Custom Sicily vacations, hand crafted by our Italy based specialists.
Plan Your Trip
For curious kids and culture-loving parents, Sicily Together is a 12-day summer itinerary where markets, mosaics, and ancient ruins become the backdrop for laughter, learning, and shared discoveries. The
Explore Rome, Florence, Venice and Sicily as art, history and breathtaking landscapes create the ultimate Italian journey. Starting from $6,404 per person.
Discover Palermo, Taormina and Sicily’s treasures as ancient ruins, seaside villages and breathtaking landscapes create an unforgettable island escape. Starting from $1,268 per person.
Experience Sicily’s wonders as you explore Catania, Siracusa, Palermo and Taormina—where history, flavors and landscapes create an unforgettable island adventure. Starting from $2,309 per person.
A wonderful itinerary to discover Sicily, a land so rich in history, art, different cultures and traditions: it will blow you away.
An enchanting itinerary that takes you from Catania to Palermo in this unique mini escorted tour. Visit some of the most important highlights of Sicily and discover the history
Sicily is a world of its own, a Mediterranean crossroads where Greek temples, Norman cathedrals, baroque towns, and an active volcano all share one island. It rewards travelers who give it room, and it is best experienced as a journey across several bases rather than a single stop. Every Sicily vacation we design is custom built by our Italy based specialists around your interests. Browse the sample itineraries below, then let us shape one entirely around you.
Most Sicily packages sold online are fixed departures on a rigid schedule. We work the opposite way. As a custom tour operator that has designed private Italian vacations for more than twenty years, we begin with a blank page and build your Sicily trip from your priorities out. That means private local guides, access arranged in advance where it matters, and a daily rhythm with room to breathe. You get the depth of a trip planned by insiders with the ease of having every detail handled for you.
Sicily layers three thousand years of history into a single island. The Valley of the Temples at Agrigento rivals anything in Greece, the mosaics of the Villa Romana del Casale astonish, and the baroque towns of the southeast, Noto, Ragusa, and Modica, glow golden in the afternoon light. Taormina perches above the sea with Mount Etna as its backdrop, and the volcano itself can be explored with a guide. Palermo pulses with markets and Arab Norman monuments, while the coastline offers everything from the temples of Segesta to quiet swimming coves. With a private driver, the island opens up at a comfortable pace.
Picture a six or seven day rhythm across two or three bases. Begin in the southeast around Ragusa and Noto for the baroque towns and Villa Romana, move to Taormina for Etna and the coast, and add Agrigento or Palermo depending on your interests. Private drivers connect the legs so the island feels effortless. This is only a sketch, and your itinerary is reshaped until every day feels right.
Sicily shifts its character depending on who is traveling. For couples we lean into its romance and quiet corners, for families we keep younger travelers engaged with hands on experiences and the right pacing, and for multi generational trips and small private groups we balance shared highlights with free time so everyone gets the version of Sicily they came for. The structure of each day is calibrated to the travelers, not the other way around.
Sicilian food is among the most distinctive in Italy, shaped by Arab, Greek, and Spanish influences, from arancini and caponata to cannoli and granita. A street food tour of a Palermo market, a lesson in Sicilian sweets, or a tasting of Etna wines grown on volcanic soil all bring the island’s food culture to life. We build these experiences around genuine local tradition and the season.
Sicily is substantial enough to be a trip in itself, but it pairs well with a few days in Rome or Naples at either end for contrast. Many travelers dedicate a full week to the island and open in a mainland city. When Sicily is one chapter of a longer trip, we design the whole route as a single seamless plan.
Sicily rewards good timing, and the best season depends on the trip you want. Spring and autumn generally bring the most comfortable days and the fullest calendar, summer is warm and lively, and the quieter months trade energy for space. Whenever you travel, the planning follows the same path. We begin with a conversation about what matters most to you, design a first draft itinerary for your review, and refine it together until every day feels right before a single reservation is confirmed.
Six to eight days let you experience the southeast, Taormina and Etna, and either Agrigento or Palermo without rushing. We tailor the route to your interests and pace.
We provide private drivers so you can move between regions comfortably without navigating unfamiliar roads. That leaves you free to enjoy the scenery.
Yes. Guided experiences on Etna, from gentle viewpoints to higher elevation walks and wine tastings on its slopes, are a highlight we build around your comfort.
Spring and autumn are ideal, with warm seas and comfortable days. Summer is hot and lively, winter is mild and quiet, and we plan around whenever you travel.
Very much so, with beaches, active volcanoes, and hands on food experiences. We calibrate the pace and the activities to your group.
Yes. Accommodations, private drivers, guides, and experiences are arranged as one coordinated plan, confirmed before you travel.
When you are ready, our specialists will turn any of the sample itineraries above into a Sicily vacation designed entirely around you. Tell us how you like to travel, who is coming with you, and what you most want to experience, and we will handle the rest from the first draft to the final confirmation. Start planning your custom Sicily vacation today.
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About this guide: This Sicily vacation planning page was written by the Italian born travel specialists at Trips 2 Italy, a custom tour operator that has designed hand crafted Italian vacations for over two decades. The sample itineraries above reflect the same first hand knowledge our team draws on when we build a private Sicily trip around a traveler’s interests, dates, and pace. Use it for your research, then let us translate it into a vacation designed entirely around you.
