On arrival, you will be met and transferred to your accommodation for the following 2 nights. Rest of day at leisure, until your welcome dinner this evening. 
Stay: Hotel Club Florence, or similar   (D)

This morning join your expert guide for a walking tour and see the Duomo, Signoria Square and then head over to the Ponte Vecchio; you will only just be scratching the surface of what there is to see. The only way to truly appreciate Florence is by walking the streets and plazas. After your walking tour, end the morning at a local market where you can enjoy Italian specialties.

Afternoon at leisure.

Stay: Hotel Club Florence, or similar   (B)

Over the course of the next 5 days, walk from village to village through Tuscany and Umbria. The pace here is intentional-many stops are made along the way to ensure you see and experience the true essence of these beautiful places. Your first day sees you begin the trek in the village of Strove walking the Via Fancigena until you reach the Elsa River. Cross the river on foot, wading ankle deep in the blue water.

Before you begin trekking, visit San Gimignano. With the insights of your local guide, discover one of the most well preserved Italian medieval sites by marveling at both the Gothic and Romanesque architecture of the historical center, and by sampling some of the regional delights at lunch in town. After lunch, walk 5 miles to Colle Val d'Elsa.

Stay: Hotel Palazzo Pacini, or similar  (B, L)

Monteriggioni is a quintessential Tuscan medieval walled village. Follow part of the ancient Francigena way; step back in time as you walk 5 miles past donkeys in green pastures and lush bushes as the Tuscan countryside unfolds before you.

In the village of Monteriggioni, enjoy lunch at La dama nella Vigna with some well-deserved wine. Once satisfied, visit Monteriggioni before continuing your journey to Siena where you’ll explore with your guide. From Siena, take the bus back to your hotel for a free evening.

Stay: Hotel Palazzo Pacini, or similar  (B, L)

Chianti, recognized for its namesake red wine, lies between Florence and Siena in the very center of Tuscany. Begin the 4-mile walk from Montefioralle. Trek from the wavy hills of the Chianti region along the dirt road that winds through rows of vineyards and olive groves, before reaching the hamlet of Panzano. Your reward for another beautiful walk is lunch at a local winery with a pairing of local wines of course. 

After lunch, continue on to Greve in Chianti. End the day relaxing with a cold drink and dinner at your Tuscan Villa perched above the vineyards.

Stay: Borgo Casa al Vento , or similar (B, L, D)

From medieval village to medieval village, through the vineyards of Chianti, todays 5-mile loop walk sees you leaving Volpaia walking up towards Monte Querciabella, the highest point of the day. Carry on to Poggio del Quercetino and then downhill to Lamole, famous for its terraced vineyards, where you take a luscious rest in the form of a picnic lunch among the vines.

After lunch, sample four varieties from the local Tuscan estates, continuing to learn not only about the process of wine making in Tuscany, but about the people who make their life here in Chianti. Tonight enjoy a special wine pairing dinner.

Stay: Borgo Casa al Vento, or similar (B, L, D)

UNESCO site Val d'Orcia extends from Siena to Grosseto, offering some of Tuscany's most picturesque vistas. The 4-mile Pienza loop trail passes the Romanesque parish church of Corsignano and continues through green and gold undulating hillside dotted with cypress trees. After a short time, you will enter the Strada dei Gladiatori, the exact setting of the panoramic countryside scene from Ridley Scott's film 'Gladiator'.

After your walk, sample another Tuscan favorite, pecorino cheese. A tasting of locally produced pecorino and ricotta cheeses is served with a glass of Montepulciano wine.  A local guide welcomes you to this ancient hilltop town and provides an in depth walking tour of the old center. Here you leave Tuscany and head into Umbria to Città della Pieve.

Stay: Hotel Vannucci, or similar (B, S)

Walking the Italian countryside and taking the time to step away from the hustle of your everyday life to intentionally move at a slower pace is the ultimate gift to yourself. Spend the morning with a local chef learning to prepare some of Italy's most loved dishes. A tagliatelle with ragù perhaps, or a creamy tiramisú. Buon Appetito!

After you devour the fruits of your cooking labor, and a few glasses of delicious wine, the afternoon is yours to spend at leisure. A local guide will lead a walking tour of Città della Pieve, our home while in Umbria, known as the birthplace of renaissance painter Pietro Vannucci.

Stay: Hotel Vannucci, or similar (B, L)

Travel by vehicle to Rome, where you can explore the city independently, or opt to add a guided walking tour. Or, if you are ready for less walking and more excitement, on the back of a vespa driven by a professional driver/guide. 

Enjoy a farewell dinner this evening.

Stay: Mama Shelter Roma, or similar (B, D)

Your journey is over after breakfast this morning...unless you opt to add extra time in Rome.

(B)