tuscan cities II

4 nights from £780 per person

Another lovely city break designed to bring together a small group of friends who wish to experience this beautiful region in luxury.  You will be collected from the airport, transported to Casa Leana and then each day of your stay you will be chauffeured to three of Tuscany’s most beautiful cities.  And in the evenings visit some of our favourite local restaurants and bars, not forgetting an in house four course Tuscan feast cooked for you by our neighour and a trip in our iconic Fiat 500.

to set the scene

Our lovely old farmhouse will be handed over to you for the duration of your stay for your exclusive use but don’t worry we only live a couple of kilometres away so will be on hand should you need anything and Leigh will be your driver.

You’ll love the welcome hamper full of goodies plus 4 bottles of locally produced wine compliments of Casa Leana.

No trip to Italy is complete without a Fiat 500 experience. Our tiny car is so iconic that driving around in it attracts as much attention as a minor celebrity and with your very own chauffeur driving you into town one evening you will certainly feel like one!

Day 1 Saturday

Collection from Florence or Pisa Airport and onwards to Casa Leana for a relaxing afternoon around the heated swimming pool.  A trip into town in the Fiat is in order this evening to a wonderful trattoria with fabulous views of the valley. 




  • Relax around the pool

  • Visit to local restaurant

  • Fiat 500 Experience

Day 2 Sunday

Today we are off to Tuscany’s capital city of Florence.  Few cities are so compact in size or so crammed with extraordinary art and architecture masterpieces at every turn. The urban fabric of this small city, on the banks of the Arno river, has hardly changed since the Renaissance and its narrow cobbled streets are filled with elegant 15th and 16th century palaces, medieval candle-lit chapels, fresco-decorated churches, marble basilicas and world-class art museums brimming with paintings and sculptures by Botticcelli and Michelangelo. Unsurprisingly, the entire city centre is a Unesco World Heritage site.  A visit to the famous Uffizzi Gallery, home to the world's greatest collection of Italian Renaissance art, is included in this wonderful day out followed by a long lazy lunch in one of our favourite city restaurants. 

Back to Casa Leana for a typical Tuscan meal cooked from scratch by our lovely Italian neighbour.


  • Visit to the Uffizzi Art Gallery

  • Lunch in Florence

  • Home cooked Tuscan meal cooked by a local and served in the Casa Leana kitchen

Day 3 Monday


Today we will be visiting Montepulciano. Exploring this medieval town, which is perched on a reclaimed narrow ridge of volcanic rock, will push your quadriceps to failure point but don’t worry there are plenty of little wine and cheese tasting shops along the way to keep you going.  Close to the top we plan to stop off for lunch accompanied by a few glasses of wine in one of our favourite spots taking in the spectacular views over the Val di Chiana and Val d'Orcia. 


Back home to Casa Leana for an evening meal in one of the beautiful medieval towns that surround us in a wonderful little trattoria.


  • Visit to Montepulciano

  • Wine and cheese tastings

  • Lazy lunch

  • Evening meal among the olive trees

Day 4 Tuesday

Today we visit Cortona, one of our favourite places.  Although it is small – it's perfectly formed!  It is a town full of swanky little boutiques, cafes and restaurants.  Cortona is enclosed by stone walls and is about 600 metres above sea level which makes for spectacular views of the surrounding valley and the beautiful Lake Trasimeno. Here you can visit the beautiful Santa Margherita Sanctuary plus the Girifalco Fortress.  During the day we will be stopping off for refreshments in lovely little cafés and lunch in one of our favourite restaurants.  Back over the valley home to Casa Leana for an evening meal in a little family run pizzeria




  • Visit to Cortona

  • Santa Margherita Sanctuary

  • Girifalco Fortress

  • Lunch in a fabulous restaurant

  • Visit to Anghiari for evening meal

Day 5 Wednesday

Collection from Casa Leana for your transfer back to Florence or Pisa Airport.​

What's included in the price

Airport transfers in Italy

4 nights accommodation

Welcome hamper including 4 bottles of wine

Day trip to Florence

Day trip to Cortona

Day trip to Montepulciano

Wine tasting

Fiat 500 Experience

Breakfasts, Lunches and Evening Meals

1 bottle of house wine with lunch and dinner per day

Created by Leigh Wright & Diana Flanagan - Owners Casa Leana

Address: Barliano,  n°116 - 52031 Anghiari Ar                                                                              

Photography by Rob Moles

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