Forget battered backpacks and snail’s-pace ferries – Greek island-hopping has gone upmarket. Gone are the days when island-hopping was the preserve of adventurous backpackers (or wealthy yacht owners); nowadays, comfortable ferries and convenient timetables make travelling between isles as easy as a hop, skip and a jump to the nearest ferry port.
When to go
If you’re after the best beach weather, go for the summer months. But if you’re happy to trade a few degrees of warmth for fewer crowds, May and September are great times to visit. If you’re thinking of April or October, bear in mind that there may be a reduced ferry service in some places.
Which islands to choose
There are thousands of Greek islands, but if you want a little luxury with your island-hopping holiday, here are our favourite combinations…
Mykonos & Santorini
Mykonos and Santorini are possibly Greece’s chicest islands. They’ve got typically Greek good looks – all whitewashed houses trimmed with hot-pink bougainvillea and churches topped with sapphire-blue domes – and more than their fair share of luxe hotels and gourmet restaurants.
In Mykonos, spend your days flitting between the island’s sandy beaches; try Super Paradise for a lively vibe, Aghios Ioannis for a peaceful feel, and Psarou for something between the two. As the sun starts to set, plot a course for Little Venice. This waterside area of Mykonos Town has the best sunset views (and cocktail bars). On Santorini it’s all about the views, with the island’s west-coast towns perching atop dramatic cliffs that overlook a sunken volcanic crater. Save an evening for Oia (the sugar-cube village you’ll have seen on all the postcards) and a day for exploring the volcano by boat.
Santorini’s capital, Fira, is a great stop for a bit of souvenir shopping. The shops and boutiques are situated just back off the cliff edge, so while you’re mooching through the cobbled alleyways and browsing the lace kaftans and delicate filigree jewellery, you’ll catch a glimpse the Aegean every now and then. Sam Grist, Travel Expert
Getting between Mykonos and Santorini
Ferry times between Mykonos and Santorini can vary depending on which type of ferry you opt for, but generally they’ll take around three hours. The Cyclades experience a fair amount of wind in the summer months, making the water choppy. If you’re prone to seasickness, you might want to take a tablet before you leave.
Where to stay
For a boutique island-hopping adventure, opt for De.Light Boutique Hotel in Mykonos and Sun Rocks in Santorini. The former is a member of the Small Luxury Hotels of the World group and has a peaceful pool overlooking Delos Island, while the latter boasts caldera views and 18 beautifully designed rooms and suites.
Mykonos, Santorini & Crete
Why stop at two? Mykonos, Santorini and Crete make a fantastic island-hopping combination. Adding Crete to the mix gives you the chance to explore the grand Minoan palace of Knossos and the mysterious islet of Spinalonga. For a taster of big-town life, spend a few hours strolling the cobbled streets of Rethymnon; if you’d rather take things slow, seek out laid-back villages like Aghios Nikolaos or Plaka.
Getting between Mykonos, Santorini & Crete
See above for details of ferries from Mykonos to Santorini. From Santorini, ferries take about two hours to reach Heraklion, on Crete’s northern coast. From here, we’ll organise a private transfer to take you to your hotel, whichever part of the island you’re staying on.
The ports at all destinations were easy to navigate. You might have to take the timings with a pinch of salt, but I was never left waiting too long. Grab an iced coffee as you soak up the ports’ atmosphere – it definitely beats hours at airports. The ferries themselves aren’t particularly glamourous but they are easy, with designated seat numbers and places to store your luggage. Christina Oliver, Content Editor
Where to stay
Grace Hotels has luxe properties in both Mykonos and Santorini. In Mykonos, you’ll find a serene, all-white hotel with a sea-view pool and a beach two minutes’ walk away. Grace Santorini, meanwhile, offers up an infinity-edge pool and a fantastic Med-fusion restaurant. Once you get to Crete, you’ve got plenty of luxury options – Daios Cove Luxury Resort & Villas (pictured above) and St Nicholas Bay Resort in Aghios Nikolaos and Domes of Elounda, Autograph Collection in Plaka are a few of our favourites.
Rhodes & Kos
The most popular islands in the Dodecanese make a great pairing. Start off in Rhodes. It’s supposedly the sunniest spot in Greece, and has plenty of postcard-worthy beaches to help you make the most of it. Earmark an afternoon to explore Rhodes Town – its old quarter is a medley of medieval, Venetian, Byzantine and Ottoman buildings. For the second leg of your island-hopping holiday, you’ll head north-west to Kos. There’s history to uncover in Kos Town and the ancient archaeological site of Asklepion, but it’s the golden sandy beaches that really shine here.
In Kos, I’d highly recommend a trip to Zia, a beautiful mountain town in the centre of the island with amazing views. While you’re in Rhodes, I’d suggest a visit to whitewashed Lindos and its famous hilltop acropolis. Natasha Starkin, Travel Expert
Getting between Rhodes & Kos
Ferries between Rhodes and Kos run a couple of times a day – the morning ferry is usually the fastest service, taking just under two and a half hours. As with all of our holidays, we’ll arrange a private transfer to take you between the ferry ports and your hotels (as well as to and from the airport).
Where to stay
In Rhodes, you could try the Amathus Elite Suites. The sea-view suites are sleek and contemporary (some come with private pools, too) and you’re only four kilometres from Rhodes Town. For your stay on Kos, take a look at Neptune Resort & Spa – it’s got a beachfront address and a traditional Greek taverna for trying local dishes.
Island-hopping day trips
If you still want to explore but would rather base yourself in one place, there are still lots of options for island-hopping day trips. From Corfu, it’s a short crossing to the picture-perfect villages of Paxos and Antipaxos; from Skiathos, you can head over to unspoilt Skopelos for the day; and from Kefalonia, it’s easy to spend a few hours on neighbouring Ithaca or Zante.