Do you need the right travel companion to take a wine trip to Tuscany?
This week, in the middle of our third Tuscan Escape with Jill, I found an answer I had never seen so clearly. This group has brought something new to the journey: two mother-daughter pairs and a pair of sisters sharing the same trip.
A group like no other
Our American guests this time come from Tennessee, Indiana, Nebraska, North Carolina… but it’s not the map that struck me. For the first time, we have two mother-daughter pairs and a pair of sisters sharing this journey. The kind of trip people call “once in a lifetime.”
A birthday surprise at Castello La Leccia
On our very first evening, one of our guests had quietly let us know that her daughter was about to turn forty. So in the private dining room at Castello La Leccia in Castellina in Chianti, we surprised her: lights off, a candle on her dessert dish, and the whole group singing Happy Birthday in chorus. The look on her face set the tone for the entire week.
Since then I’ve been watching the little things. The two sisters, finishing each other’s sentences with that ease only a lifetime together can create. And the mothers, who cannot hide their pride when talking about their daughters’ careers. A mother’s eyes say more than words ever could.
Do you need a husband or a partner to travel?
And it made me think.
We sometimes wait for the “right” travel companion. A husband, a partner, the perfect moment. But watching these women laugh over a glass of Chianti Classico, I was reminded of a simple truth: you don’t need a specific person by your side to live a beautiful experience. You just need someone you love sharing beautiful things with.
A mother. A daughter. A sister. A friend. The bond is what makes the journey unforgettable, and Tuscany does the rest.
Tuscan Escape, May 2027
This is why I’m happy to tell you that registrations are open for the next Tuscan Escape, May 2027. We already have our first confirmations, and as you know, these trips are designed for small groups only. If you’d like to join us, write to me at claudia@callegari.wine and I’ll send you all the details, with your husband, your wife, or why not, your daughter, your mom, your dad, your sister. Whoever you love.
The vineyards will be waiting for you.
A presto,
Claudia
By Claudia Callegari, DipWSET Level 4 Certified sommelier. I lead private wine tastings at Tuscan villas, visits to small wineries and the Toscana Wine Club.
Reviewed and updated on October 20, 2026.