june, 11th 2026
A surprise birthday and a Tuscan table full of strangers
The October escape is full — but the story isn't over yet.
Reading time : 5 min
In this blog article, I’m taking you dreaming with me, once again, through the hills, the vineyards, and the generous tables of this beautiful land.
There’s a moment from our last Tuscan Escape that I keep coming back to.
It was somewhere between the second bottle of wine and the dessert nobody had planned for. Someone had turned 70. We knew, but they didn’t know we knew. And what started as a quiet dinner at the castle — a group of people who had met just days before — turned into something I can only describe as a proper celebration.
Toasts, laughter, a few tears, the kind of singing that sounds better outdoors under a Tuscan sky.
I looked around the table and thought: these people didn’t know each other a week ago. That’s what keeps happening on these trips.
And it never stops surprising me.
Our October 2026 Tuscan Escape is fully booked. Every single spot.
In the past few weeks, many of you wrote to me — some a little too late, some just by a matter of days — and I had to say no.
Something I genuinely hate doing.
So Jill and I decided to do something about it.
We’re opening the waiting list for the Tuscan Escape May 2nd–9th, 2027. Eight days, seven nights in Tuscany: Chianti Classico, San Gimignano, Siena, Montalcino, Bolgheri, a cooking class, a butcher tour, a winery or three, dinners at the castle, and yes, probably someone’s birthday.
No commitment yet. Just let me know you’re interested, and you’ll be the first to hear when spots open officially. If something in you is already saying yes… trust that.
Just mail me at claudia@callegari.wine and I’ll add you to the list.
From Tuscany, with gratitude and a raised glass,
Claudia 🍷
Ready to toast?
