7 nights from £1,890 per person
Based on two people sharing, with seven nights in carefully selected accommodation and private transfers arranged for the main holiday route.
Final pricing depends on your travel dates, room choice and availability.
Enjoy Taormina’s ancient theatre, gardens and evening restaurants before travelling south to Siracusa. Four nights there leave time for Ortigia, archaeology and breakfast by the water at Giuggiulena. We arrange the private transfers for the main journey.
Based on two people sharing, with seven nights in carefully selected accommodation and private transfers arranged for the main holiday route.
Final pricing depends on your travel dates, room choice and availability.
A week brings together Taormina’s hillside views and Siracusa’s life beside the sea. Walk through historic streets, enjoy local food and choose an excursion with a private guide if you would like to explore further.
A good fit for travellers who value history, sea views, characterful hotels and independent time, but prefer the main logistics to be arranged for them.
Spend three nights enjoying Taormina’s town and views, followed by four in Siracusa for Ortigia, ancient sites and time on the seafront terraces.
We arrange private transfers for the main journey. Explore each town on foot, use taxis when useful and add guided outings to Etna or the south-east according to your interests.
Taormina brings gardens, terraces and theatrical coastal scenery. Siracusa follows with Greek heritage, Ortigia and a more lived-in seafront atmosphere.
Enjoy Villa Carlotta’s terraces and rooftop dining in Taormina, then settle into Giuggiulena’s small seafront house in Siracusa. Both invite you to spend time at the hotel as well as exploring.
Walk into Taormina from Villa Carlotta for the ancient theatre, gardens and restaurants. Return for drinks or dinner on the rooftop, looking over the sea, and enjoy the hotel’s quieter setting between outings.
Sabrina and Claudia welcome you to Giuggiulena, a small house directly above the Ionian Sea. Enjoy Sicilian breakfast by the water, spend time on the terraces and head into Ortigia for its lanes and restaurants. Steps lead to the rocky shore; swimming depends on sea conditions.
These practical guides provide useful background for the two main destinations, alongside ideas for Mount Etna and specialist private touring.
Discover Taormina’s Greek theatre, panoramic terraces, historic centre and coastal setting, with practical ideas for making the most of a three-night stay.
Discover guide → SiracusaExplore Siracusa’s ancient sites, Ortigia’s layered history, sea-facing streets and the places that reward a slower few days in the city.
Discover guide → Mount EtnaA practical introduction to visiting Mount Etna, including its contrasting landscapes and the different ways an excursion can be arranged from Taormina.
Discover guide → Private touringSee how private touring can add context to the journey through geology, landscape, food and local culture, with the experience shaped around your interests.
Discover guide →This seven-night journey keeps eastern Sicily deliberately simple. These longer self-drive itineraries offer more independence, additional stays and a broader view of the island.
A more extensive island journey for travellers who want to connect the landscapes around Taormina and Siracusa with wine country, archaeological sites and Palermo.
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A slower exploration of the east for travellers who want more time around Mount Etna, Noto, Siracusa and the coast, with a car providing greater freedom between the main bases.
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A western route with a different character: Palermo’s cultural energy, the vineyards and open landscapes around Menfi, followed by a relaxed coastal finish in San Vito Lo Capo.
View this holiday →The journey follows a simple route through eastern Sicily, beginning amid Taormina’s hillside scenery before continuing south to Siracusa and the historic island of Ortigia.
Private transfers are arranged for the principal journey, so there is no need to collect a hire car or manage parking in either destination.
We can adapt the dates, rooms and experiences to suit you. Enquire early for the best choice at these small hotels, especially if you would like a particular sea-view room or a popular spring or autumn week.
Tell us what you have in mindAdd nights in either town, choose another hotel or include time near Mount Etna or Noto. We can arrange the connections and suggest how to make the most of the extra days.
Tell us your preferred travel dates, likely budget, room requirements and the balance you want between culture, food, scenery, private touring and independent time.
ExpertoItaly will discuss your ideas and prepare a personal itinerary with hotels, transfers and your chosen experiences, together with a clear land-only price. Flights are booked separately.
Share as much or as little as you know at this stage. The important details can be refined together once we understand the kind of journey you are considering.