EXPERIENCE SICILY

an insider’s trip into the heart of southern italy

From dramatic cliffside towns to volcanic vineyards, a founder’s journey through Sicily is a Mediterranean escape like no other — every day is filled with beauty.

WHY VISIT SICILY WITH US?

tailored itineraries for a truly personal escape

We invite you to experience the authentic culture of Sicily, one full of kindness and warmth. Home to some of the world’s most enchanting beaches and timeless villages, this iconic Italian island draws travelers from across the globe. Sicilian people will welcome you with open arms, especially when you’re traveling alongside locals like us. Our friends will open their private homes and family-owned vineyards, revealing a side of Sicily few travelers ever see. Every detail of your journey will be customized to reflect your pace, preferences, and passions.

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WHAT WONDERS AWAIT YOU?

These are two examples of our customizable journeys that reveal the best of Sicily:

SPRING ITALIAN RETREAT BY THE COAST

Embark on a 10-day journey through sicily and taormina
See spring unfold and discover the heart of Sicily.

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SPARKLING SEAS & SEASONAL HARVESTS

Bespoke 10-day escape in sicily and taormina
Revel in Sicilian autumn, one of our favorite times to visit.

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A GLIMPSE INTO SICILY

every season brings its own treasures

Found in the heart of the Mediterranean, Sicily is one of our favorite destinations in all of Italy. From its cerulean waters and sunlit beaches to towering volcanoes and cliffside towns, the island feels both ancient and modern. We recommend visiting in the spring or fall, when crowds are smaller and harvests are abundant — citrus groves bursting in the spring and grapes and olives at their peak in the fall. We’ll design a journey for you that balances unforgettable meals, relaxing beach days, and encounters with Sicily’s most storied landscapes.

OUR TRAVEL PHILOSOPHY

TAORMINA

This elegant hillside town is our home base in Sicily. With its sandy beaches, historical architecture, and proximity to Mt. Etna, the tallest active volcano in Europe, it’s no surprise that Taormina is a seaside destination among celebrities and locals alike.

VISIT IN THE SPRING OR THE FALL

CATANIA

Further south from Taormina, sits the bustling port city of Catania. With local museums and fish markets, it’s a beautiful area to explore and sightsee. The city is also very close to Mt. Etna, with hiking trails all the way up to the summit.

VISIT IN THE SPRING OR THE FALL

PALERMO

As the capital of Sicily, Palermo is full of city attractions and experiences. It’s located northwest on the island and sits along the Tyrrhenian Sea. Palermo is an easy day trip from Taormina. While there, soak in local art, ancient royal tombs, historic markets, and Sicilian cuisine.

VISIT IN THE SPRING OR THE FALL

OUR RECOMMENDED EXPERIENCES

step away from everyday. rediscover connection.

Here are some examples of experiences we could plan for you while visiting Sicily. Let’s curate a founder’s trip that’s uniquely you.

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EXPERIENCE THE FALL GRAPE HARVEST

In the hills of Mt. Etna, we’ll visit a family-owned winery and join generations of family members as they pick the year’s grape harvest, all while enjoying last year’s wine.

RELAX BY THE IONIAN SEA IN TAORMINA

Take a dip in crystal-clear waters and relax under an umbrella with a cocktail in hand. There are many beaches in Taormina to enjoy, including the pebbled Isola Bella or sandy Mazzarò.

SAVOR APERITIVO & A FIVE-COURSE MEAL

From curated boards of meats and cheeses to fish ceviche and homemade pasta, we’ll treat you to some of the best cuisine from award-winning restaurants in Taormina and beyond.

EXPLORE NEARBY TOWNS BY PRIVATE SAILBOAT

Glide along Sicily’s cascading coastline aboard a private sailboat. We’ll plan leisurely day trips to hidden coves, sunset dinner sails, or extended journeys down to Siracusa and Ortigia.

WATCH THE SUNSET WITH A GLASS OF WINE

Sometimes, it’s the simple luxuries that make your trip memorable, like watching the sunset on a private terrace or boat with a crisp glass of white wine from a local winery in hand.

THE FINEST STAYS IN SICILY

luxury accommodations

You’ll be pampered throughout your Sicilian escape. We partner with exceptional hotels, like the San Domenico Palace, a Four Seasons property where White Lotus was filmed, to offer our guests the very best amenities and services.

CHRISTOPHER DEAN, FOUNDER

“In Sicily, you and yours will be treated like family.”

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