The Best of Classic Tuscany

Visit charming medieval villages, walk in ancient countryside fields and forests all while indulging in divine meals, wines and gourmet products that make this region so famous. We will indulge your senses while providing you with exceptional countryside accommodations, showing you the most stunning parts of Tuscan nature all the while enjoying delicious and decadent food.

This package includes:

• Transfer from Florence or Siena to countryside villa where you will spend the next 6 nights
• A light welcome lunch the first day
• 5 walking excursions, ranging between 6km and 15km
• Two wine and olive oil tastings
• Italian Buffet Breakfast for 6 days
• Typical Tuscan dinner each night
• Transfer from the Villa to Florence Airport or Station

See below for the day-by-day tour description:Length: 7 days, 6 nights

When: Available Year Round

Meeting Point: Our Offices in Via Sassetti, 1 Florence Italy

Includes: See below

Weather: April-October 64-86°F (18-30°C)

Notes: You must be fit and healthy to do this tour. Proper and comfortable walking shoes/light hiking shoes are required for walks.

Day 1: 
We will meet you in the morning in Florence and provide private transportation to our accommodations San Quirico d’Orcia, a charming medieval village in southern Tuscany. After check-in, you will be able to enjoy a light welcome lunch, followed by an lovely stroll in the center of this quaint and picturesque medieval village. From here, you will travel to the equally beautiful Cappella di Vitaleta and begin your first excursion into the stunning Val d’Orcia countryside. You will first visit the ancient borgo of Pieve di Corsignano and then make your way towards the village of Pienza. Here you will be able to admire perfect renaissance architecture hidden away in this small medieval village known for its wonderful Formaggio di Pecorino Fresco – fresh sheep’s milk cheese. After returning to San Quirico you will be able to enjoy free time before dining in one of the village’s the typical restaurants. 

Distance covered on walk: 6 km

Length: 2 hours

Exertion level: minimum

Terrain: dirt roads and some secondary paved (sealed) roads

Shadow: Sufficient shadowing

Height: maximum 491 m, minimum 300m

Day 2:
After enjoying a sumptuous breakfast before, you will make your way towards Rocco a Tentennano. Along the journey, immersed in the Tuscan countryside, you will stop in the medieval village of Vignoni. From Vignoni, you will then arrive at the famous Bagni Vignone, an ancient geothermal area. Famous for centuries, this well-known region dates back to the Etruscans boasting healing waters in its natural baths, fountains and pools. After exploring the baths, your excursion continues along the Orcia river and winds through streams, fields and old farm houses finally arriving at the village of Rocca d’Orcia. This breathtaking medieval town is perched on top of a rocky ridge and boasts an incredible panorama of the surrounding countryside and rolling hills topped with cypress trees. Here you can finally take in all of the surroundings while enjoying a sack lunch – no better way to tantalize all of your senses! Having regained your energy the excursion continues on to another stunning jewel: Radicofani. Here you will marvel at the 16^th century fortress and stunning castle with an equally breathtaking view over the astonishing valleys and hills that make up this part of Tuscany: a 360°degree view including Val d’Orcia, Val di Paglia, Monte Amiata and even Siena. After your second spectacular day, you will enjoy free time before another mouthwatering dinner.

Distance covered on walk: 10 km

Length: 3.5 hours

Exertion level: medium/high

Terrain: dirt roads and forest paths

Shadow: some shadowing

Height: maximum 550 m, minimum 250m

Day 3:
After enjoying an energizing breakfast, you will travel to Pienza from where today’s excursion begins. After walking through the delightful historic center, you will begin the walk from outside the city’s walls taking a dirt path leading away from the city. Along the way, you will be overwhelmed by the surrounding countyside; enjoying views of fields coming to life with wildflowers. This beautiful journey will lead you into the medieval borgo of Monticchiello where you can continue to explore this little medieval jewel. After relaxing in Monticchiello your excursion continues into a shaded thicket through which the Tresa river runs. You will explore through this area and arrive at the ancient temple of San Biagio which lies at the foot of Montepulciano. After a well-deserved and hearty lunch in Montepulciano, you will be able to explore the many shops, wine cellars and other hidden treasures in Montepulciano. You will not want to miss the wonderful assaggi or tastings that both the Redi and the Avignonesi wine cellars have to offer! In the early evening, you will return to San Quirico and enjoy a another delicious meal to restore your senses.

Distance covered on walk: 15 km

Length: 5 hours

Exertion level: high

Terrain: dirt roads and forest paths

Shadow: some shadowing

Height: maximum 550 m, minimum 305m

Day 4:
Today you will enjoy some respite from your excursions and take a wonderful day trip to two authentic Tuscan jewels: Siena and San Gimignano. After your breakfast buffet, you will travel first to San Gimignano and visit many of its original medieval towers (over 10 or the original 70 are still standing!) Strolling through the windy, medieval streets you will discover the hidden gems that make San Gimignano so unique; ceramics, leather goods, and original medieval and renaissance architecture. You will thoroughly enjoy a typical lunch including local wines such as the famous Vernaccia white wine and the red Chianti Colli Sienesi at a family owned farm and wine producing estate. We will say goodbye to our friends on the farm and make your way towards Siena where you will continue your day exploring the hills and hidden streets in this ancient walled city. You will also enjoy free time on your own exploring and then in the evening, meet for an aperitivo to whet your appetite in the city’s famous oval Piazza del Campo. We will dine in Siena and enjoy a typical Sienese meal before returning to your hotel for the evening.

If you prefer to visit areas in Tuscany, other than Siena and San Gimignano the guide can arrange an infinite number of alternatives.

Day 5:
Our fifth day begins with a morning excursion to the Abbey of Sant’Antimo where you can visit this famous religious setting beforing beginning today’s walking excursion. You will walk along the Via Francigena which during the 9^th century ran through Italy connecting it to France. Walking along this ancient pathway you will share steps with the many pilgrims who passed along on the same road taking shelter in the same shaded olive groves and forests. After passing through Passo del Lume Spento and through various Estruscan habitations you will finally reach the walled city of Montalcino. Upon arrival in Montalcino you will be able to sit down to a restoring lunch and then visit this beautiful and charming city so well-known for its red wine, Rosso di Montalcino. Later on, you will be able to taste, first hand, the most famous wine Montalcino produces, the prestigious Brunello di Montalcino in the historic farm of Collosorbo. In the evening, you will return home to dine in Rocca d’Orcia.

Distance covered on walk: 10 km

Length: 3.5 hours

Exertion level: high

Terrain: dirt roads and narrow forest paths

Shadow: some shadowing

Height: maximum 550 m, minimum 305m

Day 6:
Our last day together is spent visiting the Abbey of Monte Oliveto Maggiore, its famous fresco paintings and, natural healing pharmacy with products produced by the Abbey and run exclusively by the monks living there. After your visit, you will proceed to the ancient borgo of Chiusure then heading on to Buonconvento located in the middle of the famous Creti Senesi, the famous hills surrounding the area outside of Siena. These amazing countryside views will take your breath away as you travel by foot to reach the interior of Buonconvento where you will dine at a local, family-owned trattoria. After your restorative lunch, you will go on to visit Murlo and its amazing Etruscan museum which includes the archeological remains the Poggio Civitate. A panoramic drive home will heighten your senses to enjoy our final dinner together to celebrate our wonderful days of touring together!

Distance covered on walk: 10.5 km

Length: 3.5 hours

Exertion level: high

Terrain: dirt roads and narrow forest paths

Shadow: some shadowing

Height: maximum 410 m, minimum 145m

Day 7:
Departure day with private transfers from the villa to either Florence or Siena