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A beginner’s guide to luxury Greek island hopping in 2023

If you’re completely new to the concept of Greek island hopping and are unsure where to begin, then these are the groups of islands to have on your radar – and each promises a beautiful and memorable experience you’ll be talking about for years to come.

By LLM Reporters   |  

Planning an island-hopping adventure in 2023? The spectacular and diverse isles of Greece offer the chance to immerse yourself in ancient history, wander quaint cobbled streets, take in traditional white-washed architecture and languish on stunning sandy beaches all in one trip – so whatever you’re looking for, you’re certain to find it here. And, with an abundance of warm, sunny weather to enjoy throughout the high season, with temperatures often topping 30 degrees celsius in July and August, it’s the ultimate short-haul destination to visit this summer.

If you’re flying into the Greek capital, as most arrivals do, then catamaran hire in Athens couldn’t be simpler, and is a great place from which to begin exploring. Nevertheless, the Greek islands are well-connected when it comes to domestic flights, so if you have a particular group of islands in mind for your luxury break, then you might also consider jetting into one of the larger islands and setting off from there – which is why it’s good to have an idea of your route ahead of time and plan well in advance.

If you’re completely new to the concept of Greek island hopping and are unsure where to begin, then these are the groups of islands to have on your radar – and each promises a beautiful and memorable experience you’ll be talking about for years to come.

The Cyclades Islands

Aerial view of the famous Portara Gate at Naxos island, Cyclades,
Home to some of the most breath-taking Greek islands of all, and all in relatively close proximity to one another, it’s easy to see why the Cyclades holds such great appeal for island hoppers

Home to some of the most breath-taking Greek islands of all, and all in relatively close proximity to one another, it’s easy to see why the Cyclades holds such great appeal for island hoppers. Your journey is best begun from Piraeus, where you can head straight for chic and sophisticated Mykonos – an island known for its beautiful white-washed architecture, iconic hillside windmills and, of course, its upmarket party atmosphere.

A preferred playground of the rich and famous, its quaint cobbled streets, which are adorned with colourful flowers, are the perfect place to get some show-stopping Instagram shots or to pause for a coffee at one of the many trendy cafés.

Once your thirst for Mykonos has been satisfied, there are plenty more islands to visit within the Cyclades – including breath-taking Santorini, which is a must for enjoying some of the most spectacular sunsets you’ll ever see and is similarly photogenic. If you prefer to avoid the crowds, then make Milos your next stop instead – it’s akin to Santorini in many ways, but is quieter and more unspoilt. Naxos, the largest of the Cyclades, is also worth a visit if you have time – and once you’re done, you can finish your adventure where you started it, back in Piraeus.

The Dodecanese Islands

Symi harbour, with colorful neoclassical mansions covering the slopes near the main city
If you’re eager to explore some of the historical sights the Greek islands have to offer, then head to the Dodecanese, where influences from the ancient Romans and Byzantine and Ottoman rulers of times gone by are in great evidence. Image credit: Cnejevici Ioan Florin/Bigstock.com

If you’re eager to explore some of the historical sights the Greek islands have to offer, then head to the Dodecanese, where influences from the ancient Romans and Byzantine and Ottoman rulers of times gone by are in great evidence. The best spots to take in historic walled cities and castle ruins, the Dodecanese also offer much in the way of great beaches and mouth-watering cuisine – start off in Rhodes, where you can soak up some rays and immerse yourself in the vibrant town atmosphere before setting off on your sailing adventure.

The charming hilltop villages of Karpathos and the lush green forests of Nisyros are both essential stops along the way, while Kalymnos, with its intriguing underwater wrecks and rocky coastline, is an outdoor enthusiast’s dream. To end on a relaxing note, finish off in Kos, which promises pretty beaches, quaint towns and easy access via domestic flight back to Athens.

The Ionian Islands

Beautiful landscape with Holy Monastery of Panagia Vlacherna of the coast Ionian Sea in the Corfu or Kerkyra is a Greek island, Europe
If you’re seeking slightly more comfortable summer temperatures without compromising on beautiful sights and a luxurious experience, then the Ionian islands have got you covered

If you’re seeking slightly more comfortable summer temperatures without compromising on beautiful sights and a luxurious experience, then the Ionian islands have got you covered. Island hopping here is best begun from Corfu, which, with its charming Venetian architecture, is well worth taking some time out to enjoy before you set sail. You can fly in directly from Athens, but be aware that Corfu is one of the most popular holiday islands during high season.

When you’re ready to leave, the nearby island of Paxi is an obvious stop and although tiny, has much to offer, with its rolling green hills, verdant olive groves and historic fishing villages. Next, it’s on to Lefkada, where you can pause to enjoy the many hidden coves and golden, sandy beaches, before moving onwards to Kefalonia for some much-needed R and R to end a busy trip.