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Pace of trip: Active
For travellers who love to explore and discover multiple destinations - can include moderate walking and longer days
With our smaller group tours you'll experience a perfect balance between social travel and closer connections; connections to both the incredible places we're exploring and to the kindred spirits you'll meet along the way. A max 20 tour will never have more than 20 travellers on it.
Walk 8km/5miles - 3 hours
The day begins in Badia a Passignano, from where we'll begin our scenic walk towards Castello di Verrazzano. The route gently unfolds through classic Chianti landscapes of vineyards, olive groves and rolling hills. At the castle, we'll enjoy a light lunch with wine tasting, a perfect moment to relax and fully embrace the flavours of the region. In the afternoon, we'll travel by coach to Greve in Chianti, a charming village known for its picturesque main square and authentic local atmosphere.
Meals included: B,L,D
Walk 10 km/6.2 miles - 3 hrs
You can take today to enjoy time for yourself, or join the optional excursion to Florence. We will 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. We will enjoy a light lunch together, followed by some free time.
Meals included: B,D
Walk 8km/5 miles - 3 hours
Today begins with a visit to Volterra, a fascinating hilltop town known for its Etruscan heritage, stone streets and unique atmosphere. During our time here, we'll also observe a traditional alabaster workshop, discovering this ancient local craft.
From here, the walk begins with a scenic downhill route towards Prato d’Era, offering a different perspective of the surrounding landscape.
Later, we'll travel to San Gimignano, where the experience continues with a walk in the surrounding countryside, followed by time to explore the historic centre and its iconic towers.
Meals included: B,D
Walk 5.5km/3.4 miles - 2hrs
Spend today at leisure, or join the optional visit to the medieval village of Certaldo. The day begins with a scenic walk in the Parco Collinare di Canonica, following gentle hillside trails through woodland and cypress-lined paths, offering beautiful views over the surrounding countryside.
After the walk, we'll make our way to the delightful Certaldo Alta, either on foot, or take the opportunity to experience the local funicular. We'll then enjoy a typical Tuscan light lunch, featuring local specialities from the area, including the renowned Certaldo onion.
Meals included: B,D
Walk 6km/3.7miles - 2.5 hours
Today we explore the wide Apennine valley north of Florence, Mugello. The original homeland of the Medici family, it is a patchwork of cultivated fields and rolling lanes, framed by oak and chestnut woods and crossed by quiet waterways, with open views towards Lake Bilancino. Our walk follows a scenic trail through woodland, rural hamlets and protected nature. Towards the end of the walk, we'll enjoy a light farm-to-table lunch at a local restaurant, including the traditional potatoes used for tortelli di patate, before returning to the hotel in the afternoon.
Meals included: B,L,D
Walk 7km/4.3 miles - 2.5 hours
Today we'll enjoy a guided walk through Siena, a city of soaring Gothic architecture and warm terracotta tones, where grand landmarks open onto lively piazzas and quieter lanes lead to hidden courtyards and elegant palazzi. The atmosphere is unmistakably Sienese - timeless, local, and beautifully alive. Later, we'll continue to Monteriggioni, a storybook hilltop village enclosed by its intact medieval walls. Here, time slows along the ramparts and through the tiny streets and it's ideal for a final gentle stroll in a timeless setting.
Meals included: B,D
The Chianti Village Morrocco is situated south of Florence in a quiet and secluded 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
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.
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;
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.
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.
Our full cancellation policy can be found in our booking terms and conditions, section 8.
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.
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From £1,999 per person, prices in pounds sterling (GBP). Flights included, from Heathrow Airport and Manchester Airport. Next available departure 20 April 2027. Prices last updated 22 October 2026 and confirmed at booking.
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