Your Retreat to Tuscany Signature Sample Itinerary


Saturday – Arrival Day!

  • ARRIVAL and transfer to Villa Maddalena in the village of Montisi (2.5 hours north of Rome and 1.5 hours south of Florence)
  • Welcome reception and casual dinner at Villa Maddalena
  • Free evening to settle into your Villa, stroll the village of Montisi and get acquainted with your group
    You will quickly relax into the Tuscan way of life.





  • Breakfast and casual morning
  • Walking tour of your new village for a week, Montisi. Get oriented with the town, learn about the rich culture and landscape of this little village. Meet some of the locals, and take in the amazing views.
  • Return to the Villa for lunch
  • Enjoy the grounds, the pool, settle into slowing down
  • Afternoon guided painting experience – create your own painting of the beautiful Tuscan landscape and create a memory you can take home and enjoy for years to come! Social hour at the Villa before dinner
  • Group Dinner at Villa Maddelena



  • Morning intentions, meditation/yoga offering, Breakfast
  • A custom tour with the family of renowned Olive Orchard Olivera Sant’ Angelou and sample their delicious olive oil
  • Private guided Tour of Montepulciano – walking tour of the medieval village, a visit to the Etruscan tombs and winery in the underground caves, including a private wine tasting experience
  • Wander through the winding, narrow cobblestone passages and explore the history of copper making, leather goods, and Tuscan treasures! (on your own for lunch and shopping).
  • Late afternoon free time to relax, rest, enjoy the villa
  • Group Dinner at La Romita in Montisi




  • Breakfast and casual morning at the villa 
  • Do like the locals do and take in the morning at the market in the nearby town of Sinalunga. Shop for local goods, food items, and clothing and enjoy a cappuccino with your pastry in the piazza while you people watch and savor the delights of the local market.
  •  Drive to the charming town of Cortona (where Under the Tuscan Sun was filmed!)  Shop, walk, sample the local fare, people watch, sightsee the pristine village on the top of the hill. Return to villa.
  • Group Dinner at Villa Maddalena



  • Morning intentions, meditation/yoga offering, Breakfast & mid-week check-inPodere il Casale
  • A full culinary day at a private family-owned farm! This organic farm-to-table experience at Podere il Casale includes a cooking class making hand-rolled pasta, a classic Italian-style pork tenderloin and traditional tiramisu!
    The fruits of your labor will be enjoyed as you savor your prepared meal and conclude with a cheese demonstration. Also included is a tasting and education of the winery’s organic wines, produced on site. Free time to walk the property, meet the farm animals that produce the phenomenal cuisine, and savor the incredible views of the Tuscan hillside while you relax and enjoy your beautiful meal. Return to Villa
  • Free time at the villa
  • Lite Dinner and casual evening at Villa Maddalena



  • Breakfast and casual morning at the villa
  • SIENA: Guided tour of the Cultural city of Sienna – visit the Piazza del Campo, where the famous Palio horse race takes place, and see masterpieces by Michelangelo, Donatello, Bernini and others, as you learn about the rich history, art and treasures of the heart of Tuscany. Lunch on your own in Siena
  • Free time at the Villa
  • Group dinner at Villa Maddalena





  • Morning intentions, meditation/yoga offering, Breakfast
  • A decadent and relaxing day in the medieval village of Bagno Vignoni. This is a special day to help you wind down your week; Lounge in the thermal pools or on your private chaise lounge and enjoy a leisurely afternoon “Italian-style” in this modern, decadent oasis of natural mineral baths. While there, treat yourself to a spa service or simply relax and savor the gorgeous views and the warmth of the sun and the pools (on your own for lunch – there are lovely options for food and drinks for purchase in town and at the pools)
  • Free time at the villa to organize, pack and relax
  • Departure Dinner and Celebration at Villa Maddalena


Saturday – Departure

  • Breakfast, sweet goodbyes, and departures – Ciao Ciao e viaggi sicuri!

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