Italy: Tuscany and Umbria Vineyard Walks image
Save 25% off, auto-applied, ends 2026-06-19
Operated by G Adventures

Italy: Tuscany and Umbria Vineyard Walks

From
CAD 4,537
Duration
8 days
Countries
Italy
Activity
moderate

The adventure

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.

At a glance

Duration
8 days
Route
Florence → Rome
Countries
Italy
Activity level
moderate
Style
Active & Multi-Sport, Culture & History, Food & Drink, Trekking & Hiking
Group size
Ask
Flights
Not included
Solo travellers
Welcome

Where you'll go

Italy: Tuscany and Umbria Vineyard Walks image

Day by day

View of a historic hilltop town surrounded by lush greenery under cloudy skies.
Your journey through

Italy

Day 1With golden light stretching across the rolling green hills
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 2Monteriggioni is your quintessential Tuscan medieval walled villageAfter the hike, explore Monteriggioni’s charming streets and well-preserved medieval walls. Then, relax and enjoy a well-earned lunch with local flavors before heading back to Colle di Val d’Elsa, where you will have some free time to explore this historic town at your own pace.
After the hike, explore Monteriggioni’s charming streets and well-preserved medieval walls. Then, relax and enjoy a well-earned lunch with local flavors before heading back to Colle di Val d’Elsa, where you will have some free time to explore this historic town at your own pace.
Day 3ChiantiFlorence
Beautiful nighttime scenery of Florence's Arno River with illuminated buildings and bridge reflections.Florence
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.
Map showing Florence
Day 4Start the day with a scenic transfer to Siena
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 5UNESCO World Heritage site Val d'Orcia extends…
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 6Walking the Italian countryside is the ultimate gift…
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 7AdmittedlyRomeTake 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.
The Colosseum stands majestically amidst bustling Rome, an iconic remnant of ancient architecture.Rome
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.
Map showing Rome
Day 8Your adventure has come to an end, and you can depart at any time
Your adventure has come to an end, and you can depart at any time.

Discover Italy

A glimpse of the destination you'll explore.

Picturesque landscape of Lake Garda with a distant island under a summer sky.
Overcast day in Tuscan hills featuring cypress trees and traditional stone house.
A picturesque town nestled by cliffs on the Amalfi Coast, Italy.
Picturesque view of Tuscany's rolling hills, vineyards, and Italian villas under a clear summer sky.
Beautiful view of Ponte Sant'Angelo spanning the Tiber River in Rome, Italy under a clear sky.

Upcoming departures

Last Minute 25% off EIFG260622 · ends 2026-06-19 · auto-applied
DatesPrice / personAvailability
22 Jun 202629 Jun 2026CAD 4,537On requestBook my trip
23 Jun 202630 Jun 2026CAD 6,049unknownBook my trip
Operated by G Adventures

A TripFinder-trusted operator. We compare the trip and handle your booking with a real advisor — you travel under the operator's terms.

Book my trip →

More Europe adventures

Zagreb to Santorini: 35 Unforgettable Days image
G Adventures
Save 20%

Zagreb to Santorini: 35 Unforgettable Days

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 35 days · Easy

fromCAD 7,679
Next: 21 Jun
Zagreb to Athens: Monasteries & The Mediterranean image
G Adventures
Save 20%

Zagreb to Athens: Monasteries & The Mediterranean

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 29 days · Easy

fromCAD 5,839
Next: 21 Jun
Intrepid Travel Montenegro Kotor
Intrepid Travel
Deal

Vienna to Dubrovnik

Austria, Bosnia and Herzegovina, Croatia, Czechia, Hungary, Montenegro, Poland, Serbia, Slovakia · 29 days · Easy4.9(9)

fromCAD 6,923
Next: 20 Jun