Inspiration for your own tailor-made trip
Italy – Sicily – Palermo – Marsala – Agrigento – Ragusa – Syracuse – Riposto
100% customisable for you
Your holiday begins today with a three-hour flight to Palermo this morning. When you land in Sicily’s exciting capital, you’ll be met at the airport and privately transferred to your hotel, where you’ll spend two nights in the heart of the city – a perfect base for exploring. When you’ve settled in, head up to the rooftop for sweeping views across Palermo and toast to the start of your adventure with a glass (or two) of regional white wine.
On your first full day in Sicily, meet your local guide for a private tour of Palermo. Lace up your comfiest walking shoes and set off to explore the city’s rich history and architecture. Admire highlights like the Abatellis Palace and its gallery of Sicilian art, the Arab-Norman landmarks of the Church of the Holy Spirit and Norman Palace before marvelling at the Baroque beauty of Santa Caterina Church. Wrap up the tour with a visit to the Capuchin Catacombs, an eerie but fascinating underground burial site lined with centuries-old mummified remains.
The rest of the day is yours to spend as you like. Wander the old town’s alleyways and sun-drenched squares or get lost in lively markets. Feeling peckish? Sample Palermitan street food like frittelle (crispy fried batter snacks), panelle (chickpea fritters) and arancina (deep-fried rice balls). And if you fancy yourself an art aficionado, head to the archaeological museum for its splendid collection of Greek and Phoenician masterpieces.
As evening rolls in, ask our Concierge for their favourite local spot for dinner – perfect for sampling Sicilian mezze, with a few scoops of gelato to finish, of course.
This morning, pick up your hire car and drive to Marsala, a journey of just under two hours. Roll the windows down, stick on our destination-specific playlist to set the mood, and enjoy the scenery as you head west.
When you arrive in Marsala, check in to a beautifully restored farmhouse – your home for the next two nights. Drop your bags, then head out to explore.
While this city is famously known for its sweet wine, there’s far more to discover than just cellar doors alone. Once a Carthaginian and later Saracen stronghold, the city holds great significance in Italy’s history: it was here that Giuseppe Garibaldi landed in 1860, paving the way for the country’s unification. Over the next couple of days, take time to wander the seafront and explore the characterful old town, home to the Baroque Chiesa Madre and a number of fascinating archaeological sites.
In the mood for another glass of wine? We can arrange a candlelit dinner and tasting at the Martinez Winery, founded in 1866.
Hit the road again this morning and drive southeast to Agrigento – a journey of around two hours. On the way, pull over in the spa town of Sciacca. Take a dip in the thermal pools, stretch out on its soft sand beaches and grab a bite to eat down by the fishing port. Then wander the old town, from the medieval Castello Vecchio to its network of cathedrals, churches and castles that reflect the town’s historic past.
When you arrive in Agrigento, check in for the night in an 18th-century villa, complete with a panoramic terrace overlooking the valley.
And when you’re ready to head back out, set off on a guided tour of Agrigento’s UNESCO-listed Valley of the Temples. This ancient Greek colony, founded in the sixth century BCE, was one of the Mediterranean’s great cities and its striking Doric temples are testament to its significance and scale.
As the sun begins to set, a walk among the ruins is particularly magical, and your guide will know all the best photo spots for those golden-hour shots.
Your road trip continues south with a drive to the UNESCO-listed town of Ragusa. Break up this two-and-a-half-hour journey with a stop in the hilltop town of Enna, where sweeping views across the Sicilian countryside make for the perfect pause. Visit the Villa Casale in Piazza Armerina to admire its world-famous Roman mosaics. Want to learn more? We can arrange a private guided tour of this extraordinary site.
When you arrive in Ragusa, check into your hotel for the next two nights before heading out to get a feel for the city. Take your time exploring the winding streets of Ragusa Ibla, the atmospheric old town, where elegant churches such as San Giorgio and Santissime Anime del Purgatorio sit among honey-hued stone buildings and sun-drenched piazzas. Cross over into Ragusa Superiore, the newer part of the city, to discover the Cathedral of San Giovanni Battista, along with grand palaces and religious architecture.
Each evening, sit al fresco at a local restaurant and savour dishes made with locally grown produce, or opt for a tasting session in a medieval crypt.
Gear up for another scenic drive this morning of around one hour and a half, heading east along the coast to Syracuse. No Sicilian road trip is complete without a couple of memorable pit stops, and today is no exception. Break up the journey in the towns of Modica and Noto, two stunning jewels of Baroque architecture, both rebuilt after an earthquake in 1693.
When you arrive, head to your hotel on the island of Ortigia, the atmospheric heart of the old town. This evening, indulge in another delicious dinner before heading in for an early night.
After breakfast, head out to meet your private guide for a tour of Syracuse, tailored to your pace and interests. Rich in history, the city is home to some of Sicily’s most impressive Greek and Roman remains and your guide will bring it all to life as you go.
Begin at the Archaeological Park Neapolis, which boasts the largest Greek theatre in Sicily, before continuing on to Ortigia. Connected to the mainland by two bridges, this island feels like an open-air museum where Greek, Norman, Aragonese and Baroque influences are woven into every street and square.
As the day winds down, make your way to the water’s edge, where views stretch out across the bay of Syracuse – the perfect setting for dinner as the sun begins to set. Think fresh pasta, wood-fired pizza and perhaps a generous slice of tiramisu.
Today, drive one hour and 15 minutes to your final destination on this grand tour of Sicily: Riposto.
You’ll spend the next three nights here, surrounded by orange and lemon trees, with time to settle into a slower pace and enjoy the simple things – like long, lazy breakfasts done properly. After checking in, the rest of the day is yours. Wander into town to get your bearings or simply kick back and relax at your hotel.
Over the next two days, it’s all about some serious R&R. Settle into life in Riposto, a laid-back port town on the Ionian coast, where things move at their own pace. An important trading post for wine, citrus fruits and olive oil, it’s also a working fishing town. Boats head out at dawn and return with the day’s catch – think skipjack, conger eel and sea bass – so there’s plenty of local flavour to sample while you’re here.
Stroll into town to visit monuments such as the 19th-century Basilica Matrice San Pietro or wander down to the waterfront for a Sicilian granita (a refreshing semi-frozen dessert) and a bit of people-watching.
If you fancy getting out and about, take a day trip into the charming city of Taormina, or head towards Mount Etna, one of the world’s most active volcanoes.
And for the ultimate Italian experience, we can also arrange a private tour of the Etna vineyards, best explored behind the wheel of a classic Fiat 500.
Sadly, it’s time to say arrivederci to Italy. This morning, hit the road one last time for the one hour drive back to Catania Airport, where you’ll drop off your hire car here before boarding your flight back to the UK. You’ll spend around three hours in the air – plenty of time to start plotting your next adventure…
Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
