EXCLUSIVELY FOR SOLO TRAVELLERS

Over 25 Years Expertise

Your Money is 100% Protected

Holiday Assurance Guarantee

No Single Supplement

Walking in Tuscany

From £1,709
Duration 8 Days
Departures from: May 2026 - Sep 2026
Book Now
From £1,709
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
  • Return flights from London
  • 7 nights in a 3-star hotel
  • A guaranteed twin or double room of your own
  • 11 included meals: 7 breakfasts, 1 lunch, 3 dinners including a welcome drink
  • Overseas transfers, other transportation & 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 UK - Pisa

Today, you will fly to Pisa and on arrival we will transfer you to your hotel. This evening, you will meet your fellow travellers over a drink and dinner.

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 Pisa - UK

Today transfer to the airport for your return flight to the UK.

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.

  1. Memorable Moment

    Visit the bustling Porcellino market where stall holders trade just 
    as their ancestors did before them. Follow tradition and rub the boar 
    statue's snout for prosperity.

Accommodation (as specified or similar)

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 holiday 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...

Read less

Read more

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...

Read less

Read more

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...

Read less

Read more

Further Information

Deposit information

When you book a holiday, you will be asked to pay a deposit, this will be made clear at the time of booking. In most cases we will charge the following deposit amount;

  • UK Holidays - £150 per person
  • European Holidays - £200 per person
  • Worldwide Holidays - £400 per person
  • Ocean and River Cruise - £400 per person


On some holidays we may charge a slightly higher deposit, to cover any costs we have to pay immediately to secure your booking with our suppliers. This will be made clear at the time of booking.

If you choose a tour that is within 84 days of departure you will need to pay the full balance when you book.

Our cancellation policy

If you decide to cancel your confirmed booking you must notify us (or your travel agent) in writing, as soon as possible. Since we incur costs in cancelling your arrangements, you will have to pay the applicable cancellation charges up to the maximum shown below.

  • More than 75 days before departure - Loss of deposit only
  • 43 - 74 days - 50% of tour price
  • 29 - 42 days - 75% of tour price
  • 15 - 28 days - 90% of tour price
  • Day of Departure - 14 days - 100% of tour price

Our full cancellation policy can be found in our booking terms and conditions, section 8.

How do I find out Entry and Health Requirements for my holiday?

We have partnered with Sherpa, an on-line self service tool that allows you to search up-to-date information regarding travel entry requirements for all countries and also allows you to apply for eVisas or eTAs via their on-line portal. Just click on this link to find out more – Travel requirement & Visa Service.

You can also refer to the Foreign Travel Advice section on the gov.uk website: Foreign travel advice - GOV.UK (www.gov.uk). Click on your destination and then click on 'Entry Requirements'. For Health Requirements, the Department of Health also offers travellers health advice on www.travelhealthpro.org.uk, click on country information to locate your destination.

It is important to remember that passport, visa and health requirements can change before departure; therefore, we recommend you regularly familiarise yourself with the latest requirements before you travel. If you cannot travel because you have not complied with any passport/entry/immigration requirements, we are unable to accept any responsibility.

For some destinations, it is not always discernable that a visa is required for entry at the border.  For example, for some customers, to travel to the United States, an ESTA may be required. For Canada, an ETA and to India, an e-visa may be needed. Please do check your requirements to avoid any unnecessary cost and delays.

 

Solo tour holidays you may also like

  1. Amalfi Coast
    Bestseller

    Walking the Amalfi Coast

    Admire remote picturesque villages and stunning views as you get out and about in the great outdoors and explore the beautiful Amalfi Coast on foot.

    • Return flights
    • 7 nights in a 3-star hotel
    • 15 included meals: 7 breakfasts, 1 lunch, 7 dinners

    8 days from
    £1,799
    was £1,949
    Explore
  2. Walking in Crete

    Walking in Crete

    Enveloped in the myths and legends of Greek gods, explore Crete, an island paradise, on our tour led by expert Local Guides.

    • Return flights
    • 7 nights in a 4-star hotel
    • 16 meals included - 7 breakfasts, 2 lunches, 7 dinners

    8 days from
    £2,329
    was £2,579
    Explore