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Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles

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Roma, Italy
Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles

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Free cancellation
Up to 24 hours in advance. Learn more
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Safety measures
icon13 hours  (Approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds


Travel to Tuscany on a day trip from Rome, and discover a region of stunning hilltop towns, farms, and wineries. With a guide, you’ll visit the UNESCO World Heritage Site of Pienza, a beautiful example of a Tuscan hill town. Continue to an organic farm for lunch, sourced straight from the field, then climb the lookout towers at nearby Montalcino. Finish on a high note with a wine tasting at a prestigious winery, then return to Rome. Numbers are limited to just 18 people for a small-group experience. 
  • Day trip to Tuscany from Piazza della Repubblica in Rome
  • Explore the shops of Pienza, a UNESCO-listed hill town
  • Visit an organic working farm in the Val d’Orcia region
  • Satisfy your appetite with lunch, produced by the farm
  • Climb the towers of the castle at Montalcino
  • Sip on several prized wines at a Tuscan wine estate
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Round trip transport from Rome
English-speaking tour leader
Lunch at an organic farm
Wine tastings at Montalcino vineyard
Cheese Tasting
Small groups of max 18 people
Comfortable, air-conditioned transport
Hotel Pick-Up/Drop-Off
CAFFÈ VERGNANO 1882 , Piazzale Flaminio, 5, 6, 00196 Roma RM, Italy

This tour meets in front of Caffè Vergnano 1882 on Piazzale Flaminio n. 5/6, next door to Intesa San Paolo bank. Piazzale Flaminio is a centrally located square (just outside the arches of Piazza del Popolo), served by the Metro A.

7:15 AM
Piazzale Flaminio , Piazzale Flaminio, Roma RM, Italy
Start your tour at 7am at Rome’s Piazza della Repubblica. With a guide, you’ll travel north to Tuscany, a region known for its beautiful hill towns. Stop in one of them, the UNESCO-listed hilltop village of Pienza, and explore its streets and ceramics shops with your guide. Browse delis for gourmet treats to take home, and get an intro to Tuscan specialities, such as pecorino and wild boar, from your guide.

Your next stop is at a family-owned farm in the Val d’Orcia area, which specializes in organic produce. Tour the farm, chat to the cheese maker, then take a seat for lunch. Tuck into a feast of farm-to-fork food, and finish with a tasting of sheep and goat cheese with homemade honey and jam. Local wine is served as you eat and chat with the farm owners — all while soaking up the views. 

With your appetite sated, you’ll continue to the hill town of Montalcino. Use a special admission ticket to head up the lookout tower and take photos from the top.

To end your day, travel onward to an acclaimed winery for a tour of the vineyards and its cellars. Sample a selection of the region’s finest wine, and purchase a bottle to take home, if you like.

Relax on the journey back to Rome, and finish with a drop-off at the start point.
Stop At:  
Your first stop is the UNESCO world heritage hill town of Pienza. Here you’ll wander the beautiful streets, seeing views over the countryside and shopping for food and wine if you wish. Your tour leader will introduce you to traditional Tuscan delicacies like pecorino cheese and wild boar, and point out the best ceramics stores.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
Val d'Orcia
Next we’re heading over to an organic, family-run farm. After a tour of the farm it’s time to sit down for a Tuscan feast of local, seasonal ingredients straight from the fields. The meal is capped off with a full tasting of the farm’s best seasonal food. In between chats with the farm owners you will sip on local wines and enjoy incredible views over the famous Val d’Orcia region.
Duration: 2 hours 
Admission Ticket Free
Stop At:  
Fortezza di Montalcino
After lunch you’ll go to Montalcino, a hill town famous, among many other things, for its beautiful castle. With special, extended access tickets you can climb the lookout towers and gape at the views of the surrounding countryside or snap off a few pictures that will be the envy of all your friends back home.
Duration: 1 hour 
Admission Ticket Included
  • Confirmation will be received at time of booking
  • Unfortunately we are unable to accommodate guests with mobility impairments, wheelchairs or strollers on this tour
  • Tour Only in English
  • Not wheelchair accessible
  • Not recommended for travelers with back problems
  • No heart problems or other serious medical conditions
  • Most travelers can participate
  • This tour/activity will have a maximum of 18 travelers
  • OPERATED BY Walks - Italy, Spain & Greece
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on face masks and attendee health during Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles?
A:The policies on face masks and attendee health are:

  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Face masks provided for travelers
See all safety measures taken by Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles.
What is the policy on sanitization during Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles?
A:The policies on sanitization are:

  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized
See all safety measures taken by Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles.
What is the social distancing policy during Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles?
A:The policy on social distancing is:

  • Social distancing enforced throughout experience
See all safety measures taken by Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles.
What measures are being taken to ensure staff health & safety during Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles?
A:The policies on staff health & safety are:

  • Guides required to regularly wash hands
  • Paid stay-at-home policy for staff with symptoms
See all safety measures taken by Small-Group Tuscany Day Trip from Rome with Hill Towns and Castles.

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Traveler Tips

  • "Tuscany is amazing, and while it was a bit of a drive, it was well worth it." See review
  • "I usually shy away from these package tours, but on a trip to Rome with my mother, she specifically requested a day in Tuscany." See review
  • "Only the good stuff from now on it makes a difference!" See review


48 Reviews
2 stars

Reviews by Viator travelers

Showing 1-10 of 48 reviews
Very pleasant journey to the country side
, Dec 2019
That’s been a pleasure to discover Toscane. We were led by a nice guide who truly loves this region and we’ve been able to meet welcoming people, discover quality products hence being able to buy directly from them was a nice opportunity. Definitely recommends to escape Rome crowd for a day. Special thanks to the driver, very good, considering traffic is not easy.
icon Response from Host , Jan 2020
Hello julienfto, It is such a pleasure to learn that you enjoyed your tour experience with us. We work very hard to select only the best guides available, and cannot express how happy we are to know we have succeeded in making this such a wonderful experience for you! We hope that you will get the opportunity to tour with us again soon! Warmest regards, The Walks Team
I never dipped olive oil on my bread until Tuscany!!!
, Nov 2019
Even though I don't drink I had an amazing time on the tour and my friends enjoyed my wine! I understand why bread is dipped in olive oil. Only the good stuff from now on it makes a difference! Brought several bottles back with me. Our tour guide was great and the entire tour and our tour group was great as well. We all had a ball and when several of us ran into each other in Roma we all yelled family and took another photo together!!!
icon Response from Host , Nov 2019
Hello funtravels53, Thank you for your review! We thrilled to learn that you and your friends had such an amazing time on your tour, and we are even more glad that you will be bringing a little bit of Italy back home with you! We strive to provide our clients with memorable experiences, and it sounds like we achieved this for you, and we are absolutely delighted! We hope that you will get the opportunity to take another walk with us again soon! All the best, The Walks Team
What beautiful countryside!
, Nov 2019
Our tour guide was great. It was such a fun day starting from the pottery shop and the cheese shop that we visited. Our meal that was prepared at the farm was absolutely first class and the hosts at the farm were inviting and welcoming. The vineyard had the most delicious wine. Overall, it was one of our best days in Italy!
icon Response from Host , Nov 2019
Hello Resort18980535902, Thank you for your kind review! It is an absolute pleasure to learn that you had such a fantastic time touring with us. Our number one priority is 100% customer satisfaction, and we are delighted that we achieved this with you! We look forward to sharing more walks with you in the future! Warmest regards, The Walks Team
Drink Up
Michael D
, Nov 2019
Was a real enjoyable time with all the stops we made. Our guide was extremely professional and knowledgable about everything.
Fabulous Day in Tuscany
, Oct 2019
Pavell was our informative and entertaining guide. What a great day in this beautiful country side. We enjoyed excellent wines and a fantastic lunch! Highly recommended!
icon Response from Host , Oct 2019
Thank you so much for your kind recommendation! We're delighted that you enjoyed your trip to the Tuscan countryside with us.
A wonderful day in Tuscany
, Oct 2019
We loved our day trip to Tuscany! We walked around stunningly picturesque Hill Towns, climbed a castle for views of the Tuscan countryside, and tasted the wonderful food and wine of the region. Lunch at the organic farm was amazing. Our guide and driver were excellent and the small group experience was well worth it. This made for a welcome break from the busy city of Rome and was a high point of our trip.
icon Response from Host , Oct 2019
There's no better way to escape the hustle and bustle of a busy city than to take a trip out to the country. We're so glad that you enjoyed your trip to Tuscany from Rome with us!
Amazing day in Tuscany
, Aug 2019
What a wonderful day trip. I think it was our favorite tour of our 9 day trip to Italy. Our guide Andrea made it even more wonderful. His English was amazing and he was funny, knowledgeable and engaging. The air conditioned Mercedes van was comfortable for our group of 16 and we all made friends that day. I was great to get out of the sweltering heat of Rome to go into the beautiful countryside. The views were endless and the small towns enchanting. The lunch at the country estate was the highlight of the day. The food was fresh and amazing and the host was fun and truly enjoyed his work. Wish we could have stayed their all day. They had the best olive oil we had in all of Italy and I wish I would have bought more! I definitely recommend this tour if you want a solid taste of what Tuscany has to offer and you want to get out of the bustle of Rome for day
A wonderful day in the Sun
, Jul 2019
Great well organized tour. Driver and guide were great. Prompt pickup , comfortable ride and knowledgeable guide, Salina. The tastings were great stops and lunch was superb. Long day 7:15 AM to 8:00 PM . Be prepared
Perfect day through Tuscany
, Nov 2018
First of all, our guide Alessandra made this such a fun and memorable day. I couldn't have imagined this day without her knowledge of the region and her passion for Italy and of course, Tuscany and wine. Beautiful countryside, quaint towns filled with lovely people, and the food. OH THE FOOD! AND THE WINE!! One of the most memorable lunches I have ever had and probably will ever have. Thank you for this amazing tour!
Highlight of our Italy experience!
, Oct 2018
This day could not have been better. We had the most helpful and experienced tour guide. The travel by small Mercedes bus (15 max) was comfortable and allowed great views of the countryside. Visits to a small mountain town, a working farm with an amazing lunch, and authenic wine tasting was simply awesome. If you have the opportunity, book this one! I would do it again!

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