SICILIA · 31.05 - 12.06 · 2026

Some trips are vacations. This one is a chapter.

Twelve days across two of the most mythical landscapes in the Mediterranean. Volcanic, ancient, and impossibly beautiful. The kind of place that has been conquered by everyone and absorbed by no one.

Somewhere in between there will be long tables that go late into the night. There will be moments of pure silence and moments of pure chaos. There will be a sunset that stops everyone mid-sentence. There will be something that happens that none of us planned and all of us will remember.

That's the thing about building a trip like this with people like these. The itinerary is just the beginning. The magic is co-created.

Welcome to Sicily. Welcome to la dolce vita.

Let's go!

Our Crew

SANDRA
Keeping us organized without making it feel organized

NICO
Making croissants disappear from the table

ERIN
Drinking and sharing tea in ceremony

CASEY
Keeping it calm during stressful travel

ANAND
Going with the flow

KATIE
Offering travel reiki

KAROLINA
Surrendering to the trip as it comes

KATIE
Bringing curiosity, let’s do it!

KEVIN
Embracing the anxious “Travel Ken”

CHRISTINE
Taking care of tired travel bodies

DAVE
“Mission Impossible Dave”

KYLE
Make everyone love fishing

BRITTANY
Making it to a flight, just in time

ANDRE
Easily adjusting to a new country

Our Accommodation

Villa Sabe
May 31 - June 7

Villa La Segreta
June 7 - June 11

The Journey

Destination Deep Dives