
Private: Tuscany Day Tour from Rome with Optional Wine Tasting
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September 2026
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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.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 13 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private: Tuscany Day Tour from Rome with Optional Wine Tasting worth booking?
Private: Tuscany Day Tour from Rome with Optional Wine Tasting is a 10-hour experience in Rome, Italy, from $709 per person. It scores 57 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 13 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 57 / 100
- Rating
- 5/5 (13)
- Duration
- 10 hours
- From
- $709 per person
With this private daytrip from Rome you will: - Stop at ancient lovely towns - Drive through the beautiful countryside of Tuscany - Visit a winery and enjoy a wine tasting (optional) - Ride on a comfortable Mercedes (se
What you get
About this experience
With this private daytrip from Rome you will: - Stop at ancient lovely towns - Drive through the beautiful countryside of Tuscany - Visit a winery and enjoy a wine tasting (optional) - Ride on a comfortable Mercedes (sedan or minivan) - Meet the driver at your hotel - Customize the itinerary based on your needs - Have the option of a drop-off in Florence
What's included
Included
- Mercedes sedan/minivan
- Winery visit and wine tasting (optional at additional price)
- Private driver (English speaking)
- The itinerary can be customized based on your preferences
- Hotel pick-up and drop-off
Not included
- Lunch
- Tour Guide
What you'll see and do
Montepulciano
The first stop will be at the town of Montepulciano. Built in the Medieval times, this charming center sits on top of a hill and is well known for the production of vino Nobile di Montepulciano
60 minutes here
Piazza Grande a Montepulciano
Right in the heart of the town of Montepulciano, Piazza Grande is an ancient square with Medieval buildings, little shops, various nice bars and restaurants.
20 minutes here
Monticchiello
After Montepulciano, we will pass by the town of Monticchiello, driving through the beautiful countryside of Tuscany
Pass by without stopping
Historic Centre of the City of Pienza
Next stop will be in the lovely town of Pienza, a jewel of the Renaissance. Here you can stop for lunch in one of the many local restaurants (lunch is not included but we will be happy to make a reservation for you)
80 minutes here
Il Duomo di Pienza
The cathedral of Pienza dominates the beautiful central square. Built around the 14th century, is one of the most important churches of the Renaissance times
30 minutes here
Palazzo Piccolomini
Near the cathedral, the Piccolomini palace is a splendid Renaissance example of Renaissance architecture. Here you may want to visit the lovely gardens, the courtyard and the old stables.
20 minutes here · Admission not included
Montalcino
In the afternoon you will reach the town of Montalcino, the capital of the region that produces Brunello, one of the best and most renowned red wines in the world
70 minutes here
Fortezza di Montalcino
If you wish, you can enter and visit the very well preserved Medieval castle of Montalcino
15 minutes here · Admission not included
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Options you can book
Tuscany Tour + Wine
Tuscany Tour + Wine: Winery visit + Wine tasting Pickup included
Tuscany Tour
Pickup included
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 12 travelers per booking
- Operated by
- Kiss from Italy
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Specialized infant seats are available
- Transportation options are wheelchair accessible
- Suitable for all physical fitness levels
- Please note that a fair amount of walking is required as the town centers are pedestrian only areas
- We recommend wearing comfortable walking shoes
Photos






What travelers are saying
Outty’s summary of the themes that recur across 13 traveler reviews. Written by us, not quoted from reviewers.
The guide
6 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
6 mentionsThe tastings and food stops are a highlight for most reviewers.
Organization
4 mentionsPickup, timing, and logistics are described as running smoothly.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
13 verified traveler reviews for Private: Tuscany Day Tour from Rome with Optional Wine Tasting. Ratings and reviews provided by Viator and Tripadvisor.
Highlight day of my Italian vacation
After a 3 week whirlwind around southern Italy, I was ready for a much needed R & R and I sure got that with "Alex" on my rainy, but beautiful and mystical magical day driving throughout the lovely small towns in and around Tuscany. I honestly have to say it was the best day of my 21 day trip. Alex was very easy to be with and talk to. He gave me much insight into Italy answering many questions which I still had. Communication with "Kiss From Italy" was excellent throughout and I have to say I wish I could do the day all over again. A great highlight of my trip. Thank you.
via Tripadvisor
Highly recommend Tuscany with wine tasting. Request Lorenzo!
White glove, personal experience. Incredibly friendly guide who explained the experience as we went. Fantastic memory we will never forget
via Viator
The Dream Tour in a Dream Destination
I booked this for a family of 10 and they had an AMAZING experience on the tour and I, as the travel agent, had an amazing experience communicating with Kiss from Italy. I am making them my GO TO company for private tours. My clients expect excellence and Kiss from Italy provided excellent service. Don't hesitate - the guides/drivers/experience was perfecto!
via Tripadvisor
Loved it and relaxing. ...
Loved it and relaxing. Wanted to see more wildflowers and instead had to pig out everywhere. I love food.
via Viator
A Wonderful Day in Tuscany
What a wonderful experience. Alessandro picked us up in rome on time in an immaculate and comfortable van. The drive up to Tuscany included stops to take photos of the beautiful countryside. The three planned stops went as planned and I enjoyed the free time to explore. He provided a great recommendation for our lunch. The tour of the winery was top-notch. We had the complete place to ourselves which made for a special tasting experience. I would also point out that the communication from the tour company was outstanding. When I was unable to obtain details prior to the tour, Francesca made sure to contact me with all the information I needed. Again, a wonderful experience.
via Viator
Good to know
- Duration
- 10 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $709 to $1500
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 5
- Verdict
- Worth a Look
Why this scores 57
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private: Tuscany Day Tour from Rome with Optional Wine Tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Rome.
How much does Private: Tuscany Day Tour from Rome with Optional Wine Tasting cost?
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Prices start at $709 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Rome usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private: Tuscany Day Tour from Rome with Optional Wine Tasting take?
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Plan for about 10 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 Rome is not rushed.
Is Private: Tuscany Day Tour from Rome with Optional Wine Tasting worth it?
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It holds an Outty Ranking of 57 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 13 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Rome, and how flexible the cancellation terms are.
Can I cancel or reschedule Private: Tuscany Day Tour from Rome with Optional Wine Tasting?
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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: Tuscany Day Tour from Rome with Optional Wine Tasting suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private: Tuscany Day Tour from Rome with Optional Wine Tasting?
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Around 5 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 Rome 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 Rome and add a light layer if any part of the 10-hour experience runs outdoors or after sunset.
Where does Private: Tuscany Day Tour from Rome with Optional Wine Tasting 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 Rome 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 Rome?
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Rome runs on skip-the-line access. The Colosseum underground, the Vatican before opening, and the catacombs south of the walls all require a licensed operator, and the price gap between the good ones and the rest is smaller than you would expect. We rank by guide credentials, group size and how reliably the promised access actually materialises. On Outty we rank every Rome experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Rome Pasta and Tiramisu Class: Ravioli, Fettuccine & Fine Wine 5*, Pasta Making & Wine Tasting with Dinner in Frascati from Rome, Rome: Pizza & Tiramisu or Gelato Class with Flowing Fine Wine 5*. 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 Rome?
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April, May, September and October. August is hot and half the city is shut. 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 Rome?
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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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