Sicily often begins with a few names on a wish list: Taormina, Palermo, Mount Etna, perhaps a few days by the sea. The next question is how to bring them together.
When we discuss a Sicily itinerary with a travel advisor, I like to start with the time available and the kind of journey the guests imagine.
Our team looks at arrival and departure airports, accommodation and how often the guests want to change hotels. Those first decisions help shape a journey with time for both the places and the people traveling.
A week exploring one area feels very different from two weeks moving across the island.
Eastern Sicily
Eastern Sicily: Taormina, Mount Etna and Ortigia
An Eastern Sicily itinerary brings together Catania, Taormina, Mount Etna and Siracusa, including its historic island center, Ortigia.
The appeal is the variety: city streets and markets, an ancient theater overlooking the coast, volcanic landscapes and archaeological sites. These places form the core of the eastern route described by Sicily’s official tourism board.
For a first trip to Sicily with around five to seven nights, we would consider a selection of these places, reviewing a split between the Taormina area and Ortigia.
A couple might prefer a sea-view hotel and evenings in town. A family may want fewer excursions and somewhere comfortable to spend the afternoon. We choose the bases around those preferences, then plan the days.
The Baroque southeast
Southeastern Sicily: Ortigia and the Baroque towns
For guests drawn to architecture, food and smaller historic centers, we can focus on Ortigia, Noto, Ragusa Ibla, Modica and Scicli.
This can be an extension of an Eastern Sicily itinerary or the focus of a separate stay. A boutique hotel in town offers a different experience from a countryside villa with space for everyone to gather.
Our background in property management helps us assess those choices: bedroom layouts, bathrooms, shared spaces and access. A beautiful property becomes the right choice when it works for the people staying there.
Val di Noto
Noto, Ragusa, Modica and Scicli belong to the UNESCO-listed Late Baroque Towns of the Val di Noto. Ortigia adds a coastal setting to a journey through the southeast.
Western Sicily
Palermo and Western Sicily: culture, food and the coast
A Western Sicily itinerary can begin with Palermo and Monreale, then continue toward Segesta, Trapani, Erice and Marsala.
Palermo brings historic monuments, markets and food traditions into the journey. Farther west, the possibilities include archaeological visits, hilltop streets, salt pans and wineries. Cefalù, east of Palermo on the northern coast, can also be considered as an excursion or a separate stay.
For around six to eight nights, our team would explore a combination of Palermo and a second base in the west, selecting the outings according to interests.
I like the possibility of giving the stay two different settings: time in the city followed by a coastal hotel or a private villa. It creates room for exploration and for enjoying the accommodation itself.
Across the island
From Palermo to Taormina: a wider Sicily itinerary
For guests who want to explore both sides, we can consider a journey between Palermo and Catania, traveling in either direction. One possible route, following stops that appear in established cross-island itineraries:
- Palermo
Historic monuments, markets and food traditions - Valley of the Temples, Agrigento
The archaeological highlight of the southern coast - Villa Romana del Casale
Near Piazza Armerina, a possible stop on the inland journey - Southeastern Sicily and Siracusa
The Baroque towns and the historic island center of Ortigia - Taormina
The ancient theater above the coast, with Mount Etna close by
I would generally begin discussing this option with ten to fourteen nights available, adjusting the stops to the preferred pace.
Arriving at one airport and leaving from another may reduce backtracking. Our team checks the flights before recommending the direction, then considers where a guided visit or lunch can fit naturally into a transfer day.
Map
The places in this guide
From Taormina in the east to Trapani in the west, the main places mentioned in this guide.
- Taormina. Ancient theater, sea views and easy access to Mount Etna.
- Mount Etna. Volcanic landscapes on the eastern side of the island.
- Ortigia, Siracusa. The historic island center of Siracusa.
- Noto, Ragusa Ibla, Modica and Scicli. The UNESCO-listed Late Baroque towns of the Val di Noto.
- Agrigento. The Valley of the Temples, on the cross-island route.
- Palermo and Monreale. Historic monuments, markets and food traditions.
- Trapani, Erice and Marsala. Hilltop streets, salt pans and wineries in the west.
The islands
Adding the Aeolian or Egadi Islands
An island stay deserves its own place in the schedule.
The Aeolian Islands
Off Sicily’s northern coast, the archipelago includes Lipari, Salina, Panarea and Stromboli. Milazzo is one of the ports used to reach the islands.
The Egadi Islands
Favignana, Levanzo and Marettimo lie off western Sicily and can be considered alongside a stay around Trapani.
For a journey centered on the sea, an island may become the main destination. For others, a few additional nights can introduce a different rhythm.
We review the season, sea connections, luggage and onward travel before proposing the combination. The arrival and departure arrangements matter just as much as the stay.
Planning
How many days should you spend in Sicily?
These are the starting points I would use when choosing a Sicily itinerary:
| Time available | How we would approach the journey |
|---|---|
| Four or five nights | Focus on one area, with a limited number of outings |
| Six to eight nights | Explore eastern or western Sicily, choosing a few bases and excursions |
| Ten to fourteen nights | Consider a wider route connecting several areas |
| Additional nights | Include an island stay, more coastal time or a slower villa holiday |
For families and groups, we also consider how much time everyone wants together. A private chef dinner at the villa or an afternoon by the pool may belong in the plan as much as another guided visit.
Good to know
A seven-day Sicily itinerary should still leave time to enjoy the places where the guests sleep. A longer journey offers more possibilities, but it does not need a different hotel every night.
Beyond Sicily
Combining Sicily with mainland Italy
Sicily can come before or after Rome, the Amalfi Coast or Puglia, depending on the connections available for the travel dates.
We check flights first, then work through the airport transfers and accommodation. For the Amalfi Coast, that includes the journey to or from Naples Airport. For Puglia, we review which airport and flight options suit the route.
Working with our local partners, our team coordinates property access, meeting points, luggage, guides and daily timings. During the journey, our concierge team remains a point of contact for the advisor and the guests.
Our approach
Bringing the journey together
What interests me most is understanding what brings someone to Sicily: family roots, a love of history, food, time by the sea or simply the wish to discover somewhere new.
Those conversations help us choose the route. From there, our team brings together accommodation, private Sicily tours, transfers and local experiences, working alongside the travel advisor.
The aim is a journey that feels personal: enough planning to make the days comfortable, and enough time for a place, a conversation or a shared meal to become a lasting memory.
For travel advisors
Plan a Sicily itinerary with us
Travel advisors are welcome to contact My Exclusive Italy to discuss Sicily itineraries, from focused regional stays to wider journeys across the island and combinations with mainland Italy.
Want us to plan your trip to Sicily or elsewhere in Italy?
