Tuscany Tours in May 2026

A great trip, well worth doing. The first day is relatively hard but after that most days were very manageable of around 4 to 5 hours. In the most part the hotels were very conveniently located. The bag pick up and drop off worked perfectly and were waiting at each of our daily destinations without fail. The scenery was magnificent. Tuscany was great and the small villages that you passed through were picture postcard. Loved it.

We loved our walk through the Tuscan hills and gorgeous old towns. It was great to have our bags ready at each hotel and to not have to worry about where we were going to stay.

This is a beautiful, well-marked, varied route, and we were lucky to have near-perfect weather in early May. The trails were not challenging per se, but they were long--generally, we found our fitness watches clocked them in at somewhat more than the posted mileage--and often along high ridges with great views, but exposed to sun and wind. At the end of your long day, you typically find yourself climbing a steep slope to get to your Tuscan hill town destination. So be ready for a lot of walking if you do this trip, and bring plenty of sunblock and a hat! We were also glad to have brought our trekking poles. Hotels were clean and comfortable, our luggage moved smoothly, and there was good food and wine to be had at every destination.

I had a brilliant experience walking and wine tasting in Tuscany, led by our fantastic guide, Jordan. This trip has a good balance of picturesque walks, wine tasting and city days and offers a great introduction to one of Italy's most beautiful and historic regions. Our itinerary ran seamlessly and there was never a moment where I felt it was too full-on, as we were given plenty of free time between activities. I would do this trip again in a heartbeat!

Stefania - George and I returned last night from our trip of a lifetime! I keep telling people that it felt like a dream. So with laundry and luggage on the floor, I wanted to stop and send you this message! That tells you just how much we enjoyed our trip. Every detail, every transfer, restaurant recommendation, etc. was spot on. We could not have asked for better insight or a better planned trip. The tours.... oh the tours... were fantastic. We learned so much and while we expected the guides to be nice, we were not prepared for just how thorough and nice they would be. Not to mention funny! We enjoyed them as much as we did the sights that they led us through. The hotels were amazing as well. The rooms were great, but their locations were exactly where we needed to be to have the trip we sought after. But I must say that when we stepped onto the property at Hotel Caruso, I felt like we had stepped into a postcard. The flowers and the views were breathtaking. We spent a lot of time just trying to take it all in. There are no words that I can type, and even with a minor dissertation I couldn't cover it all. I have uploaded over 700 pictures and came home 8 pounds heavier! And this morning I went to the Italian grocer/importer to get my fresh mozzarella. I can't even eat food the way I used to. You planned a trip and anniversary celebration that can never be topped. We thank you!!

We thoroughly enjoyed our Via Francigena, Best of Tuscany self guided walk. It was very well sign posted. The app used by UTracks is great. Moving of our bags was seamless.