We will meet at our hotel in the historic center of Florence.

We will climb to the Panoramic Terrace of the Piazza de Michelangelo for sweeping views of the iconic sunset over the Arno River. Later, we will explore the bridges of Tuscany which are magical at night.

We will meet our Certified Tour guide and local historian, Elizabeta, for a private tour of Florence. We will see the most important landmarks of the Renaissance and hear the fascinating stories of the Medici Family. You’ll have time for a leisurely lunch in one of the beautiful piazzas and shopping before we leave for the hill-top town of San Miniato, the trailhead for our walk. Later that evening, we will have a celebratory dinner at a Michelin-rated restaurant overlooking the Tuscan hills.

We will walk 14 miles through beautiful rolling hills to Gambassi TERME. This is our most challenging day. But our efforts will be richly rewarded at our villa that overlooks 150 acres of vineyards, olive groves, and a refreshing pool.

We will walk 9 miles through the hill-top town Gambassi Terme and across vineyards for stunning views of the skyline of San Gimignano, also known as Manhattan of the Middle Ages. It once had 72 towers! But now has 13 remaining towers. San Gimignano is a UNESCO World Heritage Site. Within the churches and palazzos, there are many noteworthy 14th and 15th-century frescoes. Today it is famous for saffron, pecorino cheese, and Vernaccia de San Gimignano white wine.

Our 4-star hotel is located within the city walls in a 14th-century building. San Gimignano is a busy tourist destination during the day, but after the day-trippers leave,  it’s purely magical.  Grab a glass of wine and watch the sunset over the Tuscan Hills.

We will walk approximately 8 miles from San Gimignano to Colle Val d’Elsa.

Today we have a short but beautiful walk from Colle Val d’Elsa to Strove. We will walk through the shaded Elsa River park which has a series of small waterfalls with a constant, pleasant breeze. This river gets its bright blue color from the limestone in the river bed. Our destination is a 17th-century village (Borgo) that has been converted to a 4-star resort villa that sits on 20 acres of parkland with a pool.

On day 7, you can sleep in, have a leisurely breakfast, and enjoy the pool and park-like setting before making the 4-mile walk to the hilltop village of Monterriogioni.

Walk approximately 12 miles from Monteriggioni to Siena.

After check-in, you’re free to explore the shops, museums, and churches of Siena. We will have a sunset dinner on the terrace of our 4-star hotel overlooking the hills.

Free morning in Siena. In the evening we will take a car to a 16th-century villa that overlooks the Tuscan hills for wine tasting and a cooking class.

We will share a final, farewell breakfast to celebrate our wonderful adventure together.

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You are free to explore the shops, museums and Renaissance churches of Siena. The historic city center of Siena is a UNESCO world heritage site.