Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria image
Save 25% off, auto-applied, ends 2026-06-19
Operated by G Adventures

Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria

From
CAD 5,654
Duration
10 days
Countries
Italy
Activity
moderate

The adventure

It’s never been hard to fall under the spell of Italy’s romantic atmosphere. On this 10-day adventure there’s no doubt you’ll fall deeper in love as you wine and dine through the Tuscan countryside, encounter medieval towns, sprawling vineyards, and the historic city centres and grand piazzas of some of the most charming towns in the country. Hike along scenic pilgrim routes through quaint villages like Greve, Montefioralle, and Panzano, and stop for visits to wine cellars paired with cheese, and wine tastings along the way. Finally, a perfect blend of invigorating scenic walks and complete immersion into the historic food culture of Italy, combining for the ultimate rejuvenating and inspiring experience.

At a glance

Duration
10 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: Florence to Rome, Walking the Vineyards of Tuscany and Umbria image

Day by day

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

Italy

Day 1As the sun sets in Florence
Beautiful nighttime scenery of Florence's Arno River with illuminated buildings and bridge reflections.Florence
As the sun sets in Florence, the city centre becomes bathed in a golden hue as the lights come on, welcoming locals and travellers alike to head out into the city, to dine together and celebrate life's simplest pleasures. The birthplace of the renaissance, Florence remains a fashion and culture icon in the modern world. With so much art, history, and architecture to take in, there is no time to waste. Welcome to Florence, and to Italy, and we invite you to explore the old and the new, the grand and the simple, all in one of the world's most beautiful countries.
Map showing Florence
Day 2Standing before the Cattedrale di Santa Maria del FioreFlorence
Monochrome image of the historic Ponte Vecchio bridge over the Arno River in Florence, Italy.Florence
Standing before the Cattedrale di Santa Maria del Fiore, the Duomo, is one of those moments in life where you feel truly small. To take in the magnitude of what the cathedral represents is to transport yourself back in time to the 13th century. Could the people who began to build this magnificent structure have ever imagined that 800 years later people would still come to marvel at its beauty. This morning join your expert guide for a walking tour and see the Duomo, Signoria Square and then head over to the Ponte Vecchio, you will only just be scratching the surface of what there is to see.
Map showing Florence
Day 3The Tuscan countryside is callingFlorence
A captivating aerial view of Florence showcasing its historic architecture and iconic landmarks.Florence
The Tuscan countryside is calling. Over the course of the next 5 days, move through Tuscany and Umbria by walking from village to village. The pace here is intentional-many stops are made along the way to ensure you see and experience the true essence of these beautiful places. Your first day sees you begin the trek in the village of Strove walking the Via Fancigena until you reach the Elsa River. Cross the river on foot, wading ankle deep in the blue water.
Map showing Florence
Day 4Monteriggioni 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 5ChiantiFlorence
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 6Start 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 7UNESCO 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 8Walking 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 9AdmittedlyRome
The Colosseum stands majestically amidst bustling Rome, an iconic remnant of ancient architecture.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.
Map showing Rome
Day 10Your 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 EIFR260620 · ends 2026-06-19 · auto-applied
DatesPrice / personAvailability
20 Jun 202629 Jun 2026CAD 5,654On requestBook my trip
21 Jun 202630 Jun 2026CAD 7,539unknownBook my trip
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