I've been to Italy many times, but Tuscany is where it got personal.
In 2024, I planned a week-long motorcycle trip through Tuscany, with San Gimignano as our home base and a list of day trips I'd carefully mapped out. Then Brian got his hands on my itinerary. Every morning, whenever there was a choice between a 45-minute route and a 2-hour route, he picked the 2-hour one. Every single time.
I'm so glad he did. Over 1,000 km of winding backroads took us through Orvieto, Volterra, Bolgheri, Montepulciano, Pienza, Montalcino and more. The scenic route led us to hidden gems no guidebook would have sent us to. It was easily my favorite trip to Italy, no contest.
On one of those unplanned detours, Brian took us to a small chapel standing alone in a wheat field between Pienza and San Quirico d'Orcia. We didn't know then that Chapel Vitaleta was placed there as a symbol of God's blessing of bounty. We just knew it was beautiful, so we stopped.
Two years later, we went back and got married there.
It rained, and then the sun poured out. The Italians say sposa bagnata, sposa fortunata, "wet bride, lucky bride," and I'll gladly take both blessings. It was the most magical day of my life. Tuscany gave me the place where our marriage began, and that's why I can't just recommend it. I have to share it.
Why I want to share it with you
Tuscany rewards people who slow down and wander: the golden hills, the stone villages, the long lunches, and the stops you never planned. I learn something new on every trip, and after this last one I have more insider knowledge than ever about experiencing Italy well.
So from May 15-23, 2027, I'm hosting Under the Tuscan Sun: An Italian Escape with Great Circle Travel. It's a small-group journey for just 12 travelers, perfect for friends, couples, and anyone who loves food and wine and wants the real Tuscany without the stress of planning it.
We'll spend a week in a private villa with a pool, with several dinners prepared by a private chef. Between pool days and slow breakfasts, we'll:
Go on a truffle hunt, followed by a long castle lunch
Taste Brunello at the source in Montalcino
Ride e-bikes through sleepy villages
Take a hands-on cooking class in Montepulciano
Wander the hilltop streets of Cortona and San Gimignano
Spend an evening and dinner in Pienza
And yes, we'll pass by Chapel Vitaleta, the little chapel in the wheat field where it all began for me. I can't wait to share that view with you and tell you the story while it's right in front of us.
Great Circle Travel arranges every detail, from private Mercedes Sprinter transportation to carefully chosen experiences, and I'll be with you all week as your hostess. All you have to do is show up and savor it. And we'll leave room for detours, because that's where the magic happens.
Life is either a daring adventure or nothing at all. Come take the scenic route with me. ❤️
