From A Seat at the Board Table to a Seat at the Tuscan Table:
My Journey to Creating Women’s Retreats in Tuscany
The Power of Sharing a Meal
From my own dining room to the Tuscan farm table, I’ve seen how sharing a meal dissolves barriers, expands empathy, and transforms strangers into friends.
There is always room for one more chair at our table.
And I would love to save a seat for you.
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Ciao. I’m Janine Pisani O’Rourke, founder of Together in Tuscany, proud Italian-American, certified life coach, and former HR executive. I am also a wife, mother of two “launched” adult children, and the owner of two silly Wheaten Terriers.
With 30 years spent at conference room and board tables, I’ve guided leaders, navigated complexity, and created environments where people felt seen and supported.
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The table that shaped me most wasn’t in a corporate office. It was the long, crowded dining table of my childhood in New York, in a close-knit Italian family. When more guests arrived than we had space for, plywood boards were added and leaves extended so no one was left without a seat. The message was clear: there is always room for you here.
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Though I now live in Virginia, my roots are deeply Italian. Both sets of great-grandparents immigrated from Italy in the late 1800s and early 1900s, and I’ve worked to keep Italian traditions alive in my own home, especially through cooking. I have a deep appreciation for authentic, delicious Italian food, olive oil, and wine, and I bring that same discernment and care to the experiences I design for my guests.
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Have you ever found yourself somewhere and felt a familiar pull, as if you’ve been there before? That’s how I feel every time I’m in Italy. That sense of belonging, safety, and comfort, combined with warm hospitality, incredible food, and amazing wine, led me to choose Tuscany as the home for my retreats. I envisioned creating something truly special: soul-nourishing, small-group women’s retreats in a Tuscan villa. After all, who hasn’t dreamed of staying in a Tuscan villa?
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Our retreats are rooted in shared experiences that spark genuine connection. Over my HR career, I’ve spent decades understanding human behavior, navigating diverse personalities, and creating spaces where people feel seen, supported, and connected. Today, I use that same expertise, to design small-group retreats that intentionally foster community and help women rediscover themselves.
We invite you to join us on one of our small-group retreats and experience the magic of Tuscany for yourself.
You Belong Here
Our retreats are for women who love to slow down and savor the rhythm of Italian life. They’re curious, open-hearted, and drawn to beauty, culture, and meaningful conversation. They may be recently retired and wondering what’s next, an empty nester rediscovering their own rhythm, traveling solo for the first time in years, or craving meaningful connection, not just another tour.
They come for the food, wine, and magic of Italy, and often leave with deeper connection, fresh inspiration, and a new circle of friends.
Why Choose Us
Small Groups, Big Connections
Traveling in intimate groups of 8–14 guests means more flexibility, more laughter, and more genuine connection with your travel companions and the locals you’ll meet along the way.
Stress-Free From Start to Finish
From train station pickup to scheduled excursions, we handle every detail so you can simply show up and enjoy. No planning, no guesswork, just pure enjoyment.
Authentic Local Living
Stay in hand-picked villas and farmhouses nestled in the heart of Tuscany. These aren’t hotels. They’re homes filled with history, beauty, and the comforts you deserve.
Travel That Feels Like Family
You’ll be warmly welcomed by our extended Tuscan family, our chefs, drivers, guides, and friends who make you feel right at home.
A Taste of the Real Tuscany
Enjoy farm-to-table meals, private chef dinners, wine tastings at family-run vineyards, and hands-on cooking classes with local experts. Every flavor tells a story.
Come See For Yourself
