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Italy: Tuscany and Umbria Vineyard Walks

8 days/7 nights

Guided Small Group Adventure Tour
Guide Price €3,669 per person (based on 2 adults sharing)

Spend time in the Tuscan countryside in landscapes dotted with farmhouses and castles all while experiencing Italy in perfect harmony with the land. Hike the same paths spiritual pilgrims once walked long ago, sit down for a picnic lunch in the vineyards of Lamole di Lamole and learn about the food and drink you consume in a storybook setting. Italy has long been known for its atmospheric cuisine, on this trip you’ll get a taste of Tuscany and its own unique identity and thousand-year-old history.  

Highlights:
  • Hike from the tiny village of Strove along the ancient Via Fancigena
  • Sip wine on a vineyard terrace in Tuscany during a lunch-time wine tasting
  • Walk through medieval towns like Greve in Chianti
  • Visit Montefioralle and Panzano
  • Sample local cuisines directly from the source within the many vineyards dotting the hills of Tuscany’s Chianti Region
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Itinerary

Day 1  Florence to Tuscany    
Arrive into Florence and travel to stunning Tuscany. 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.  

Day 2  Tuscany    
Monteriggioni is your quintessential Tuscan medieval walled village. Follow part of the ancient Francigena way into Siena. Step back in time as you walk past donkeys in green pastures and lush vineyards as the Tuscan countryside unfolds before you. Walk up to the main door of the Hermitage of San Leonardo al Lago and knock-your local host will be waiting. Enter and admire the frescoes painted throughout the church.

Day 3  Tuscany      
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.

Day 4  Tuscany  
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.  

Day 5  Tuscany  
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'.  

Day 6  Tuscany to Umbria      
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!  

Day 7  Umbria to Rome  
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.  

Day 8  Rome      
Your adventure has come to an end, and you can depart at any time.

Departs: Selected departures, May - Oct  

Price & Inclusions

Guide Price €3,669 per person (based on 2 adults sharing)

Inclusions
  • 7 nights hotel accommodation
  • 7 breakfasts, 5 lunches & 3 dinners
Not Included
  • International flights
New offers every day!

We negotiate new offers daily from discounted flights, tours and vehicle hire to free upgrades, added value and unique inclusions. Please call for our latest offers.

The tour itinerary, inclusions and departures are based on travel from 01/01/2024 to 31/12/2024. Guide prices are based on twn/dbl share, are subject to availability and may vary by departure date. For travel outside of these dates, the itinerary and inclusions may vary to that shown above - please ask for details.
Offers are subject to availability and restrictions may apply.

Flights

As we can offer you such a flexible choice of flights, we don't include international airfares with our tour prices. The price you pay will be determined by the time of year you travel, your departure airport, airline and availability.

Your Trailfinders Travel Consultant will be able to find the best flights to suit you and your choice of tour. Contact us for our latest flight offers or take a look at our flights pages for a general idea of prices.

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