Hiking Tours in Siena

Private Tour Siena San Gimignano and Chianti from Cortona

Spectacular.

This trip was incredible. Luca was a stellar driver, knows everything about the area. The winery is fantastic and worth every penny and more. This was a day we will never forget. If you do nothing else, do this!

Tuscany Hiking Tour from Siena Including Wine Tasting

Historical, Picturesque, Interesting but hot in July. Rewarded with wine tasting

Our guide Keko was very friendly and knowledgeable about the countryside, plants and history of his area of Birth. We were a small group of 6 and Keko went at our Pace, which we was grateful for in the July heat. The 7km trek, which was part of the pilgrimage route we walked to Monteriggioni was picturesque and interesting. The tour finished with wine tasting in Monteriggioni.

Hiking Tuscany & Chianti Wine - 3 Organic Wineries with lunch

A perfect day in Chianti

Stefano began by patiently answering our questions weeks before the trip. He checked in with us as our date approached and then arrived to pick us up in Florence city center at the pre-planned time and location with his clean, spacious van. Our trek included our two adult children. Stefano was the perfect host. His English is impeccable, and he was kind to share some history of Florence, the Tuscany region, and more as we arrived in Chianti. When we realized we accidentally brought sparkling water, he stopped to be sure we had the chance to get still water. Our family of four includes a landscape architect, an ecologist, and a college minor in sustainable agriculture. He was patient to answer so many questions about the area, plants, and flowers that we saw. Our hike was exactly as expected in terms of duration and difficulty, but it was far more beautiful and peaceful than anything we could have imagined. Each winery was unique, but all welcomed us, gave us detailed information about their grapes, olives, and history, and each shared their delicious products. We had the opportunity to purchase wine and olive oil from all, but none were high-pressure situations. Our first case arrived within days of our return home! Stefano was careful to be sure we were each comfortable and he gave accurate details along the way so that we would understand how far to the next stop. While we visited the final winery, he somehow retrieved the van and had it cooled and ready to take us back to Florence. Our only regret is not staying in the area longer and having him take us to Cinque Terre too! We highly recommend Stefano, Out of the Box Florence, and look forward to returning in the future for one of his other treks! Grazie Mille!