Keepers of Tradition & Culture in Travel

The Art of Tuscany Retreat: Florence & Val d’Orcia

Life Beyond the Room, in collaboration with Jennifer Young, brings you a retreat in the Tuscan countryside.

7 days

This retreat is an invitation to experience Tuscany through creativity, craftsmanship, and a deeper connection to place. Moving from the artistic heart of Florence to the rolling landscapes of the Val d’Orcia, the journey reveals a region where beauty is not simply admired, but shaped by hand, cultivated through tradition, and woven into everyday life.

The experience begins in Florence, a city defined by imagination and human expression. Beyond its celebrated architecture and Renaissance masterpieces lies a quieter, more intimate world of artisans, workshops, markets, and family traditions. Guests explore the city through its flavors and stories, step behind the doors of working studios, and discover the skill, patience, and passion that continue to sustain Florentine craftsmanship.

Creativity becomes something tangible. A hands-on leather workshop offers the opportunity to learn from master artisans and create a personal piece using techniques passed down through generations. In the kitchen, seasonal ingredients become a way to understand Tuscan culture, as guests prepare traditional dishes together before gathering around the table to share what they have made.

From Florence, the journey moves into the countryside, pausing in Chianti for an intimate wine experience and farmhouse lunch before continuing toward the UNESCO-listed landscapes of the Val d’Orcia. Here, vineyards, olive groves, cypress-lined roads, and medieval villages create a natural rhythm that encourages guests to slow down and become fully present.

The days unfold through meaningful encounters with the land and the people who care for it. Guests cycle through the countryside, visit biodynamic vineyards, taste Brunello di Montalcino where it is produced, and discover how wine, olive oil, cheese, and ancient grains carry the identity of this remarkable region. A simple picnic overlooking the hills becomes as memorable as the most refined meal, reminding us that true luxury often lives in authenticity, beauty, and time shared well.

Throughout the retreat, thoughtful guidance and facilitation provide a steady sense of connection while leaving space for personal discovery, conversation, and reflection. Experiences are intentionally balanced with moments to wander, rest, and absorb the atmosphere, whether exploring the streets of Pienza, relaxing beside the vineyards, or watching the Tuscan light soften over the hills.

Evenings bring the group together around generous tables, where seasonal food, local wine, and unhurried conversation create a small and meaningful sense of community. As the journey progresses, the distinction between activity and reflection begins to fade: making, tasting, walking, and gathering all become part of the same deeper experience.

This retreat is designed for travelers who are drawn to the soul behind beautiful things. It is not simply about seeing Tuscany, but about engaging with its living traditions and understanding the human stories behind its art, food, and landscapes.

The result is a journey that feels both enriching and restorative, rooted in creativity, guided by intention, and shaped by the enduring beauty of Tuscany.

What’s Included?
  • 3 nights in boutique accommodations in Florence
  • 3 nights in boutique accommodations in Val d’Orcia countryside
  • All breakfasts, selected lunches and dinners
  • Guided sensorial walk and tastings through Florence
  • Guided artisan workshop tour in the Oltrarno district
  • Traditional Tuscan cooking class followed by dinner
  • Belt-making workshop at the historic "Scuola del Cuoio"
  • Exclusive Chianti winery experience and farmhouse lunch
  • Wine and e-bike experience through the Val d’Orcia countryside
  • Pecorino tasting and countryside picnic experience
  • Private airport and train station transfers
  • Private transfers between destinations and for all scheduled activities
  • Local expert guides in each destination
  • LBR onsite facilitator
  • International airfares
  • Gratuities
  • Alcoholic beverages not specified in the program
  • Additional excursions
  • Personal styling purchases and shopping expenses
  • A la Carte Spa Services

Meet Your Guide(s)

Jennifer Young

Jennifer Young is a personal stylist, speaker, and founder of Emerge by Jennifer, with more than 15 years of experience helping people use style as a powerful expression of identity, confidence, and personal growth. Drawing on a diverse career spanning the stage, corporate leadership, human-centered design, and fashion, she created the signature Style by Design™ Framework to help clients align their story, style, and presence. For this retreat, Jennifer brings her thoughtful and deeply personal approach to Tuscany, guiding guests through an exploration of creativity, craftsmanship, and self-expression while creating space to reconnect with who they are and who they are becoming.

Departures Available
October 17-23, 2027
Starting at
8.000
Single Occupancy Adjustment
€500
Maximum Group Size
8

Meet Your Facilitator(s)

Jennifer Young

Jennifer Young is a personal stylist, speaker, and founder of Emerge by Jennifer, with more than 15 years of experience helping people use style as a powerful expression of identity, confidence, and personal growth. Drawing on a diverse career spanning the stage, corporate leadership, human-centered design, and fashion, she created the signature Style by Design™ Framework to help clients align their story, style, and presence. For this retreat, Jennifer brings her thoughtful and deeply personal approach to Tuscany, guiding guests through an exploration of creativity, craftsmanship, and self-expression while creating space to reconnect with who they are and who they are becoming.

Rich, Meaningful, Memorable Travel Awaits

Life Beyond the Room (LBR) is a sensorial™ travel concierge dedicated to creating custom, unique itineraries for travelers seeking authentic experiences immersed in the lifestyle, flavors, and culture of each region. Our local managers live in the destination countries and speak the local languages, allowing us to create incredible partnerships so our travelers can step off the beaten path, beyond the hotel room, and discover places unknown to most tourists.

Our commitment to sustainability ensures that your impact is positive. You will have the trip of a lifetime while making a long-lasting positive impact on the places you visit and the people you encounter. You will meet as a guest and leave as a friend! If you have questions about this group trip or are interested in custom travel design, don’t hesitate to contact us!