Italy

Legendary Sicily

Trip Dates

October 10 – 20, 2026

Details

A timeless island of stories and flavors

Where ancient myths meet Mediterranean beauty, Sicily is an island unlike any other, with history as layered as its landscapes and flavors as rich as its traditions. From vibrant markets in Palermo to the sunlit vineyards on the slopes of Mount Etna, Sicily is a feast for the senses and a journey into the heart of Italian heritage.

On this 11-day adventure, we’ll wander medieval hilltop towns, explore UNESCO treasures, and savor meals crafted by celebrated chefs and local families alike. With private guides, exclusive culinary experiences, and handpicked luxury accommodations, every detail is carefully crafted to strike a balance between indulgence and discovery. We have curated a truly immersive exploration of Sicily’s soul as told through its cuisine, culture, and landscapes.

Savor Sicily’s legendary flavors

From vibrant street food in Palermo to refined chef-hosted dinners in Siracusa, Sicily offers a culinary tapestry like no other. Indulge in cannoli with a master pastry chef, taste centuries-old Modica chocolate, and sip wines born of volcanic soils on the slopes of Mount Etna.

Step into living history

Walk among ancient temples in Agrigento, explore the cobbled streets of Ortigia and Noto’s baroque grandeur, and stand in awe at Taormina’s 3rd-century BC Greek Theater. Every corner of the island reveals a chapter of its storied past, blending mythology, architecture, and tradition.

Bask in natural splendor

From glittering coastlines and sapphire waters to the dramatic landscapes of Mt. Etna, Sicily’s beauty is undoubtedly breathtaking. Scenic drives and private excursions immerse you in an island where sea, sun, and volcanic earth shape both the land and the flavors on your plate.

Savor Sicily’s culinary traditions, from family-hosted feasts to exclusive winery lunches, set against the backdrop of ancient ruins and sweeping coastal views.

At Delectable Destinations, our carefully crafted itineraries are designed to celebrate the richness of place through food, culture, and connection. In Sicily, that means stepping beyond the ordinary, into bustling markets, private kitchens, and hidden gardens where the island’s heartbeat comes alive.

This exclusive cultural and culinary journey invites you to indulge in activities ranging from winery tours and cooking classes to immersive market walks, historic explorations, and intimate dining experiences. You’ll taste everything from Palermo’s famed street food to Michelin-level cuisine, sip wines from iconic estates and boutique producers, and experience moments of hospitality that feel less like a visit and more like coming home.

By the time we say arrivederci, you’ll not only have savored Sicily but lived it through stories, flavors, and views that linger long after the journey ends.

Delivering your dream trip

Sicily

"Traveling with you, Carol (Delectable Destinations) has spoiled me for traveling any other way!"
Tarah N.
New York, NY
"Carol and her team were the best! Their planning made every day varied, fun, interesting, informative, and perfectly paced."
Diane B.
Greenwich, CT

Included

Not Included

Airfare, insurance, incidentals, personal expenses and anything else not otherwise indicated as included.

Detailed Itinerary:

We’re happy to provide a detailed daily itinerary upon request.
Please contact us at carol@delectabledestinations.com

We would love to go over all the exciting details with you!

CUSTOM TRIPS

Looking for a personalized experience?

Get ready to explore on your own schedule. Don’t miss out on your dream adventure if you can’t find a trip that fits your dates. Embrace flexibility with our Custom Expeditions – tailor your journey and explore the world on your terms. Your unforgettable escape awaits.