Italy: Tuscany and Umbria Vineyard Walks

With golden light stretching across the rolling green hills, the Tuscan countryside is calling. The pace here is slower, coinciding with the wine produced in the region which is meant to be savoured rather than gulped. Throughout this picturesque adventure, move through Tuscany and Umbria by walking from village to village. Your first day sees you begin the trek in the village of Strove walking the Via Fancigena until you cross the Elsa River on foot, wading ankle deep in the blue water. Welcome to Tuscany, and to Italy, we invite you to find you inner serenity in the countryside.

After an informative morning welcome briefing with your CEO 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 at both the Gothic and Romanesque architecture of the historical centre, and by sampling some of the regional delights at lunch in town. Your trek begins after lunch, heading to the final destination of Colle Val d'Elsa.

Additional Information: We recommend that you book a pre-night at our hotel or nearby for the night prior so that you don't miss the group transfer.

ACTIVITY: MORNING Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Today enjoy the walled town of San Gimignano on a guided visit. Feel yourself be lured by the palpable sense of history and medieval streetscapes in this enchanting rural setting.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Begin in the tiny village of Strove and walk along the ancient Via Fancigena to the Elsa River. Walk through the park, over bridges, and bask in the ice-blue colour of the water.

Length: 8km (5 miles)
Duration: 3 hours
Elevation: approximately 100m

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.

After hiking toward 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.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Begin at the Chiocciola and Villa Castles and make your way through the dense bush, heading toward the enchanting Monteriggioni. Walk on dirt paths, gravel roads, and narrow trails.
Elevation: 150m

ACTIVITY: Set out on a short walking tour of Siena with your CEO to gain a sense of Italy's loveliest medieval city.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

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. Trek from the wavy hills of the Chianti region, along the dusty dirt road that winds through rows of vineyards and the silvery foliage of olive groves, before reaching the provincial road that leads to the hamlet of Panzano. Your reward for another beautiful walk? Lunch at a local winery with a pairing of local wines of course.

After a decadent and leisurely lunch, continue on to Greve in Chianti, considered the "gateway" to the Chianti region. Greve in Chianti is formed around a beautiful triangular piazza, at the centre of which is a statue of the explorer Giovanni da Verrazzano, one of the town’s most illustrious sons, who went down in history for discovering the bay of New York. End the day relaxing with a cold drink at your Tuscan Villa perched above the vineyards.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Montefioralle is one of the gems of the Chianti region and sits atop a high plain. The houses in the small town surround the historic castle. In some places the town is still protected by the original defense walls. Spend some time walking around and stretching those legs after breakfast.

ACTIVITY: Start in the rolling hills of the Chianti region and continue along a dusty, dirt road winding through vineyard rows and enjoy this storybook setting all the way to the hamlet of Panzano.

Distance: 6km
Duration: 2.5 hours
Elevation: 150-200m

ACTIVITY: Enjoy a guided tour of the Molino di Grace vineyard and cellar with an included private farmhouse lunch.

ACTIVITY: Known as the gate to the Chianti region, Greve in Chianti is a town dating back to the Middle Ages.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

From medieval village to medieval village, through the vineyards of Chianti, your walking today 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.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Leave Volpaia and climb upwards towards Monte Querciabella, the highest point of the hike, before continuing slightly downhill to reach Lamole.


Elevation gain: 250m
Distance: 8-9km
Duration: 3 hours

ACTIVITY: Sit down for a delicious picnic lunch surrounded by the natural and the gorgeous landscape of Lamole. Discover the traditions surrounding the wines linked to this territory on a guided visit to a local vineyard's wine cellars.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Relax and enjoy an apertivo along with views of the Italian countryside on a panoramic terrace before a wine and dinner experience. Sit down together and pair 4 wines with 4 local dishes and sip an apertivo and fully immerse yourself in the Chianti region.

UNESCO World Heritage site Val d'Orcia extends from the provinces of Siena to Grosseto, offering up some of Tuscany's most picturesque vistas. The Pienza loop trail begins in historic Pienza, a Renaissance city commissioned 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 the Strada 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. Here we leave Tuscany and head into Umbria to Città della Pieve.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Begin in the historic center of Pienza before hiking to the Romanesque parish church of Corsignano and ending up at an old film location for "The Gladiator" before returning to Pienza.

Elevation gain: 225m
Distance: 6km
Duration: 2 hours

ACTIVITY: Taste a variety of pecorino cheeses in Pienza. The cheeses will be accompied by fruit compotes and samples of ricotta cheese. Wine and water will be provided. Learn about each of the cheeses and the production process as you sample.

ACTIVITY: Enjoy a visit to Montepuliciano with a local guide. Nestled between the Val D'Orcia and Val di Chiana this quintessential Tuscan medieval village is a must-see. Think glowing green landscape, hills unraveling for miles, and castle ramparts to explore.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

Walking the Italian countryside is the ultimate gift to yourself. Taking the time to step away from the hustle of your everyday life to intentionally move at a slower pace. Italy is about living and eating 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.

ACTIVITY: See Città della Pieve on a walking tour led by a local guide. The city is considered a historic medieval centre and was built of bricks in different shades of dark pink. A distinguishing marker from other Umbrian towns which are mainly made of stone. The best feature of this town are its many winding, maze-like alleys which acted as a defensive system, making the town impenetrable to enemies. The narrow streets also helped shield the town from the heat of the summer sun and the winter winds.

ACTIVITY: Take part in a cooking class surrounding by breathtaking views of the Italian countryside. Learn from a professional chef and cook handmade pasta using traditional Umbrian recipes and pair your creations with local wines.

Admittedly, Rome is one of those cities that is pretty OMG worthy on its own. If you have an entire week, its a great city to get lost in, wandering from neighbourhood to neighbourhood. 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.

TRANSPORT: Settle in and scan the scenery from the convenience of a private vehicle.

ACTIVITY: Enjoy a brief walk with your CEO. They will give you some tips on finding things like supermarkets, main squares, and ATMs. For more specific or in-depth information, an official guided tour is recommended.

ACTIVITY: Option 1: There are many ways to see Rome, but sometimes the best way is on foot. Discover the Eternal City on walks through the squares that have marked history. Start from Piazza Barberini, become enchanted by the charm of the Spanish Steps, and get ready to turn your luck with a coin toss into the Trevi Fountain. This leisurely walk continues towards the Pantheon and Sant'Ivo della Sapienza, ending in Piazza Navona.

Option 2: When in Rome... live "la dolce vita". To see the Eternal City like the locals, hop onto a Vespa! Cruise around the city and visit Rome's must-see landmarks with a local guide. Your professional driver will show you the majesty of ancient monuments such as the Colosseum, Keyhole, Trastevere District, or even the view of the Roman Forum from the top of the Capitol hill.

FREE TIME: Take advantage of free time in Rome and opt for a CEO-led orientation walk of the city or simply keep exploring on your own before your final group dinner tonight.

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

ACTIVITY: Not ready to leave? Your CEO can help with any onward travel arrangements you require.