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Isola Bella, Taormina, Sicily

Capri, Sorrento & Sicily

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27 May 2016 by Chris Kyprianou

Coastal Italy has long held a firm grip on my imagination as a holiday destination. I was all too ready to tuck into gourmet pizzas on a seaside esplanade, wander through ruins left by ancient civilisations and simply take some time out on an exclusive beach. And, I’m happy to report that expectations were well and truly met. On ferry jaunts and private transfers in convertibles I explored islands both intimate and historic in Capri and Sicily, as well as discovering the picturesque delights of the World Heritage Amalfi Coast.


Famous Capri has hosted everyone from the ancient world’s cultural elite to Hollywood superstars. While I didn’t stay in a classical Greek villa, I did get to experience a touch of film star luxury in the superb Hotel Capri Palace where five star terraced rooms look out over the island’s azure waters. And, its setting in hilltop Anacapri is equally charming. A 20 minutes’ taxi ride from central Capri Town, it’s an authentic village home to an abundance of restaurants and intimate bars.

It was also an excellent springboard for exploring the island. A particular favourite was the Gardens of Augustus, an early 20th century collection of botanical gardens on the island’s central south coast. Designed to showcase the island’s flora – think pretty geraniums and delicate dahlias – they look out over Capri in its entirety. From its hilltop perch you can enjoy views of Mt. Solaro and round over to the Bay of Marina Piccola and the faraglioni, Capri’s famous rock formations that puncture its coastal waters in standalone jags. I also visited the Certosa di San Giacomo Monastery. Founded in 1363, its grand Renaissance design manifests itself in Roman marble columns and richly detailed cloisters.

Picture of Capri in the sunshine
I highly recommend Capri to anybody who likes sun, great food and beautiful beaches


Elevated Sorrento is a historic resort town whose colourful jumble of craft shops and restaurants tumbles down towards its picturesque cliffs and beach sliver. I stayed in Hotel La Favorita, tucked away among lush Mediterranean gardens just a few minutes from that famed cliff edge. Highlights included indulgent breakfasts and a rooftop pool that looked over the Bay of Naples. And, as the western gateway to the Amalfi Coast, it seemed only appropriate to explore further.

On a full day private tour I was whisked along country lanes and coast hugging routes being treated to breathtaking views of the Mediterranean Sea at every turn. It’s no surprise that this UNESCO-listed slice of paradise has become something of a second home to many of the world’s rich and famous. Along the way we stopped off in pretty towns and villages including Positano, an idyllic collection of pastel coloured residences, boutiques and cafés that fall down impossibly steep streets and look out over bright blue waters.

Picture of Positano at dusk in Sorrento, Sicily
At dusk, Positano looked absolutely stunning set against the waters below


This crown jewel of Mediterranean culture, Sicily is the picturesque meeting point of Byzantine artistry, a rich classical history and a collection of Baroque architectural gems. And, with a volcanic landscape informed by Mt. Etna’s famous outbursts, its mountains, islets and sparkling waters make for idyllic swims, dives and hikes. My Sicilian home was Taormina, a town first founded in the 4th century BC before being reinvigorated by the 18 th century Grand Tours. Today, its ancient Greek amphitheatres, medieval churches and gulf views out to Mt. Etna are just as beautiful as when they entertained the likes of Homer and, slightly more recently, DH Lawrence. I even managed to stay right in among the history in a converted 14 th century monastery, complete with bright grounds and spacious wings.

Image of a backstreet in Taormina, Sicily
Taormina had a lovely, quaint feel to it – a lot more laid-back than Palermo

From Taormina, I made use of a group tour to explore Sicily’s highlights. We started with the Valley of the Temples (known locally as Valle dei Templi) in Agrigento, what is the island’s most impressive archaeological site. Here, you’ll find evidence of an entire ruined city, spanning 1,300 hectares, featuring majestic edifices and ridge-top temples dedicated to Greek gods. We then made our way to Piazza Armenia; set in the Sicilian hinterlands at 721m above sea level, it’s home to the famed Villa Romana del Casale. Once a 4th century Roman hunting lodge, today it’s home to some of the best-preserved examples of Roman mosaics.

Beautiful photo of the Valley of Temples in Agrigento, Sicily
The Valley of Temples is one of the most impressive Roman ruins I've ever seen!

What was your highlight?

Everyone has an image of coastal Italy – dramatic cliffs, charming villages and delicious seafood – so I have to say my highlight was the destinations living up to my own lofty expectations.

What would be your trip for this holiday?

Stay patient. On the islands, traffic can get busy especially over July and August. My best recommendation would be to make the most of quieter shoulder seasons.

Why should a client travel there?

Italy is one of those destinations that has a bit of everything – rich history, world-beating gastronomy, honeymoon romance and plenty of Mediterranean sunshine to relax in.

What is unique about the destination?

Each seaside village and every compact town has its own characterful charm; there’s plenty to explore to keep you coming back year on year.

Journey Experience

Fantastic apart from one delay due to freak thunderstorms!

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8-day tailor-made self-drive from £995 pp incl. flights

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Sicily's rich past has given rise to a uniquely contrasting history and it's a similar story when it comes to its food and wine. You’ll take it all in with stays in boutique properties and pretty country drives, with the island’s famous gastronomy showcased in wine tastings and open-kitchen dining.

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