Tuscany Walks & Chianti Wines

Explore winding wineyards

Discover picturesque towns and delicious wines

A wonderful trip from beginning to end!

” I had a brilliant experience walking and wine tasting in Tuscany, led by our fantastic guide, Jordan. This trip has a good balance of picturesque walks, wine tasting and city days and offers a great introduction to one of Italy’s most beautiful and historic regions. Our itinerary ran seamlessly and there was never a moment where I felt it was too full-on, as we were given plenty of free time between activities. I would do this trip again in a heartbeat!

Most Inspirational Moment

Visiting Florence – a city steeped in history and culture!

Thoughts on Group Leader

Fantastic – Jordan went above and beyond to ensure we enjoyed our holiday.

Advice for Potential Travellers

Plan ahead for the free day. There are activities you can book through the hotel but availability can be limited.

Activity level exodus
Tusany map

All the things you need to know

Start at Hotel Le Renaie, the welcoming family-run hotel 4mi (6.5km) from San Gimignano. In the evening, your guide will hold a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.

If you have extra days at hand and are willing to extend your adventure, consider booking additional nights in Pisa or Florence. 

Meals included: Dinner

Get ready for a day full of history and nature as you explore one of the most popular sections of the Via Francigena, which links the villages of Gambassi Terme to San Gimignano. The Via Francigena is an ancient pilgrimage route that links Canterbury in the UK to Rome; the full trip takes well over 90 days, but this section is far gentler, cutting through olive groves and vineyards. Later in the afternoon, you head to an eco-friendly wine estate near Certaldo where your discovery of Tuscan wines will be taken to the next level with a sensory and aroma experience, accompanied by mouth-watering traditional appetisers.

Dinner this evening is back at the hotel, where you have time to relax a little more, perhaps with a game of billiards or another glass of local wine on the garden-view terrace.

Distance covered: 6mi (9km)

Meals included: Breakfast, Dinner

This morning, you will enjoy a local history in the heart of the Chianti area, covering the scenic route in a circular walk. Cut through woodlands, where you can admire the emerald vineyard valleys. In the afternoon, you have some free time to wander around and maybe join an optional tasting  of the much-acclaimed chianti classico at one of the many local wineries.

Distance covered: 5mi (8km)

Meals included: Breakfast

After breakfast, head to the centre of Siena for a day exploring this fascinating city. Have time to visit the numerous museums and stunning duomo (cathedral) and to relax in one of the many outdoor cafes in Piazza del Campo, home of the Palio horse race. Please note, shoulders should be covered when entering the cathedral. You may also like to visit the many boutiques specialising in local products and Italian fashion. In the afternoon, you will learn about Tuscan wines during a one-hour Tuscan lecture at the Tuscan Wine School. Unlike traditional wine tastings, this experience is more educational, offering in-depth insights into Tuscany’s most important wines. Led by a local expert in a relaxed atmosphere, it’s a chance to absorb knowledge rather than just savoring sips. Delve into the history, legends, and techniques of Tuscan winemaking, gaining a profound understanding of the region’s wine culture. While it may not be your typical tasting, the lecture format ensures a comprehensive exploration of Tuscan wines, perfect for those seeking a more informative and intellectual wine experience.

Distance covered: 5mi (8km)

Meals included: Breakfast, Dinner

Today is free to rest any tired legs at the poolside. Alternatively, your leader can advise on local chianti wine-tasting tours, cooking classes, e-bike and vespa hire or offer assistance for unguided walks or daytrips.

Meals included: Breakfast

today is Florence, birthplace of the Italian Renaissance. Most of the greats from the movement lived or passed through here: Leonardo da Vinci, Michelangelo, Sandro Botticelli and more. Learn all about it by joining one of the free local tours, which typically take in the highlights.

Distance covered: 2mi (4km)

Meals included: Breakfast, Dinner

After a transfer to the quaint hamlet of San Donato, walk through farm grounds following the pathway to Montauto and on up to the medieval town of San Gimignano. The walk is not long and should take approximately three hours. The afternoon is spent exploring this beautiful town, including visits to the Palazzo Comunale, a 13th-century stone palace that’s home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa. There’s free time to wander and soak up the atmosphere. Before your farewell dinner, visit the family-run Cesani estate, which produces some of the finest wines in the region. Here you will enjoy an expertly led tasting, sampling your way through three glasses accompanied by bruschetta, extra-virgin olive oil and a selection of Tuscan cheeses and charcuterie.

Distance covered: 6mi (10km)

Meals included: Breakfast, Dinner

The trip ends after breakfast. Bid Hotel Le Renaie a fond farewell and begin your return journey home.

Meals included: Breakfast

  • Walk the classic rolling hills of Tuscany

  • Stay in a family run 3* hotel

  • Enjoy fabulous chianti wines

  • Visit Siena and Florence
Information
  • Seven nights in a 3* hotel with a swimming pool
  • Five days gentle walking and sightseeing
  • Low altitude throughout
  • Option to travel by train to your adventure
  • Option to book an extension package
  • Countries visited: Italy
     
What’s Included 
  • All breakfasts, five dinners, three wine tastings
  • All accommodation
  • All transport and listed activities
  • Tour leader throughout
People
  • Local guides keep you well informed about local traditions and cultural-social sensitivities.
  • This trip brings income and opportunity to the destination community through the inclusion of locally owned hotels, restaurants, and other enterprises, and by championing locally produced food wherever possible. Spend seven nights at the family-run Hotel Le Renaie near San Gimignano.
  • There will be three wine tastings, where you will learn about local wines and how they are made. This includes two sessions in local wineries and a short course at the Tuscan Wine School. These are great opportunities to support local suppliers and to encourage the traditional methods of local wine production.
Places
  • By travelling in a small group, you ‘tread lightly’ to minimise the impact on local resources and the environment.
  • Erosion on and adjacent to popular paths is a growing problem in certain places and therefore the trip leaders on this tour, will encourage clients to stick to advised routes to minimise this.

Gallery

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We are here to help. Our travel experts will organise and book your dream holiday.
call us today or complete our online enquiry form to start your next adventure.

Let's Chat

We are here to help. Our travel experts will organise and book your dream holiday.
call us today or complete our online enquiry form to start your next adventure.