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Walking in Tuscany

From C$3,099
Duration 8 Days
Departures from: May 2026 - Sep 2026
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From C$3,099
Duration 8 Days
Departures from: May 2026 - Sep 2026

Tour Overview

We're taking you on an 8-day walking adventure through the heart of Tuscany, where every step reveals something extraordinary. Together, we'll wander through the legendary Chianti region, passing sun-drenched vineyards and ancient olive groves before arriving at magnificent Vicchiomaggio Castle for a well-earned wine tasting. We'll explore Florence's cobbled streets on foot, discovering hidden Romanesque treasures and soaking up those iconic panoramic views from Piazzale Michelangelo.

There's plenty of free time built in too, with optional walks through UNESCO-listed Val d'Orcia with its dreamy cypress-lined roads, or explore Leonardo da Vinci's hilltop birthplace. 

We'll delve into the fascinating world of the Medici family, visiting their stunning Renaissance villa and discovering how their passion shaped Florence's golden age.
From medieval Siena's enchanting narrow streets to the rolling Montalbano hills, every moment invites wonder and connection. With fellow travellers by your side and local guides sharing their insider knowledge, you'll experience Tuscany the way it's meant to be discovered: on foot, wide-eyed, and full of possibility.

Your Tour Includes

  • Just You Holiday Director as your host & Specialist Local Guide
  • 7 nights half-board in a 4-star hotel
  • A guaranteed twin or double room of your own
  • 15 included meals: 7 breakfasts, 1 lunch, 7 dinners including a welcome drink
  • Transportation excluding overseas transfers to and from the airport
  • Porterage
  • Complimentary Wi-Fi on board your coach

Included Tour Highlights

  • Medici walk & visit to Poggio a Caiano Villa  
  • Walking tour of Florence 
  • Chianti walk 
  • Vicchiomaggio castle wine-tasting & lunch
  • Small group travel style - Max 20 people on this tour

Tour Itinerary

The Chianti Hills straddling the provinces of Florence, Siena and Arezzo

Day 1 Pistoia

Make your own way to the hotel where your Holiday Director will meet you for your welcome meeting this evening.

Meals included: D

Day 2 Chianti Walk & Vicchiomaggio Castle

6 km/4 mi - 2.5 hrs
Our walk today takes us to the famous region of Chianti. Beginning at the Badia a Passignano Monastery, we'll stroll along quiet country roads, past vineyards and olive groves, and through a landscape dotted with quaint little villages and farmhouses. The walk ends at the magnificent Vicchiomaggio Castle, a well-preserved castle in Tuscany, that's now a winery. We'll see its cellars and then enjoy a tasting of Chianti along with a light lunch on a terrace, overlooking the Tuscan countryside.

Meals included: B,L,D
Florence, Tuscany

Day 3 Florence Walk

10 km/6.2 mi - 3 hrs
We’re going to explore Florence on foot, starting at Piazzale Michelangelo, which sits on a hill and offers stunning views of the city. We’ll then make our way to the city centre, past hidden treasures including one of the finest Romanesque churches in Tuscany and the Porcellino covered market. Enjoy some free time for lunch and perhaps a spot of shopping this afternoon.

Meals included: B,D

Day 4 at Leisure

12 km/7.5 mi - 4 hrs
You can enjoy time to yourself today, or join an optional walk in the Val d'Orcia area of Tuscany. This beautiful area is on the UNESCO World Heritage list, a picturesque region of Southern Tuscany known for it's rolling hills, cypress lined roads and hill top towns.

Meals included: B,D
Vinci

Day 5 at Leisure

9 km/5.6 mi - 2.5 hrs
You’ve a free day to relax at the hotel or explore at your own pace with your travelling companions. Alternatively, join our optional walk from Fornello to Vinci, the birthplace of Leonardo da Vinci. In the company of a Local Guide, we’ll explore this hilltop town and visit the museum dedicated to the artist’s work. Models bring to life the ideas captured in his drawings and provide a fascinating glimpse of his work.

Meals included: B,D
Verrazzano Castle

Day 6 Medici Walk & Poggio a Caiano Villa

8km/5mi - 3hrs
You'll step back in time today and learn about the fascinating history of the Medici family, who rose to political power in Florence during the Renaissance period. Thanks to their success, the family amassed significant wealth and were passionate supporters of the arts. It was due to their influence and generosity that Renaissance culture flourished in the city of Florence.
On our walk today, we'll learn how the Medicis ruled Florence for around three centuries and then we'll head to the magnificent Medici Villa of Poggio a Caiano, before heading to the stunning medieval town of Carmignano, nestled in the Montalbano hills. There will be free time to enjoy lunch here if you wish.

Meals included: B,D
Downtown Siena skyline in Italy

Day 7 at Leisure

Enjoy a day at leisure or join a guided visit to Sienna, the UNESCO-listed medieval city in central Tuscany. This walkable city has a charming, historical atmosphere and some of the most famous landmarks in Tuscany. The Piazza del Campo is one of Europe's best preserved medieval squares, and the Duomo of Siena Cathedral is an Italian Gothic masterpiece. The enchanting streets are narrow and great to explore, although the city is hilly in places.

Meals included: B,D
View of vineyard, Pistoia

Day 8 Departure

Today it's time to say goodbye to your fellow travelers as your trip comes to an end.

Meals included: B
The Chianti Hills straddling the provinces of Florence, Siena and Arezzo

Additional Information

Please note: Most walks take place on paths and tracks. Some will be more strenuous and involve  moderate climbing, plus slopes, tracks, hills, stiles and foot bridges, which may be rough underfoot at times. Sturdy walking shoes and walking poles are essential.

 

What to expect from food and drink in Italian Hotels:
The cuisine that you will enjoy in Italy is based on the Mediterranean diet. It is often very simple with many dishes just featuring a handful of locally sourced ingredients.

Traditionally evening meals are served as a three-course dinner and as a group you will enjoy a set meal together. 

The first course ‘Primi’ will be a local dish of pasta, risotto or occasionally pizza or soup, ‘Secondi’ is the second course which will be a protein-based dish with a local meat or fish served simply with one vegetable or potato on the side. Some food that is served hot in the UK, may be served cold in Italy, for example roast beef and some of those vegetable side dishes.

‘Dolci’ the dessert part of the dinner is a simple traditional dessert of fruit, cake or gelato.

Enjoying a coffee is a typical social activity in Italian culture. An electric kettle is not a common domestic appliance in Italy and therefore it is quite common for hotels to not offer coffee and tea facilities within the rooms, but instead serve in the main restaurant / bar.

Accommodation

Chianti Village Morrocco

The Chianti Village Morocco is situated south of Florence in a quiet location in the Tuscan countryside. The property is surrounded by hills and the nearest town, Tavernelle, is approx 3km away making this hotel a quiet and peaceful stay, while being well located to explore the local area during the days activities. The hotel rooms have either a balcony or patio with a view of the garden or swimming pool. Rooms feature air-conditioning and flat screen TV. The hotel restaurant is open for light lunches and serves dinner daily on the outside patio. The swimming pool is open from May to September

The Chianti Village Morocco is situated south of Florence in a quiet location in the Tuscan countryside. The property is surrounded by hills and the nearest town, Tavernelle, is approx 3km away making this hotel a quiet and peaceful stay, while being well located to explore the local area during the days activities. The hotel rooms have either a balcony or patio with a view of the garden or swimming pool. Rooms feature air-conditioning and flat screen TV. The hotel restaurant is open for light lunches and serves dinner daily on the outside patio. The swimming pool is open from May to September

Optional Excursions

Experience even more of your destination by adding one or more optional excursions to your trip before you set off. Take a look below at the extra trips you can enjoy on this tour

Walk from Fornello to Vinci Museum Entrance

Walk from Fornello to Vinci Museum Entrance

We'll start our walk in Fornello heading towards Vinci, the birthplace of Leonardo da Vinci. In the company of a Local Guide, we'll explore this hilltop town and visit the museum dedicated to the artist's work. Models bring to life the ideas captured in his drawings and provide a fascinating glimpse of his work.
We'll start our walk in Fornello heading towards Vinci, the birthplace of Leonardo da Vinci. In the company of a Local Guide, we'll explore this hilltop town and visit the museum d...

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Walk in Val d'Orcia

Walk in Val d'Orcia

The Val d'Orcia area of Tuscany is on the UNESCO World Heritage list, a picturesque region of Southern Tuscany known for it's rolling hills and medieval hilltop towns. Todays guided walk will begin in the town of Pienza, known as the ideal Renaissance city, it was built in the 15th Century to an urban plan and has charming streets and incredible views over the surrounding area. We will take a circular route of 7km through this stunning area, walking through landscapes reminiscent of the film Gladiator, through gentle hills and roads lined with cypress trees. At the end of the walk we will enjoy lunch in a local restaurant in Pienza.
Available May - Sep
The Val d'Orcia area of Tuscany is on the UNESCO World Heritage list, a picturesque region of Southern Tuscany known for it's rolling hills and medieval hilltop towns. Todays guide...

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Guided visit to Siena

Guided visit to Siena

Siena is one of the most perfectly preserved medieval cities in Europe which you can visit on this optional excursion. The old medieval centre has been declared an UNESCO world heritage site due it’s enchanting narrow streets, lined with palaces and mansions, which lead to the spectacular Piazza del Campo.
Available May - Sep
Siena is one of the most perfectly preserved medieval cities in Europe which you can visit on this optional excursion. The old medieval centre has been declared an UNESCO world her...

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