Siena, Italy

Come for the adventure. Return with more of yourself.

Each summer, Siena becomes the stage for one of the world’s most extraordinary living traditions: the Palio di Siena. This WiseWell Adventure offers rare insider access to the civic, emotional, and spiritual life surrounding the race, made possible through a family whose ties to the Palio run deep. Held between the charged beauty of Siena and the quiet grandeur of a private Tuscan castle, the journey balances pageantry, belonging, and wonder with restorative comfort, movement, and reflection.

Top 8 Highlights

Stay in a private family castle in the Tuscan countryside
Insider access to the world of the Palio through a family deeply woven into its history
Viewing the Palio from a private window in catered comfort
Experiencing the Palio with commentary from a 13x winning Palio jockey.
Witnessing the trial races and the horse selection ceremony
Attendance at the Blessing of the Horses
Coveted invitation to Contrada dinner during Palio week
Wine tastings in the estate vineyard and extraordinary Tuscan dinners
Horseback riding, e-bike excursions, private massage, and WiseWell practices

Signature

experiences

of the journey

This retreat offers rare insider access to the world of the Palio through hosts whose lives are deeply entwined with its history and traditions.

The defining moment is viewing the race itself from a coveted private window overlooking Piazza del Campo, accompanied by a 13-time Palio winner whose real-time insight brings extraordinary depth, emotion, and understanding to one of Italy’s most thrilling, storied, and culturally significant living traditions, making the experience unforgettable for every guest.

Beyond the Palio itself, the journey unfolds through the beauty, intimacy, and living traditions of Siena and the Tuscan countryside. Guests stay in a magnificent private castle held by the same family for centuries, witness the charged trial races and emotional horse selection ceremony, and attend the Blessing of the Horses, one of Palio week’s most moving rituals. A coveted Contrada dinner offers rare entry into Siena’s social fabric, while conversations with a legendary Palio family, including the only female jockey currently riding, deepen the sense of access and context. Wine tastings in the estate vineyard, remarkable dinners beneath the Tuscan sky, horseback riding, guided e-bike excursions, canoeing, a private in-room massage, and Susan Wise’s signature movement and reflection practices complete the experience. The result is a journey of pageantry, belonging, restoration, and rare cultural privilege, held in an atmosphere of beauty and care.

WiseWell philosophy paragraph relating to this adventure

WiseWell creates journeys that balance wonder with grounding, and cultural immersion with restoration. In Siena, guests move between ritual intensity and deep comfort, experiencing history not as spectacle, but as something shared and renewing.

Ideal
Guest

This journey is designed for travelers who are drawn to history, ritual, belonging, and extraordinary cultural access. It is especially suited to those who want more than a spectator experience – guests who value intimacy, tradition, and the rare privilege of being welcomed inside a world few outsiders ever truly encounter.

Together, these experiences create something far richer than a vacation—they offer a true invitation into the heart and soul of San Miguel de Allende. An invitation to travel fully alive.

What's included?

Your Living Lineage brings together a rare convergence of moments: a front-row seat at the Copa Vendemia polo tournament, an exclusive Santa Catrina dinner with polo players and sponsors beneath the vines of San Lucas vineyard, thermal baths, sound healing, and the quiet magic of San Miguel de Allende’s cobblestone streets — all woven through with something most luxury travel never offers: the space to actually exhale.

We begin with a lively welcome dinner that doubles as a cooking class led by a Mexican-born, French-trained chef—an easy, laughter-filled evening designed to bring everyone together over extraordinary food.

Each morning, Susan leads her signature sessions blending conversation, reflection, and gentle movement to awaken presence, joy, and self-awareness.

Our days include a private sound healing at extraordinary thermal baths, a leisurely vineyard lunch overlooking a tranquil lagoon, guided historic stroll through San Miguel’s historic center, and in-house massages.

One evening we gather for dinner at a rooftop restaurant overlooking the Parroquia before enjoying live music nearby.

Beautiful surroundings, thoughtful experiences, and shared laughter make this a retreat for both heart and spirit.

Your investment includes transportation, accommodations, meals, activities, and materials.