THE EXPERIENCE
There are places you visit—and then there are places that stay with you. This journey through Umbria and Tuscany invites you to slow down, savor each moment, and experience Italy in a way that feels both immersive and deeply personal.
From vineyard dinners under the Tuscan sky to hands-on culinary experiences and hidden village exploration, every moment is intentionally designed to help you live fully, connect deeply, and savor every experience.
RETREAT HIGHLIGHTS
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4-course vineyard dinner and wine tasting in Tuscany—an intimate evening set among the vines, blending breathtaking scenery with exceptional cuisine and wines
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Hands-on olive oil experience with local producers
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Curated winery visits and tastings in both Umbria and Tuscany
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Private, authentic Italian cooking experience with a local chef
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Exploration of charming hilltop towns and hidden villages
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Meaningful connection with a small group of like-minded women
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Luxury, private transport (Including transfers from Rome airport and to Florence airport)
Plus so much more—all thoughtfully curated with attention to every detail.
A GLIMPSE OF YOUR EXPERIENCE
Each day is thoughtfully curated to balance experience, connection, and time to simply enjoy Italy.
There are places that you visit—and then there are places that stay with you. This journey through Umbria and Tuscany is designed to be more than a trip. It is an invitation to slow down, to savor, and to experience Italy in a way that feels both meaningful and unforgettable. Surrounded by beauty, rich culture, and shared moments, you’ll find yourself not just exploring a destination—but fully living it.
Day 1 – Arrival & First Impressions Arrive and settle into your surroundings, then ease into the rhythm of Italy with a peaceful, guided mini bus tour of the town—an effortless way to take in its beauty and charm. Enjoy time to explore at your own pace, wandering and discovering as you go. In the evening, we’ll gather for our first dinner together, followed by a traditional passeggiata—a simple, meaningful way to end your first day in Italy.
Day 2 – Taste & Explore Assisi Begin your day with a meaningful visit to one of Assisi’s most renowned and historic sites, where beauty and history come together in a powerful way. From there, step into the warmth of an authentic Italian kitchen for a hands-on culinary experience. Later, enjoy a unique tasting set within a truly memorable setting, thoughtfully enhanced through personal connections. As evening falls, wander the timeless streets of Assisi—taking in the atmosphere, the beauty, and the simple joy of being fully present.
Day 3 – Hidden Gems of Umbria Spend the day exploring the enchanting towns and villages of Umbria—each offering its own unique character, breathtaking views, and authentic Italian charm.
Day 4 – Journey to Tuscany Travel through the rolling countryside into Tuscany, with scenic stops and a unique winery tour along the way, taking in the beauty of the Italian landscape.
Day 5 – Vineyard Dinner Experience An unforgettable evening, dining among vineyard rows with exceptional wines, incredible cuisine, and the glow of the Tuscan sunset.
Day 6 – Tuscany to Florence Continue your journey through Tuscany with a hands-on olive oil experience, deepening your appreciation for the flavors and traditions of the region. From there, travel on to Florence—a city that greets you with beauty, history, and an energy all its own.
Day 7 – Art, Culture & Florence Step into the masterpieces of Florence as you experience iconic sites such as the Uffizi Gallery and the statue of David—moments that are as awe-inspiring as they are unforgettable. Enjoy time to wander the streets, shop, dine, and take in the vibrant life of the city, where every corner tells a story.
Day 8 – Artisans & Farewell Experience the artistry of Florence through a hands-on leather workshop, connecting you to a craft that has been passed down through generations. In the evening, we’ll gather for a special farewell dinner—celebrating the memories made, the friendships formed, and a journey that will remain with you long after you return home.
Please Note: We are thoughtfully finalizing each element of this experience to ensure it is truly exceptional. While the overall structure of the itinerary will remain the same, some details may be refined to further enhance your time in Italy.
INVESTMENT
Investment details will be shared soon as we finalize each element of this experience to ensure it is truly exceptional. Join the interest list to be the first to receive full pricing and booking information.
Includes:
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Accommodations
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Curated experiences and excursions
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Select meals and tastings
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Transportation during the retreat
Does Not Include:
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Airfare
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Travel insurance
MEET YOUR HOST
Hi, I’m Jill, co-founder of Living Loveadorish.
Italy has long held a special place in my heart—from the beauty of the countryside to the warmth of the people and the richness of everyday life. Some of my most meaningful memories have been made there, and it’s a place that continues to draw me back time and time again.
This retreat was created out of a desire to share that experience in a deeper, more personal way—bringing together a small group of women to connect, explore, and truly savor each moment. Not rushed, not overplanned, but experienced fully.
Living Loveadorish was created alongside my husband, Eric, as a reflection of our shared belief that life is meant to be lived with intention—through meaningful travel, connection, and experiences that stay with you. While this particular journey is designed for women, Eric will be part of future Loveadorish experiences as we expand into couples retreats.
For me, this is about more than where you go—it’s about how you feel while you’re there, and the memories you carry with you long after you return home.
I would truly love for you to be part of this experience.
READY TO JOIN US IN ITALY?
Spots are intentionally limited to create a meaningful and intimate experience.
Join the interest list to receive full details, pricing, and early access when booking opens.
