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Our Tours

Our unique tours are carefully and thoughtfully crafted to display the authentic side of a place. We want our travelers to take a step outside of their comfort zone to truly understand a place as if they were living there. Our partners are passionate in what they do and extremely proud to share their stories with you. You will leave a Grapestained tour with food/wine stains on your clothes, and the stains of unforgettable memories on your heart.

5-Night Nobile Wines, Organic Vines, and a Val d’Orcia Immersion
Spring - Summer - Autumn

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Discover historic Montepulciano, adventure under the Cortona Sun, and meander through the stunning Val d'Orcia and its hilltop towns in this incredible 5-night experience of Tuscan wine, food, and authenticity

Tuscany Yoga & Wine Retreat with Dana Damara
May 9 - 16, 2026

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Connect with Tuscany on a spiritual level through yoga, the Grapestained way. Between yoga sessions with the incredible Dana Damara, we’ll dive into every sensation this land offers: rolling hills, unforgettable wines, homemade feasts, and even the heavenly smell of a pecorino cheese farm. A soulful week of movement, laughter, and the romance of Tuscany.

Women’s Connection Retreat in Tuscany October 20 - 27, 2026

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A retreat for women who lead and are ready to slow down.

This eight-day retreat in Tuscany is an invitation to step out of urgency and into presence. Set just outside the historic hill town of Montepulciano, this experience is designed for women who carry responsibility, make decisions, and hold space for others, rarely giving themselves permission to truly rest.

5 Night Exclusive Bolgheri and Val d'Orcia
Coming Soon

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Discover Italy's famous Super Tuscan wines on an all exclusive, one of a kind tasting. Explore historic Montepulciano and Montalcino, while finding hidden gem producers in famous wine regions of Tuscany. Relax on the Tuscan coast and meander through the stunning Val d'Orcia and its hilltop towns in this incredible 5-night experience of Tuscan wine, food, and authenticity

7-Night Grand Tour of Tuscany 
Coming Soon
 

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The ultimate Grapestained experience. Journey across different microclimates, towns, and vineyards, learning from the locals like never before on this unforgettable, 7-night gastronomic and culture filled adventure of jaw-dropping Tuscany.

Private Designed Adventures

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We curate private tours out of Florence. Tell us your interests, desires, time period, and how many days. We will build your most memorable experience in Italy!

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