Chianti Walking Tour Header

Chianti Walking & Wine

About This Walk

Discover Picturesque Towns & Delicious Wines In Tuscany

With its Renaissance cities, medieval villages and cypress-lined avenues snaking through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the tranquil Villa Casalta, on our tour we visit beautiful San Gimignano, the market town of Greve in Chianti, the UNESCO World Heritage Site of Siena and the magnificent city of Florence. During the week we sample several varieties of the world-renowned local Chianti and have the opportunity to learn more about Italian wine at the Wine School of Siena.

Highlights

  • Walk the classic rolling hills of Tuscany
  • Stay in a converted farmhouse
  • Enjoy the fabulous Chianti wines
Uwalk Difficulty Icon One
Uwalk Difficulty Icon One
Uwalk Difficulty Icon Two
Uwalk Difficulty Icon Two
Dublin to Tuscany
7 Nights
€1205 pp

Day 1: Start Castellina in Chianti

Start at Villa Casalta, our beautiful villa 2km from Castellina in Chianti. In the evening our guide will hold a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.

Meals included: Dinner

Day 2:

Visit mediaeval market town of Greve in Chianti and the hilltop village of Montefioralle; afternoon wine tasting in Castellina.

Today we head to the mediaeval market town of Greve in Chianti walking through a magnificent setting of olive groves and vineyards. On the way, we will stop in the fortified hilltop village of Montefioralle, considered the most ancient ‘borgo’ in Chianti. After lunch we enjoy a wine tasting in a local winery before heading back to our farmhouse for dinner.

Meals included: Breakfast, Dinner

Day 3:

Walk to Radda in Chianti, the heart of the Chianti area.

This morning we will set out for a local history walk to the heart of the Chianti area, covering the route from Villa Casalta to Radda in Chianti. We will take a walk through local woodlands where we can admire the so famous emerald vineyards valleys. In the afternoon we will have the chance to taste the much acclaimed Chianti Classico wine at a local winery.

Meals included: Breakfast

Day 4:

Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at the Wine School

After breakfast we make our way to the centre of Siena for a day exploring this fascinating city. We have time to visit the numerous museums and stunning Duomo and to relax in one of the many outdoor cafés in Piazza del Campo, home of the world famous Palio horse race. Please note that shoulders should be covered for entering the Duomo. You may also like to visit the many boutiques specializing in local products and cutting edge Italian fashion. In the afternoon we also have the opportunity to learn about Tuscan wines on a 1-hour fun interactive course at the Tuscan Wine School.

Meals included: Breakfast, Dinner

Day 5:

Free day to visit other Chianti villages or relax by the pool

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

Meals included: Breakfast

Day 6:

Discover the magnificent city of Florence, considered the birthplace of the Renaissance

Our destination today is the magnificent city of Florence, the birthplace of the Italian Renaissance with an enormous wealth of historical sites, museums, galleries, churches and architectural delights. Most of the great artists, thinkers and builders from Renaissance history passed through or lived in Florence when it was under the rule of the Medici family, the most famous patrons of the 16th century. But Florence is not just a Renaissance showpiece: once you have had your fill of the historical trail there are many other things to see and do. The city has not ceased to be a centre of learning, and there is a university, many art and language schools and a large student population to liven up the café-bars, restaurants and nightclubs. There are also some great markets and chic boutiques. From April to July, Florence also holds one of Europe’s major cultural events, a festival of opera and classical music called the Maggio Musicale Fiorentino.

Meals included: Breakfast, Dinner

Day 7:

Walk to picturesque San Gimignano with free time to explore Palazzo Comunale, Pinacoteca and Torre Grossa

After a transfer to the quaint hamlet of San Donato, we walk through the farm grounds following the pathway to Montauto and on up to the picturesque medieval town of San Gimignano. The walk is not long and should take approximately 3 hours. The afternoon is spent exploring this beautiful town including visits to the Palazzo Comunale, Pinacoteca and Torre Grossa and there is some free time to wander and soak up the atmosphere.

Meals included: Breakfast, Dinner

Our price of from €1205 per person departing Jun 15th – Flights Extra

  • 7 nights renovated farmhouse with panoramic swimming pool
  • 5 days gentle walking and sightseeing
  • Low altitude throughout
  • Centre-based holiday
  • All breakfasts, 5 dinners, 3 wine tastings
  • All accommodation
  • All transport and listed activities
  • Tour leader throughout

 

Not Included

  • Travel insurance
  • Single accommodation (available on request)
  • Visas or vaccinations
  • Local taxes

Tdc

Villa Casalta

You will spend 7 nights at Villa Casalta, a renovated farmhouse with swimming pool and en suite facilities. The villa is family-run and known for the fine home-made food prepared with traditional ingredients and locally produced wines and olive oil. Free Wi-Fi available.

Are you interested in this tour?

We're here to help!

Related Tours