FROM $7,769

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

Embark on a breathtaking journey through the beautiful regions of Tuscany and Umbria in Italy, as you travel along the winding paths that lead you from the charming city of Florence to the historic city of Rome. Along the way, immerse yourself in the stunning scenery of the vineyards of Tuscany and Umbria, both famous for producing some of the finest wines in the world. This adventure promises to be a once-in-a-lifetime experience, filled with unforgettable moments, delicious food, and an abundance of culture and history to discover.

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

DEPARTURE DATE: September 15, 2024
Countries Visited: Italy


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, wine, and olive oil 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.


  • Visit the historic centre of Pienza
  • A Renaissance city commissioned by Pope Pius II
  • Savour Gelato in Florence on an orientation walk through the city
  • Tour the cellar and vineyard of Molino Di Grace with a farmhouse lunch overlooking the rows of grapes
  • Hike from the tiny village of Strove along the ancient Via Fancigena
  • Sip wine on a vineyard terrace in Tuscany during a lunch-time tasting
  • Walk through medieval towns like Greve Montefioralle and Panzano
  • Sample local cuisines directly from its sources in the many vineyards dotting the hills of Tuscany’s Chianti Region

Travel Dates & Pricing

September 15, 2024from $7,769 CADPer Person
September 15, 2024from $10,518 CADSingle Traveler
September 29, 2024from $7,769 CADPer Person
September 29, 2024from $10,518 CADSingle Traveler

What's Included

  • 9 night small group escorted tour from Florence to Rome
  • 9 breakfasts, 5 lunches, 4 dinners including welcome and farewell dinner
    Complimentary Arrival Transfer
  • Guided walking tour of Florence
  • Lunch at an agriturismo
  • Guided walking tour of San Gimignano
  • Guided walking tour of Montepulciano
  • Guided walking tour of Città della Pieve
  • Cooking class in Umbria
  • Walk Strove to Colle Val d'Elsa
  • Walk Monteriggioni to Siena
  • Walk Montefioralle to Panzano
  • Walk Volpaia to Lamole
  • Walk the Gladiator Trail
  • Pecorino Cheese Tasting
  • Visits to towns in the Italian countryside like Montefioralle, Greve in Chianti, and Montepuliciano
  • Picnic lunches in vineyards
  • Free time in Rome
  • All transport between destinations and to/from included activities
  • CEO (Chief Experience Officer) throughout
  • Taxes


1Sun Sep 15Florence, Italy
2Mon Sep 16Florence, Italy
3Tue Sep 17Tuscany: San Gimignano and Colle Val d’Elsa
4Wed Sep 18Tuscany: Walk Monteriggioni to Siena
5Thu Sep 19Tuscany: Exploring the Chianti Region
6Fri Sep 20Tuscany: Volpaia to Lamole
7Sat Sep 21Tuscany: Visit Montepulciano and Walk the Gladiator Trail
8Sun Sep 22Umbria: Cooking with a Local Chef
9Mon Sep 23Rome: Your OMG Day
10Tue Sep 24Rome

Day 1 – Florence: A Golden Stroll

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.

After an informative welcome briefing with your CEO and a delicious dinner in the heart of Florence, stretch your legs on an evening walk to get some photos of that beautiful golden Florence glow. Speaking of simple pleasures- your evening stroll includes a stop for a gelato at a famous gelateria. Try the pistachio flavour or the fiordilatte. Or both. It’s your first day in Italy, after all. Time to celebrate.

Day 2 – Florence: From the Duomo to the Ponte Vecchio

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.

The only way to truly appreciate Florence is by walking the streets and plazas. After your walking tour, end the morning at a local market where you can enjoy Italian specialties. During the afternoon, choose to join you CEO at the Piazzale Michelangelo for a delicious view of the city and a well earned refreshing drink. There is plenty to do in Florence, so ask your CEO and make sure you make the most of your afternoon.

Day 3 – Tuscany: San Gimignano and Colle Val d’Elsa

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.

Leave Florence and travel southeast, but before you begin to trek, get your body moving by a morning visit to San Gimignano. With the insights of a local guide, 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.

Day 4 – Tuscany: Walk Monteriggioni to Siena

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.

After visiting the village of Monteriggioni, trek along paved and gravel paths passing farms and vineyards. Arrive at your agriturismo in time for an al fresco farmhouse lunch and some well deserved wine. Later continue your journey to the Porta Camollia, the traditional Francigena access to Siena. Explore Siena with your CEO. From Siena take the bus back to your hotel for a free evening.

Day 5 – 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. 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.

Day 6 – Tuscany: Volpaia to Lamole

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.

Day 7 – 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’.

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.

Day 8 – 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!

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 for two nights in Umbria, known as the birthplace of renaissance painter Pietro Vannucci.

Day 9 – 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.

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 back of a Vespa with a professional driver and whiz through Rome from Trastevere to the Colosseum and lots more.

Day 10 – Rome

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

Sounds Like Your Kind of Trip?
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