Day 1:

San Gimignano, and Walk Strove to Colle Val d’Elsa

With golden light stretching across the rolling green hills, the Tuscan countrysideis calling. The pace here is slower, coinciding with the wine produced in the region which ismeant to be savoured rather than gulped.

Your first day sees you begin the trek inthe historic village of Abbadia a Isola, following the Via Francigena through therolling Tuscan countryside. Walk past ancient stone farmhouses, cypress-linedpaths, and picturesque landscapes as you make your way toward Colle Val d’Elsa.

Welcome to Tuscany, and to Italy we invite your inner serenity in the countryside. After an informative morning welcome briefing with your guide you will travel to San Gimignano for a visit before today’s trek.

Discover one of the most well preserved Italian medieval sites by marvelling atboth the Gothic and Romanesque architecture of the historical centre, and bysampling some of the regional delights at lunch in town. Your trek begins after lunch, heading to the final destination of Colle Val d’Elsa.

Walk: Abbadia a Isola to Colle Val d’Elsa: 3h – 8km – 300m elevation

Meals included: Dinner

Accommodation: Hotel Palazzo Pacini (or similar)

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Day 2:

Walk Monteriggioni to Siena

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

Walk: La Chiocciola to Monteriggioni: 3h30m – 8km – 150m ElevationMeals

Meals included: Breakfast, Lunch

Accommodation: Hotel Palazzo Pacini (or similar)

Day 3:

Exploring the Chianti Region

Chianti, recognized for its namesake red wine, lies between Florence and Siena in the very centre of Tuscany. Begin the trek from Montefioralle- a small town forming the perimeter around an historic castle. Start the day with a scenic walk through the rolling Chianti countryside, soaking in the breathtaking views of vineyards and olive groves. After working up an appetite, enjoy a delicious, rustic lunch at a traditional farmhouse, where you’ll savour local Tuscan flavours in a relaxed setting.

Walk: Montefioralle to Panzano: 2h30m – 6km – 200m elevation

Meals included: Breakfast, Lunch, Dinner

Accommodation: Borgo Casa al Vento (or similar)

Day 4:

Volpaia to Lamole

Start the day with a scenic transfer to Siena, one of Tuscany’s mostbeautiful medieval cities. Upon arrival, join a local guide for a walking tour through its historic streets, exploring highlights like Piazza delCampo and the stunning Duomo.

After the tour, sit down for a delicious lunch at a local restaurant, enjoying authentic Tuscan flavors. 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.

Take some free time to soak in the atmosphere or browse local shops before heading back to your hotel. Tonight enjoy a special wine pairing dinner.

Meals included: Breakfast, Lunch, Dinner

Accommodation: Borgo Casa al Vento (or similar)

Day 5:

Visit Montepulciano and Walk the Gladiator Trail

UNESCO World Heritage site Val d’Orcia extends from the provinces ofSiena to Grosseto, offering up some of Tuscany’s most picturesque vistas. The Pienza loop trail begins in historic Pienza, a Renaissance citycommissioned by Pope Pius II.

From Pienza, pass the Romanesque parish church of Corsignano as you make your way through the green and gold undulating hillside dotted with cypress trees. After a short time, enter theStrada dei Gladiatori, the exact setting of the panoramic countryside scene from Ridley Scott’s film ‘Gladiator’.

Your morning walk concludes just in time to sample another Tuscan favourite, pecorino cheese. A tasting of locally produced pecorino and ricotta cheeses is served with a glass of Montepulciano wine.

After indulging in a glass of Montepulciano wine, it’s only fitting to visit the town itself. A local guide welcomes you to this ancient hilltop town and provides an in depth walking tour of the old centre.

Walk: The Pienza loop: 2h – 7km – 225m elevation

Meals included: Breakfast

Accommodation: Hotel Vannucci (or similar)

Day 6:

Umbria Cooking with a Local Chef

Taking the time to step away from the hustle of your everyday lifeto intentionally move at a slower pace. Italy is about living andeating well.

Speaking of eating, it’s time to 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, alongside 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.

Meals included: Breakfast | Lunch

Accommodation: Hotel Vannucci (or similar)

Day 7:

Rome

To make the most of your time in Rome, you get to choose between a walking tour or a fully guided Vespa tour.

No matter which way you choose to explore Rome, you will experience the very best the city has to offer. Take a short orientation walk of Rome after arriving to the hotel. If you are up for more walking, join your local Roman guide and walk the historical centre, visiting Piazza Barberini and Piazza di Spagna. Drop a coin into the Trevi Fountain and sip a cappuccino in Piazza Navona.

If you are ready for less walking, more adrenaline, hop on the back of a Vespa with a professional driver and whiz through Rome from Trastevere to the Colosseum and lots more.

Meals included: Breakfast, Dinner

Accommodation: Mama Shelter Roma (or similar)

Day 8:

Rome

Our adventure has come to an end, and you can depart at any time.

Meals included: Breakfast