Italy
Walking & Hiking in Idyllic Tuscany and Mystical Umbria
Program No. 3573RJ
Embark on a fun and informative walking exploration of Italy’s rolling hills as you discover timeless villages, famed vineyards, friendly locals and world-class cuisine.
Participant Reviews
Based on 29 Reviews
SHOWING
An excellent trip in every way. Very well managed by our wonderful guide, Andrea. Great mix of activities, sightseeing and walks not to mention great restaurants and food. It felt like I was seeing Tuscany and Umbria "off the beaten track."
— Review left November 14, 2025
If you want a taste of Italy, this is the hiking adventure of a lifetime with the amazing countryside filled with vineyards and olive trees and small towns with cathedrals and historic town squares and all the amazing Italian food and wine and the friendly Italians.
— Review left November 11, 2025
This was my first RS trip but it will not be my last. I expected it to be nice, it was wonderful. Great hikes in lovely country, incredibly charming ancient villages to wander through, enjoyed with a copacetic group of people. And, I cannot imagine a better guide than Andrea. Thanks RS and thank you Andrea.
— Review left November 8, 2025
I thoroughly enjoyed this Road Scholar trip. It allowed me to experience a part of Italy that I had not yet visited. Walking the countryside and visiting some smaller villages is an excellent was to truly experience and county and its culture.
— Review left October 5, 2025
Idyllic Tuscany and Mystical Umbria was everything I had hoped for. Great leadership and guides, well planned and paced. I learned a great deal bout the history of central Italy and made several great friends on the trip that enhanced the overall experience. I highly recommend this adventure.
— Review left October 5, 2025
This program was beyond fantastic! I strongly encourage anyone interested in Tuscany and Umbria who enjoys spirited walking and hiking to sign up for this program!
— Review left October 3, 2025
My husband and I completed our first Road Scholar trip this September (Tuscany and Umbria), and we know it won't be our last! We're not typically "group people," but the program convinced us that this was the way to travel and get the most out of our experience in a country where we don't speak the language. The balance between educational and cultural experiences and being physically active was ideal for us and was expertly managed by our program instructor from start to finish!
— Review left October 2, 2025
This program perfectly blends learning the history of Italy and the hill towns with wonderful hikes/walks through the countryside and forests of Tuscany and Umbria. The food and accommodations enhanced ones understanding of the Italian way of life.
— Review left October 2, 2025
I had a wonderful time on this trip! Our guide, Andrea, was excellent - he is so knowledgeable and friendly, also very organized. We had a group of 17 participants and I enjoyed getting to know all of them. The program was busy with the tour lectures, various events, hiking, etc and I loved all of it. I enjoyed the hiking. When I got tired or wanted a break, it was fine to take the motor coach to the next town instead of hiking there. The Tuscan/Umbrian scenery and Medieval towns and art are so beautiful. Loved learning about olives, grapes (wine!), Medieval paper making, truffle hunting, etc. Accommodations and food was also excellent. Highly recommend this program!
— Review left September 22, 2025
We would highly recommend this trip. The group leader, Andrea Maccherani who is very knowledgeable about the region, did a wonderful job keeping us focused and informed. His friendly and fun approach helped to make all of us feel comfortable from day one. The countryside is just beautiful so the hikes were peaceful and wonderful. All the field trips were well led by friendly local guides and the family owned places we visited were so interesting. And the food and wine were so good everywhere! The best part was we could eat all we wanted because we walked so much. Last but not least, the Hotel San Gregorio and the Agriturismo Camiano Piccolo were wonderful places to stay while in Italy.
We really can not say enough good things about this trip.
Jennifer and Bob
— Review left September 22, 2025
This is a wonderful tour, full of beautiful scenery, fascinating Renaissance history, world class wine and food and lovely accommodations. On top of that, we had a superb group leader, Andreas, who was organized, knowledgeable and just fun to be around! The walking and hiking experience largely depends on the person and the pace of the group. In our case, we had a pretty speedy group and very warm September weather. This made some of the days surprisingly arduous, if (like me ) you prefer a more relaxed pace. That said, there was never any pressure to keep up and Andreas always stayed behind with us at the back of the pack. Our Umbrian guide Sam, was also very attuned to the group and built in sufficient breaks during our walks. Overall, we enjoyed this tour immensely and also the company of the other RS tour members!
— Review left September 21, 2025
I highly recommend this program. It is fun, active and the food/wine are to not be missed.
— Review left May 29, 2025
I was hoping for something special and this far exceeded my hopes and expectations.
Andrea was a charming and informative tour leader, attentive to everyone’s needs. The specialist guides were excellent as was the accommodation and the quality of the meals.
I saw so much, learned a great deal, got plenty (but not an excessive amount) of walking exercise and enjoyed the company of my fellow travellers.
This was my first Road Scholar trip and I hope that it won’t be my last.
Thank you for a wonderful experience.
— Review left May 22, 2025
My husband and I just completed our first Road Scholar program. We thoroughly enjoyed our experience, met some great people and learned alot about the areas of Tuscany and Umbria that we explored. Our group leader was excellent, as well as the various guides during the program. Highly recommend Road Scholar if you are interested in travel and education.
— Review left April 30, 2025
Hiking in Tuscany and Umbria was a great trip!! There was an excellent balance between the hiking, the scenery, the sightseeing, the food and the wine. I found every day fun and exciting. I was there the last 2 weeks of October and the weather was great, only one day of rain. The leader Irene and the guides were excellent!!
I highly recommend this trip
— Review left December 16, 2024
Great Hiking a postcard at every turn
Great Food and Wine at every meal
— Review left November 13, 2024
What a wonderful hiking trip through Tuscany and Umbria. Beautiful landscapes, delicious food, lively, spirited hikes and some new friends. Lots of pasta, delicious cheese, fresh fruit and vegetables, wonderful wine and olive oil. The satisfaction of a spirited hike well done. Leaders and instructors were informative and gracious. Looking forward to at least one more hiking trip in Italy. I am so glad I was able to take this trip.
— Review left November 13, 2024
Beautiful hiking in the Italian countryside, what's not to like? Olive groves, vineyards, medieval villages set on hilltops, wine, pasta, and a challenging walk everyday to justify the pasta!
— Review left November 9, 2024
This program is a good combination of hiking and touring as well as stops at a wine vineyard, olive oil processor and paper maker. Group leader Irene is fun and engaging. She was on top of all our needs--especially including all the dietary allergies. We had several good local guides that enhanced the program. The hiking varies in difficulty but nothing too onerous and essentially everyone was able to keep up. A little too much of small town touring for me as it seemed repetitive after a while, but most participants enjoyed these. A fun and educational program overall.
— Review left November 4, 2024
I always wanted to visit Italy and this trip to Tuscany and Umbria was the perfect way to do it. Andrea, our group leader, was warm and welcoming to each of us. The countryside was beautiful, the food was fantastic and I learned so much about this wonderful country. I would highly recommend this trip.
— Review left October 21, 2024
My wife and I are just back from this really extraordinary hiking trip through lovely parts of Tuscany and Umbria. We were led by Andrea Maccherani, one of the best leaders we've ever encountered. Every day offered a range of exciting activities, with excellent local guides walking us through the history around us. Packing and moving from hotel to hotel can be a drag, but this Road Scholar trip has only one move, from a beautiful Tuscan hotel in Pienza with spacious comfortable rooms, to a lovely small hotel beautifully set in the foothills 10 minutes from Montefalco in Umbria. Meals were delicious with plenty to eat, which was welcome after hours of exploring. I'm still a little jet lagged as I write this (we arrived home late yesterday), but I didn't want to delay posting this review for a hiking trip that I rank as one of the very best we've ever done.
Jon, Easton, Connecticut
— Review left September 26, 2024
The Tuscan hiking tour was a wonderful experience and my first tour on my own with Road Scholar. Everything was well organized and the hotel’s perfect and the food was marvelous. Tour leader Irene was so experienced and professional with a super sense of humor. The countryside spectacular and the small towns we visited were a great glimpse into the past of Italy’s history!
— Review left May 31, 2024
This truly was a spirited adventure and met my expectations and beyond. I will be looking for another Road Scholar trip for next year and highly recommend this one to others. Hiking in the mountains and countryside of Italy with lovely trees and wildflowers as well as olive groves, vineyards and fava beans was a treat! The food was exceptional. The art and the gardens in the medieval towns was a bonus. Watching the dogs hunt for truffles was a real treat. Walking where Saint Francis walked among old growth trees was enchanting.
— Review left May 6, 2024
This program was fantastic! If you want an inside look into Tuscany and Umbria, don’t hesitate to enroll in this program!
— Review left April 25, 2024
This tour was wonderful. The charm of Tuscany & Umbria, variety of experiences, balance of structured and free time, moderate level of physical challenge with provisions to opt-out, great accommodations, skilled guides, and small group all came together for a really great time.
— Review left October 29, 2023
Great hiking, great food, great wine, and great people to be with… 9 new friends I hope to see again. Best Road Scholar trip I’ve been on (out of four). Physical description is accurate…2 of the hikes were challenging (I’m used to 3-5 miles, but on level ground) but we all adjusted/took our time. Walking poles came in handy at times. 5 stars
— Review left June 12, 2023
We had a great experience hiking through Tuscany & Umbria. Our guide Irene was very professional and personable as were the guides who led us on our hikes. No hike was too difficult and our guides shared lots of historical information and pointed out all the different flora & fauna as the region and terrain changed. We saw a wide variety of things over the course of our time including, wine making/tasting, an olive oil mill, paper making, truffle hunting, and more bell towers and churches I thought existed. They varied in their beauty from simple to over-the-top ornate. An awesome adventure!
— Review left October 26, 2019
The views, the food, the fellow travelers, all delightful. Andrea was so warm and kind. A little rain and cool weather did not detract from the trip at all. The walks were just right and enabled us to enjoy the food and wine without guilt!
— Review left June 12, 2019
Small group, beautiful country hikes, wonderful food. I selected the program because of the description of included activities, and program was as described. Go hike Tuscany and Umbria!
— Review left May 25, 2019