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
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Arrivals
The group finds its way in. Bags are dropped, introductions made, the villa becomes home.
What to bring: Nothing but yourself and good energy.
What to wear: Travel comfortable.
Vibe: First hello energy. Soft landing.
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The Gang's All Here!
We ease into the experience with no major plans for day one, allowing the day to unfold naturally as we recharge from travelling and the jet lag.The last arrivals land and the group is finally complete. Fourteen people around one table at Zash restaurant for the first time this trip. This is where it begins.
What to bring: Your appetite and your stories.
What to wear: Smart casual. First impressions and all that.
Vibe: Electric. The moment the trip becomes real.
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Fire and Ferment
An early rise today. We climb an active volcano in the morning and drink wine from its soil in the afternoon. Sicily in one sentence.
What to bring: Medium-long socks (for hiking boots), long hiking trousers, t-shirt and sweatshirt, windbreaker (optional), light scarf, hat, sunglasses, sunscreen, backpack, water bottle. Note: the tour will provide trekking shoes, poles, helmets, wind jackets.
What to wear: Athletic / layers for the mountain, relaxed / flowy for the winery.
Vibe: High effort, high reward. One of those days.
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Golden Drift
A slow morning after a long night... Pool, espresso, bossa nova and sunlight. Sicily at half speed.
By late afternoon, Taormina. Ancient stone, sea air, golden light slipping through narrow streets. Pizza, wine, and the kind of evening that rarely ends when planned.
What to bring: Comfortable walking shoes, light layer for the evening.
What to wear: Relaxed and effortless. Swimwear by day, understated summer elegance by night.
Vibe: Chill and connection.
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Baroque Heat
An early start to a big day. Ancient theatres, market noise, sun on stone. A day that moves through centuries without ever slowing down.
Syracuse first, then Ortigia — salty air, crowded market stalls, a delicious lunch that dissolves into afternoon wandering. By evening, Noto glows gold. One final stroll, one beautiful dinner, and the quiet drive home through the Sicilian dark.
What to bring: Comfortable walking shoes, sunglasses, hat, sunscreen, water bottle, light layer for the evening.
What to wear: Breathable, lightweight, made for movement. Comfortable enough for a full day on foot, polished enough for many photo shoots and dinner in Noto.
Vibe: Big day energy. Sun-drenched, walk-heavy, endlessly rewarding.
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Velvet Afternoon
No alarms today. Just drifting between sun and shade, water and wine, and conversation as the villa slowly wakes around us.
Then Catania — faded grandeur, busy streets, little shops, cold gelato melting too fast in the heat. An aperitivo somewhere beautiful before dinner at Menage, where the evening sharpens slightly at the edges.
What to bring: Comfortable walking shoes, sunglasses, light layer for the evening.
What to wear: Relaxed by day, elevated by night. Something light and effortless that can lean a little more refined for dinner.
Vibe: Unhurried but full. Soft daytime energy, polished evening finish.
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Choose Your Altitude
A day without too many plans. Sea or pool, movement or stillness, high or low, shade or sun. The luxury today is choice.
Some will disappear toward the coast. Others won’t leave the villa at all. And for a few, Sicily unfolds from above — coastline, cliffs, and Etna seen from the quiet of a helicopter headset.
What to bring: The obvious for whatever plans you make.
What to wear: Anything easy and sun-ready. Beachwear by day, relaxed summer dinner attire by night.
Vibe: Free-form. Follow your energy.
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Crossing Over
Suitcases by the door. One last coffee, a few early goodbyes, then we head toward the sea.
Salt air and open water as we cross over to Salina. A new rhythm, a new villa, volcanic silhouettes at sunset. Linen pressed, skin sun-warmed, fancy dinner at Signum as the island slips quietly into evening
What to bring: All your shit, neatly packed up and ready to go.
What to wear: Easy and travel-ready by day, refined island energy by night.
Vibe: A shift in tempo. Soft departures, beautiful arrivals.
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Black Fire, Blue Water
A full day at sea, in style. Salt on skin, wind in our hair, nowhere to be except exactly where we are.
Panarea, with its whitewashed streets, a long lunch and slow wander beneath the sun. Then onward to Stromboli, waiting for nightfall and with hopes to witness fire on the horizon.
What to bring: Swimsuit, sunscreen, sunglasses, towel, light layer for the evening on the boat, non-slip sandals.
What to wear: Swimwear and easy resort pieces.
Vibe: Cinematic. Sun-drunk and unforgettable.
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Island Tempo
No fixed route today. Just scooters, sun, and the freedom to follow whatever road feels right.
Hidden beaches, long lunches, maybe some elevated wine at Capofaro as the afternoon slips by. Then, we make our way to Vulcano for dinner at Il Cappero — arriving in style by sea, dressed for the evening.
What to bring: Swimsuit, sunscreen, sunglasses, comfortable sandals, light layer for the boat ride home.
What to wear: Easy island attire by day, refined summer elegance for elevated dinner.
Vibe: Loose plans, beautiful detours. Sicilian summer at its best.
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Last Light at Sea
One more day on the turquoise water. Sailing slowly around Lipari, chasing hidden coves, swim stops, and whatever catches our eye along the way.
A stroll through town, lunch by the sea, a sun-drenched afternoon that blurs together in the best way. Then back to Salina for an easy dinner in Santa Maria — simple, warm, and exactly right.
What to bring: Swimsuit, sunscreen, sunglasses, towel, comfortable sandals.
What to wear: Swimwear and relaxed resort pieces by day, casual coastal dinner attire by night.
Vibe: Sun-faded and content. The kind of day you’ll miss before it’s even over.
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The Last Evening
Bags packed yet again as we depart from Salina. The islands grow smaller behind us. Salt still on our skin, suitcases a little heavier than when we arrived.
One final afternoon in Catania for wandering, gelato, and perhaps a final piece of Italian linen squeezed into a suitcase. Then a long final dinner together before Sicily slips quietly into memory.
What to bring: Everything
What to wear: Comfortable and travel-ready by day, effortlessly polished for the final dinner.
Vibe: Bittersweet in the most beautiful way.
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Until Next Time
Suitcases zipped, sunglasses tucked away, perhaps one final espresso before the airport.
Then everyone disappears back into their own lives, carrying a little Sicilian sunlight home with them.