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
6 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
12 verified traveler reviews for Siena and Chianti Wineries Excursion by Private Luxury Van from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Would highly recommend driver not winery
Driver was excellent and very informative. His part of the experience was definitely 5 stars. The winery we went to for lunch that was not included was expensive and for the price very little food and wine. We should have asked to go to a more local Spot.
Response from the operator: Hello, lunch is explicitly excluded from the tour you purchased. I'm sorry it was expensive for you...in Chianti, the prices at the wineries are very similar, and lunch, being a technical lunch for the tasting, cannot be like a restaurant but includes the visit, food, and wine. All my best
via Viator
Sienna and Chianti
Marco was professional, knowledgeable and kind. The winery was beautiful, delicious wine & food! Thanks!
Response from the operator: So happy about it
via Viator
Spectacular experience
Sienna was amazing Wish we had a little more time there But the wineries were great too In the heart of the Chianti region Driver was very knowledgeable having grown up in Sienna
Response from the operator: :)
via Viator
Perfect Day in Tuscany
GC took me and my husband out for a day of sightseeing and, wow, we saw sights. The Siena Cathedral is amazingly ornate and the main square where the horse race takes place is fascinating. Then we visited Casa Emma, a beautiful winery where we started with a tour then had a tasting and lunch overlooking the vineyards and olive groves. Our hostess was charming and fun and explained the differences in the wines very clearly and passionately. We started with ravioli, then had roast pork and potatoes, and finished with ice cream drizzled with 100 year old balsamic. It was all delicious. After buying some items for shipping, we moved on to Montefili, another beautiful destination where we tasted on the patio with another expert young lady who was proud to share the story of the vineyard and its wines. GC’s van was large and immaculate. He was friendly and called out points of interest, but was not overly chatty. Just right. He knows these twisty roads like the back of his hand and squeezed around corners and through lanes that we would never try. He took us by a lovely monestery and the town of Greve in Chianti. So we felt we got a good overview of Tuscany in one day and would love to return.
via Tripadvisor
Wonderful time in Sienna, San Gimignano, and Chianti
We had an amazing time on the trip. Michele, our driver, knew the exact places to take us including a wonderful winery in Chianti to have lunch. He also spent a lot of time explaining about the cities and what we would see. We just wish we had more time to spend in each of the cities as it is quick when you have multiple stops in one day. Definitely need to go back and try to spend a day in each city if we can.
via Viator
Good to know
- Duration
- 8 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 4
- Verdict
- Worth a Look
Why this scores 48
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Siena and Chianti Wineries Excursion by Private Luxury Van from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Siena and Chianti Wineries Excursion by Private Luxury Van from Florence cost?
+
Prices start at $700 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Siena and Chianti Wineries Excursion by Private Luxury Van from Florence take?
+
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 Florence is not rushed.
Is Siena and Chianti Wineries Excursion by Private Luxury Van from Florence worth it?
+
It holds an Outty Ranking of 48 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.9/5 across 12 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable family friendly in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Siena and Chianti Wineries Excursion by Private Luxury Van from Florence?
+
No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is Siena and Chianti Wineries Excursion by Private Luxury Van from Florence suitable for kids and families?
+
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 Siena and Chianti Wineries Excursion by Private Luxury Van from Florence?
+
Around 4 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 Florence 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?
+
Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Siena and Chianti Wineries Excursion by Private Luxury Van from Florence start and how do I get there?
+
The exact meeting point and directions are on your voucher once you book, and they sit in central Florence 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 Florence?
+
On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. 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 Florence?
+
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 Florence?
+
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?
+
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.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Siena and Chianti Wineries Excursion by Private Luxury Van from Florence.
Pick your date




