How does a tailor-made Sicily trip work?

Share your dates, group size and interests using the form. One of our Sicily travel experts will get in touch, design a day-by-day itinerary around you, and refine it with you until it is just right.

Is there a cost to get an itinerary?

No. Requesting a tailored itinerary is free and there is no obligation to book.

How far ahead should I plan my Sicily trip?

The earlier the better, especially for peak season, but we can also help with shorter-notice trips. Tell us your dates and we will check what is possible.

Can you include flights, hotels and activities?

Yes. We can arrange stays, transport, guides and experiences, and advise on flights. Tell us what you would like us to handle.

Can I change the itinerary after I receive it?

Of course. Your itinerary is a starting point. We will adjust the pace, places and activities until you are happy.

Sicily Tours & Trips

Dreaming of Sicily? Tell us when you want to travel, who is coming and what you enjoy, and our travel experts will design a tailor-made itinerary for you. Hotels, transport, guides and experiences are all taken care of.

When?Travellers

Why book with TossnTrips

✓ Itineraries designed by Sicily experts
✓ Free quote, no obligation
✓ 24/7 support while you travel

1Tell us your plans

Share your dates, group and interests in a couple of minutes.

2We design it for you

A travel expert builds a day-by-day itinerary around your trip.

3Travel with confidence

Hotels, transport and guides arranged, with support throughout.

Photos from Sicily

A picturesque aerial shot of a coastal town in Sicily, showcasing the marina and historic architecture. — Photo by Allan Feitor

Explore the breathtaking aerial view of Noto's historic architecture in Sicily. A testament to Baroque beauty. — Photo by Dusan Stupar

Discover the vibrant skyline of Palermo, Sicily capturing historic architecture beneath a bright blue sky. — Photo by Elijah Cobb

Swimmers enjoy the water with Cefalù's historic seaside buildings and rocky cliffs in Sicily, Italy. — Photo by Efrem Efre

Stunning aerial shot of Castellammare del Golfo's marina and town in Sicily, Italy. — Photo by Dmitry Romanoff

Stunning aerial view of the harbor and historic town of Castellammare del Golfo, Sicily, Italy. — Photo by Dmitry Romanoff

Aerial shot of a historic piazza in Palermo, Italy with landmarks and urban architecture. — Photo by Efrem Efre

Aerial view of Caltanissetta with dense buildings and hilly backdrop in Sicily. — Photo by Davide Negro

Charming coastal view of Cefalù, Sicily with historic buildings and clear waters. — Photo by İrem Çilingir

Explore the stunning seaside architecture of Cefalù, Sicily, with rocky backdrops and historic charm. — Photo by Efrem Efre

Itineraries Places Travel styles Who it's for By length FAQ Contact experts

Why travel to Sicily?

Sicily offers something for every kind of traveller, from well-known highlights such as Palermo and Taormina to quieter places worth discovering. A tailored itinerary lets you choose the mix that suits you.

Our team plans every detail around your dates, pace and interests, and is available 24/7 while you travel.

Popular Sicily itineraries

Use these as inspiration. Every trip is tailor-made, so we will adjust the route, pace and hotels to suit you.

7 days

Sicily Highlights

A well-paced week covering the best known sights, with time to explore at your own speed.

PalermoTaorminaMount Etna

10 days

Best of Sicily

A fuller journey that adds more places and a few local experiences along the way.

PalermoTaorminaMount EtnaSyracuseAgrigento

5 days

Palermo & Taormina Short Break

A shorter trip focused on Palermo and Taormina, ideal if you have limited time.

PalermoTaormina

12 days

Mount Etna to Syracuse Journey

A longer route linking Mount Etna and Syracuse, with room for off-the-beaten-path stops.

Mount EtnaSyracuseAgrigentoCefalu

Most popular places in Sicily

Palermo

Taormina

Mount Etna

Syracuse

Agrigento

Cefalu

See Sicily your way

Pick what you enjoy and we will build the trip around it.

Sicily trips for every type of group

Sicily itineraries by length

Sicily trip FAQs

Contact our Sicily travel experts

Our team has planned trips to Sicily and knows the places worth your time. Tell us what you have in mind and we will send you a tailored itinerary, free of charge.

✓ Personal itinerary built around you
✓ Free quote, no obligation to book
✓ Support 24/7, before and during your trip

Get your tailored itinerary

Free, no obligation. Tell us a little about your trip and we will design it around you.

Where would you like to go?When are you travelling?

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