There’s something timeless about Italy.
The way the light catches the terracotta rooftops at sunset. The layered aroma of espresso, fresh herbs, and worn cobblestone. The warmth of a welcome that feels more like a homecoming than a check-in.

In Fall 2026, I’ll be bringing a small group of travelers with me to experience all of that and more on a carefully curated journey through Sicily—one of Italy’s most soulful, flavorful, and history-rich regions.

This isn’t a whirlwind tour. It’s a deep dive into the good life, Italian style.

What to Expect

We’ll take our time. There will be wine-paired lunches in quiet countryside vineyards. Sun-soaked boat days along the Ionian coast. A morning market stroll that leads to a hands-on cooking class in a local kitchen. And afternoons free to wander, nap, or do whatever your heart craves.

We’ll explore ancient ruins and bustling piazzas. Hear stories passed down through generations. Share meals around long tables. And soak up the rhythm of Sicilian life—not as tourists, but as welcomed guests.

I’m hand-selecting boutique hotels that embody comfort and authenticity—places where service feels personal and every detail is considered.

Why This Trip? Why Sicily?

Italy has long been a favorite, but Sicily is something else entirely.
It’s layered with influences—Greek, Roman, Arabic, Spanish—and you can taste it in the food, see it in the architecture, and feel it in the traditions. The island tells a thousand stories, and we’ll get to experience them together.

This trip is for the traveler who craves culture, connection, and beauty—without the crowds. It’s for those who want time to savor. It’s also limited to just 10 guests, so every detail can be personalized, and the group dynamic stays intimate and easy.

Want to Come?

Details, pricing, and the full itinerary will be released to my waitlist first before opening to the public. And if my past group trips are any indication… it won’t stay open for long.

No commitment—just first access when booking opens.

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If Italy has been calling your name—or if you’re ready to experience it in a way that’s intentional, delicious, and deeply memorable—I hope you’ll consider joining me.

It’s going to be special. Something to remember.

In kindness,

Travis