Into the Wilds of Tuscany
Italy
October 1 - 8, 2026
Beyond the “Tourist Trail”
Adventuring in Europe is a dream come true, right? …
That is, unless you’re hurrying from site to site amongst crowds of tourists, waiting in long lines, and left longing for a deeper connection to Italy and its people.
That’s why we created Into the Wilds of Tuscany! — a 7-night bespoke adventure that takes you off the beaten path and into the heart and soul of Italy’s Siena Province.
Every aspect of this adventure is designed to help you slow down, breathe deeply, and experience the kind-hearted people, age-old traditions, delicious cuisine, and iconic landscape of this region.
Live well, savor precious moments, and fully celebrate your life.
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THE EXPERIENCE
Awaken each day with invigorating practices, including qigong, walks, breathwork, meditation, and yoga on a private deck overlooking the Tuscan countryside or inside our yoga shala. Stargaze from the wood-fired hot tub. Enjoy a glass of Italian wine by the fire. Immerse in a symphony of flavors at every meal, where every bite is not only nourishing but takes you on a sensory journey to the heart of Italy.
Savor inspiring discussions where we cultivate a powerful container for reflecting, sharing, and moving toward clarity about what’s truly important to us.
We spend our days exploring and diving deep into this incredible place and its people. Because of our deep relationships with our in-country partners, you’ll be welcomed into magical spaces and settings that visitors typically won’t experience. Expect to leave Italy with a new sense of home.
What to expect:
- Daily mindful movement and practices designed to connect you with your body and breath (No fitness or yoga experience necessary. All levels. Beginners welcome!).
- Time spent in nature, featuring walks through the picturesque countryside and the soothing experience of stargazing from a wood-fired hot tub.
- Engaging discussions that foster reflection and clarity on personal values and what truly matters, creating a supportive and inspiring environment for all participants.
- Exploration of iconic locations, including visits to local artisanal grape and olive vineyards tended by the same families for generations, pre-Roman villages, and other historic sites, including the world-class city of Siena. You’ll enjoy a scenic e-bike cruise through the Italian countryside and an afternoon bathing in mineral-rich thermal pools.
- Culinary delights featuring nourishing meals prepared with fresh, local ingredients (All meals and snacks are included).
- Daily grounding practices like meditation, soundbath, and breath techniques to invite relaxation and inner rest.
- Plenty of downtime for reflection and connection.
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THE DESTINATION
Our home away from home, The Roccone, is the name of the rock bluff upon which a legacy farmhouse has overlooked a lush valley for over 150 years. This sprawling 321-acre property is located at the center of what is now the Pigelleto Nature Reserve, just two hours outside Rome.
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THE PROMISE
Slip into the gentle rhythms of the Italian countryside. Together, we’ll immerse ourselves in the beauty of Italy while discovering what it means to cultivate ease, balance, and joy in our lives. You’ll immerse yourself in daily yoga and movement, mindful meditation, time in nature, nourishing meals, and curated cultural experiences.
This intimate adventure invites you to slow down, savor simple pleasures, and reconnect with yourself, one heartfelt moment at a time.
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LODGING
Every detail of our private retreat, right down to the centuries-old stone pizza oven, offers a refined, rustic elegance. Fully renovated in 2014, this private estate offers a large, well-appointed shared bedroom with shared bathrooms; a spacious dining room; a comfortable living room and kitchen; a private yoga shala and meditation platform; walking trails; a wood-fired hot tub; and panoramic views.
Accommodation options include private (single) or shared (double) rooms with shared bath.
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BOOKING DETAILS
8 days / 7 nights lodging at a refined farm estate blending modern comforts with historic charm.
Shared double queen room with shared bath - $4922
Private king room with shared bath - $5435
A non-refundable deposit is required to secure your booking. Balance is due 30 days prior to the start date. All prices are PER PERSON.
Changes/Cancellations
We understand that plans can change and emergencies come up. However, due to the nature of our services, we have a strict no-refund policy.
No Refunds: all bookings are final, and no refunds will be issued for cancellations or changes. This includes family, health, death, and other emergency situations. Registrations are transferable.
Travel Insurance: To protect your investment, travel insurance is strongly encouraged (and easy to get!) to cover unexpected cancellations, delays, or other unforeseen circumstances.
What's Included:
- Seven nights accommodation
- All meals, beverages and snacks
- Daily yoga, movement, and wellness classes, workshops, and seminars .
- Daily excursions and activities
- Ground transportation between our retreat venue and Rome.
- Ground transportation for all excursions and activities.
- Pre and post-retreat concierge services from our team
- Wifi
- Laundry service
- One massage
What's Not Included
- Air Travel
- Travel Insurance
- Staff or third-party gratuities
- Outside food or beverages
- Additional transportation outside designated ground transportation windows
Additional Information:
Ground transportation to and from Rome will depart at a set time. We recommend you book flights to arrive in Rome at least 1 day before / depart at least 1 day after the retreat to account for potential delays and a relaxed arrival and departure schedule.
If you would like hotel or travel suggestions in Italy before or after your retreat, we would be happy to assist you!
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LEADERSHIP
This adventure is designed and led by Molly Casto and Lauren Dunne, Co-Creators of On Point Adventures.
