
Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
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Quick answer
Is Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up worth booking?
Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up is a 9-hour experience in Rome, Italy, from $300 per person. It scores 50 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
- 50 / 100
- Rating
- Not yet rated
- Duration
- 9 hours
- From
- $300 per person
Escape the bustling streets of Rome and explore the picturesque Val d’Orcia on this private day trip. With a friendly English-speaking driver, visit the charming towns of Montepulciano, Pienza, and Montalcino, known for
What you get
- Private transportation
About this experience
Escape the bustling streets of Rome and explore the picturesque Val d’Orcia on this private day trip. With a friendly English-speaking driver, visit the charming towns of Montepulciano, Pienza, and Montalcino, known for their stunning landscapes and rich wines. Enjoy the flexibility to customize your itinerary to include a winery visit and tasting, or simply savor the breathtaking views and local cuisine at your own pace. This tour offers a unique glimpse into Tuscan culture, perfect for wine enthusiasts and travellers seeking a personalized experience. - Private transportation in a comfortable Mercedes sedan or minivan - Explore UNESCO-listed Val d’Orcia, stopping in Montepulciano and Montalcino - Customize your itinerary with optional winery visits and lunch - Full-day tour lasting approximately 10 to 11 hours from Rome, with hotel pick-up and drop-off
What's included
Included
- Private transportation
Not included
- Lunch
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.
30 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)
30 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.
30 minutes here · Admission 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
120 minutes here
Fortezza di Montalcino
If you wish, you can enter and visit the very well preserved Medieval castle of Montalcino
30 minutes here · Admission included
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
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
- TOURS FROM PARIS
Know before you go
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
Photos






Good to know
- Duration
- 9 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $300 to $1700
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 50
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Rome.
How much does Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up cost?
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Prices start at $300 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 Wine and Hill Towns Day Trip with Hotel Pick up take?
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Plan for about 9 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 Wine and Hill Towns Day Trip with Hotel Pick up worth it?
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It holds an Outty Ranking of 50 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 Rome, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up?
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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 Wine and Hill Towns Day Trip with Hotel Pick up suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up?
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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 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 9-hour experience runs outdoors or after sunset.
Where does Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up 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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