Tuscan Villa Escape

8 day, 7 night
all-inclusive Tuscan Villa Vacation


On a Tuscan Escape you can expect sightseeing and farm visits, wine tasting at wineries, trekking and e-biking but also grand meals, pizza and picnics and plenty of wine.


See UNESCO World Heritage sites and famous wine regions but also explore lots of hidden Tuscany where the experiences and locals are most authentic.


Throughout your stay you will be passing time in a comfortable private and fully catered Villa and by the end, you will have connected with a new way of life, made new friends and created outstanding new memories to take home and share with everyone. 


Day 1 – Welcome with wine: Florence to Villa Transfer Tour via the Chianti

Explore the Chianti between the Provinces of Florence and Siena on this sight-seeing and wine tour between Florence and your Villa. Tour a hamlet and visit a family-run winery with guided visits of the cellars and enjoy a lunch with a pairing of the wines. Travel to the Villa and enjoy a Welcome dinner and event.

Arrive in Florence, meet the group at 11am and make your way to the first Chianti stop for sight-seeing. Enjoy a stroll through the typical historic hamlet and work up an appetite. Visit a family-run winery for a wholesome meal paired with the estate’s wines, and tour the vineyards and cellars for an introduction to the traditional production of wine in the area that has spanned the centuries. Following a scenic route, arrive at the Villa and explore the views. Rest or test the pool water before sitting down to a family style Italian meal with enough wine to make you forget your new travel buddies were ever strangers. Buon appetito!

Day 2 – Outdoor and hands-on fun: Truffle hunting and Villa cooking class

An active morning in the Tuscan countryside with a truffle hunter and his dog searching out truffles. Enjoy a hands-on cooking class to learn how to make fresh pasta and enjoy it with your fresh truffle shavings. Enjoy the pool, a group activity and dinner at the Villa.

After yoga and breakfast, we'll head out into the Tuscan countryside and follow a local hunter and his dog into the forest to search out the world’s most elusive mushroom, the underground truffle. Take in the forest smells and learn about the flora and edible plants and herbs. Return to the Villa with your truffles and forage and engage in a fun and hand-on preparation of a Tuscan meal. The cooking class will teach you how to make fresh pasta, which you can enjoy dressed with freshly-shaved truffles, as well as the simplicity of Italian cuisine. Rest or lounge around the pool and engage in an optional group activity that will finish in time for a delicious group dinner at the Villa.

Day 3 - See the colors – Painting Class & Siena Tour

Enjoy a creative morning painting a watercolor with the aid of a local artist, focusing on the unique colors of the Tuscan countryside. Enjoy a meal before exploring the many sights in Siena’s city center on a guided tour that will unravel its history and traditions. Enjoy some leisure time before spending the evening over an Aperitivo dinner of selected wines and delicious bites at the Tuscan Wine School.

Wake up and stretch those yoga positions until you smell the espresso. After breakfast, we'll try our hand at watercolor painting with a local artist. Learn the moves and depict the landscapes and colors that charm all visitors to Tuscany. After a wholesome lunch at the Villa, we drive out to Siena to enjoy a guided tour of the main sights of this majestic city, learning about its unique history and traditions. Discover the importance of the Palio, Siena’s medieval horserace, as you marvel the city’s main square. Follow your guide down secondary routes and get to know some of Siena’s secret corners. Enjoy some leisure time wandering the tiny streets, exploring the squares and medieval architecture or browsing the many shops of local products and crafts. Rendezvous at the Tuscan Wine School for an Italian Aperitivo dinner with a selection of local vino and delicious bites as the buildings begin to glow in the sunset light.

Day 4 – Stretching those legs in the Chianti: E-Bikes and Wine

Another active morning exploring secondary roads along Chianti’s vineyards, olive groves and shaded forests on the back of your E-bike adjusted to your level of difficulty, and follow your expert guide to a well-earned farm lunch. Be transferred to a family-run winery to learn all about the phases of production behind one of the world’s most renown and delicious wines: Chianti Classico. Return to your Villa for rest and restore your senses with an apertivo overlooking stunning views while eating hot pizza straight from a wood oven.

Head out to enjoy Tuscany’s stunning landscapes and sweeping views on a modern, assisted E-bike in the company of your experienced guide. Before heading off, familiarize yourself with the E-Bikes and equipment, which make biking in one of the world’s most famous cycling areas accessible to all! Easily set the difficulty of your ride and decide whether you would like the bike to do most of the work, or do the workout yourself. The silent electric motor allows you to enjoy the smells, sounds and tranquility of the Tuscan countryside throughout the 3 hour ride across neat rows of vineyards, olive groves, shaded forests, and sleepy villages. Stop to take in the views, take a picture and breathe the fresh Chianti air. Sit down to a wholesome farm meal and then visit a family run Chianti winery to learn all about all the phases of work behind the production of one of the world’s most renown and delicious wines: Chianti Classico. Return to the Villa for rest and be restored by an aperitivo overlooking stunning views and eat hot pizza straight from a wood oven.

Day 5 – Val d’Orcia, the UNESCO Valley: Pecorino Cheese and Brunello Wine

Set out on one of Tuscany’s most scenic routes across the UNESCO protected val d’Orcia and capture iconic landscapes. Visit an organic farm, see the animals and cheese laboratory and enjoy a tasting of the estate’s pecorino sheep cheese. Travel to the city of Pienza and learn about the Renaissance values that shaped it, enjoying some leisure time to explore its beauty and shops. Later in the afternoon, visit the nearby hill of Montalcino and meet producers of the famous Brunello wine. Tour the family-run vineyards and cellars and see the passion and patience behind these fascinating wines. Group dinner at the Villa.

After breakfast, make sure to take your camera as today we will follow one of Tuscany’s most scenic routes through stunning, landscapes and you will want to capture some iconic views. Soft rolling hills, solitary cypress trees and neat parcels of land shaped by man over the ages to create a harmony that even nature can’t beat. Tour an organic farm, say hello to the farm animals and see the bounty and variety that nature has to offer. Enjoy a guided visit of the cheese laboratory before sitting down to enjoy a goat and pecorino sheep cheese tasting. Enjoy a guided visit of the val d’Orcia’s jewel, Pienza, a town built by the humanist Pope Pius II embodying the philosophical and aesthetic values of the Renaissance. Wander the small streets, marvel and the grand architecture and enjoy sweeping views. Enjoy leisure time for lunch, shopping, or drink coffee and eat gelato while watching the world go by. In the afternoon, travel to the nearby Montalcino hill for an in-depth visit to a family run winery and see the passion and patience behind the fascinating Brunello wine. Enjoy a guided tasting of Rosso and Brunello with the producers and walk the streets of Montalcino, Siena’s last stronghold before losing its independence. Enjoy the scenic drive back to the Villa and enjoy a lovely dinner with the group.

Day 6 – Step back in time: Trekking Francigena and Vernaccia Wine

Guided tour of San Gimignano and its unique, UNESCO protected tower houses before exploring the surrounding countryside in the footsteps of pilgrims and your trekking guide. Learn more about the rise and fall of trade, crafts and agricultural activity in and around San Gimignano and soak in the timeless values and beauty over an open-air picnic lunch. Tour a family-owned winery to learn about the historic Vernaccia wine, the only DOCG white wine of Tuscany and enjoy a guided tasting in the presence of the producers. Return to your Villa for a delicious evening meal.

Enjoy a guided tour of San Gimignano in the shade of its tower houses before the day’s bustle begins, taking many steps back in history among the cobble stone streets in town, through the squares and onto the fortress. Hear about the rise, fall and revival of the ancient pilgrim’s route, the Via Francigena, with its history and connection to the trading and crafts within the city walls and the agricultural activity in its surroundings. Follow in the steps of pilgrims, and your trekking guide, to enjoy secondary routes lined with cypress trees, vineyards and olive groves. San Gimignano and the surrounding landscape are both UNESCO protected world heritage sites, expressions of timeless values and beauty, the perfect backdrop to an open-air picnic lunch. Explore this wine growing region further by visiting a family-run winery to taste Tuscany’s only DOCG white wine and one of Italy’s most historic wines, the Vernaccia di San Gimignano. After a guided tour and tasting,

Day 7 – Feel the pride: Montepulciano, Sunset Dinner

A slow morning and early Villa lunch before setting out to see the Crete Senesi, the rolling clay hills of Siena, and to learn about the liquid gold of the area, extra virgin olive oil. Continue to the proud old town of Montepulciano to wander its many streets, churches and palazzo and to indulge in a cellar tour and tasting of the Vino Nobile wine that is still made by noble families today. After some leisure time, return to the Chianti to enjoy a farewell, sunset dinner on a Chianti winery that has been passed down through generations, in the company of the estate’s best wines of course

Enjoy a slow morning and savor a lunch in Villa before driving out, today you’ll see the rolling clay hills of the Crete Senesi to the south east of Siena and learn about the precious liquid gold of the area, extra virgin olive oil. This labor-intensive staple preserves food and is a delicious and healthy dressing that is fascinating and often poorly understood. Learn about the different olive cultivars and enjoy a tasting of different, mild and spicy olive oils and continue to the proud town of Montepulciano. This city that is perched on the hill with its large churches and squares boasts some of the most elegant palazzi and we will visit an ancient wine cellar right in its center. Learn about this particular Sangiovese and taste the Vino Nobile that is still made by noble families in this old town.

Enjoy leisure time wandering the squares, churches and many craft shops before returning towards the Chianti for a guided tour of a family-run farm that has been passed down over many generations. Explore the estate’s gardens and wine cellars before sitting down to a charming farewell dinner in the company of the changing sunset colors and the farm’s best wines.

Day 8 – Farewell: Transfer back to Florence

A last breakfast at the Villa and return to Florence connected with a new way of life, having made new friends and created new memories to take home and share with everyone.

18 -26 September 2021



Per Person in double room


Available as private itinerary for a minimum of 6 or for group with own villa (with private kitchen) 


Where You Will Stay

Comfortable Tuscan Villa in with private pool, and garden.

Picture is only indicative of standards. All the Villas we use are with private bathrooms and communal kitchen, eating area and outdoor space, including pool.

What’s Included

  • 7 Nights in fully serviced Tuscan Villa

  • Comfortable minivan transportation for all activities

  • Yoga and breakfast

  • Lunches and dinners: all meals except one

  • Cooking class

  • Truffle hunting

  • Painting class

  • Chianti E-Bike Tour

  • Private walking tour of Siena and San Gimignano

  • Guided visits of Monteriggioni, Pienza, Montalcino and Montepulciano

  • Via Francigena Trekking

  • Organic dairy farm tour and tasting

  • Cellar tours and tastings of Chianti, Vernaccia, Brunello and Nobile wines

  • Rooftop aperitivo

  • Local trip leaders throughout the trip

  • Insider knowledge

Book Your Tuscan Escape
Shared dates (maximum 8 persons)
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