Italy: Tuscany and Umbria Vineyard Walks - G Adventures Tour
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G Adventures Guided Tour

Italy: Tuscany and Umbria Vineyard Walks

8 Days 4 Departures
From $3,679 per person

Tour Overview

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, and connect with the local beauty. 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.

Tour Summary

Duration8 Days / 7 Nights
OperatorG Adventures
Departures4 in 2026
Starting From$3,679 pp

Tour Route

Map of your 8-day journey

Italy: Tuscany and Umbria Vineyard Walks route map

Day-by-Day Itinerary

8 days through your journey

Day 1

Tuscany: San Gimignano, and Walk Strove to Colle Val d'Elsa

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. Your first day sees you begin the trek in the historic village of Abbadia a Isola, following the Via Francigena through the rolling Tuscan countryside. Walk past ancient stone farmhouses, cypress-lined paths, and picturesque landscapes as you make your way toward Colle Val d'Elsa. Welcome to Tuscany, and to Italy we invite you inner serenity in the countryside.
Day 2

Tuscany: 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.
Day 3

Tuscany: 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.
Day 4

Tuscany: Volpaia to Lamole

Start the day with a scenic transfer to Siena, one of Tuscany’s most beautiful medieval cities. Upon arrival, join a local guide for a walking tour through its historic streets, exploring highlights like Piazza del Campo and the stunning Duomo. After the tour, sit down for a delicious lunch at a local restaurant, enjoying authentic Tuscan flavors. 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.
Day 5

Tuscany: Visit Montepulciano and Walk the Gladiator Trail

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

Umbria: Cooking with a Local Chef

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

Rome: Your OMG Day

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.

Departure Dates & Pricing

4 departures available

Departure DateEnd DateStatusPrice Per Person
Sep 7, 2026 Sep 14, 2026 Available $3,679per person Get Quote
Sep 29, 2026 Oct 6, 2026 Available $3,679per person Get Quote
Oct 5, 2026 Oct 12, 2026 Available $4,399per person Get Quote
Oct 20, 2026 Oct 27, 2026 Available $3,999per person Get Quote

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