The Ultimate Greek Island Hopping Itinerary: 7 Days At Sea

Greek island hopping itinerary 7 days
Photo by Joseph Richard Francis
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Welcome to our ultimate Greek island hopping itinerary, 7 days of jumping from spot to spot on the map of the Aegean Sea. Here, we’ve formulated what we think is the perfect week-long trip through the region. It includes some of Greece’s must-see islands and a few more off-the-beaten-path spots for those secret coves and more chilled village experiences alike.

The majority of the trip takes place in the Cyclades chain. That’s because it’s home to arguably the most iconic islands of the lot, from party-mad Mykonos to stunning Santorini. We also chose the area because it’s pretty easy to navigate on ferries and yacht charters, so you shouldn’t find getting from A-to-B too hard even if you don’t have your own boat.

You can also make this Greek island hopping itinerary 7 days or longer. That all depends on how much time you have. It’s a versatile plan of action, which you could complete pretty quick, moving from island to island each day, or take longer over if you’re looking for a bit more Mediterranean sun and sea.

Day 1 – Athens to Mykonos

Mykonos
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Leg one of our ultimate Greek island hopping itinerary 7 days whisks you away from the bustle of Athens. You’ll need to get down to the port in Piraeus to escape the metropolis. There are regular ferries from there to Mykonos that take about 2.5 hours in all (go for the faster flying dolphin options if you can).

The trip there should be rather pretty. You’ll pass straight down the side of the Saronic Gulf, with rugged Hydra Island on one side and the outline of the ancient temples of Cape Sounio on the other. Then the boat bends eastwards and heads straight past the island of Ermoupoli to Mykonos itself.

We’d say try to arrive as early as you can. There’s nothing quite like a breakfast in the idyllic area of Mykonos Town’s old port. If possible, score a seat in the al fresco terrace outside of BouBoulo. They do some of the top breakfasts on the island – think stacks of sweet pancakes covered in local fruit and juices made from Mykonos oranges!

For the afternoon, make a trip by bus to see the iconic beaches of south-west Mykonos. You’ve got a few choices, ranging from jet-setter Psarrou to the snorkeling haven of Paraga Beach. However, we’d recommend going straight for Super Paradise Beach. It really sums up the vibes here; all good, easy-going. There’s a legendary beach bar (the Super Paradise Beach Club) right on the sand there, too, and the shindigs start pretty early.

At night, return to Mykonos Town to watch the sunset from the Venetian windmills (a rite of passage on Mykonos). Afterwards, there are guaranteed parties in raucous Scandinavian Bar or the chic LGBTQ+ venues of Little Venice.

Day 2 – Mykonos to Naxos

Naxos
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There’s at least one daily high-speed ferry on the popular route from Mykonos to Naxos during the main summer season. They won’t take any more than an hour before dropping you off in the bustling port town of Chora, the capital of the island and one of the main transport hubs for the whole Cyclades chain.

Don’t linger too long there. A string of fantastic beaches rolls out just the south. Plaka Beach is one of the best of all and it’s only a short drive from where the ferries come in. Expect a two-mile strand of golden powder with lightly lapping seas that are great for families with the kids in tow.

Couples or adventurers might want to push on some more down the coastline to the more isolated coves of Alyko Beach (also sometimes spelled Aliko). That area is set under a scented cedar forest and even offers sections for nudists if you really want to get a-tanning.

If there’s any time left in the day and you can rent an ATV, it’s also worth venturing into the mountains of Naxos. They are some of the highest in the Cyclades. They host pine woods and olive farms, along with the haunting remains of the Temple of Demeter (dating from 530 BC) and even the cave where the great god Zeus was said to have been raised as a child.

When evening closes in, be sure to beeline back to the port. It’s crowned by the ruins of an ancient shrine to Apollo. That’s fronted by a large stone gateway that is one of the top spots to watch the sunset on the island.

Day 3 – Naxos to Ios

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It won’t be hard to seek out a ferry connection between these two islands. Naxos is the main transport hub of the region, so there’s likely to be lots of options between June and August (though we would recommend pre-booking your tickets, as links to all islands – especially ones that draw hefty crowds like Ios – can sell fast for the high season).

Get there as early as you can, because Ios has way more up its sleeve than its hedonistic reputation might imply…

We love the backcountry. It’s a crumpled mass of scrub-covered peaks that hits a zenith on Mount Pyrgos. You can hike there if you’re feeling energetic, to see the amazing monastery of Agios Ioannis and get a 360-degree panorama around this part of the Aegean Sea. Alternatively, you could stick to the coast. Ios actually boasts some of the finest sands around, with beaches like Mylopotas and Kalamos leading the way.

Of course, the number one reason that Ios features in this Greek island hopping itinerary 7 days is because of its nightlife. It’s the party mecca of the whole country, offering sleepless ouzo bars and dance clubs that go on until sunup. That’s all centered on Ios Chora, the main town. Try not to give yourself too much of a hangover, though, because you’ll be up early traveling…

Day 4 – Ios to Folegandros

Folegandros
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What awaits next is one of the lesser-known Cyclades: Folegandros. Here, the pace of your Greek island hopping itinerary 7 days will slow and you’ll be able to experience a more untouched part of the Aegean Sea.

Your first port of call should be Chora. It’s the main town on Folengandros and is hailed as one of the most stunning in all of Greece. Just look how it perches precipitously on the black-rock cliffs, looking like a wisp of cloud above the glimmering waters below. To be honest, half of the joy of this barren and rocky isle is simply in getting lost between the cubist cottages there, people watching on the plazas, and dining on long Greek lunches in the main square.

There’s one thing you have to do, though. Cue the Church of Panagia. Sat at the end of a zigzagging path that begins on the north side of Chora, it’s where virtually everyone on the island goes when sunset approaches. Make the climb and you’ll be rewarded with views of the light dying over the rugged western half of the island. It’s pretty epic.

Day 5 – Folegandros to Milos

Milos
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Milos sits just a little west over the strait from Folegandros. It’s a much larger island but only about half of it is inhabited. The other half is all rugged hills and dusty quarries, ringed by high cliffs that drop dramatically into the Aegean in a medley of caves and grottoes and amphitheatre-like bays.

In fact, the coastline of Milos is certainly its biggest draw. Take some time to plan a day’s outing by boat there. That’s really the only way to appreciate the sheer diversity of what’s in store…

You should venture north first, to see the white-rock inlets of Sarakiniko Beach and the crumpled rock headlands of the Papafragas Caves. After that, set the compass to the southern coast of the island. That’s altogether wilder and less built up. Tsigrado Beach is a must, especially for snorkelers who appreciate uber-clear water. We also love the area around Kleftiko further west. It includes glimpses of strange rock arches and rock stacks.

At night, the best place to be in Milos is the village of Trypiti. There, white-painted tavernas are watched over by the old citadel of Plaka Castle. If you have time, there are also archaic Christian catacombs to explore in the vicinity.

Day 6 – Milos to Santorini

Santorini
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A classic leg on a classic Cyclades island hopping trip, Milos to Santorini goes through the heart of the region. The aim? One of the most iconic Greek islands of all. Believe it or not, the whole place was once a colossal mega volcano. But that exploded with dramatic force back in ancient times, leaving a collapsed caldera that’s half sunken into the sea. No wonder Santorini is famed around the planet for its views, eh?

Be sure to grab yourself somewhere to stay on the caldera side of the island. The villages of Akrotiri, Imerovigli, and Oia (the best in our opinion) are all great for that. For something livelier, you could also aim for the island’s capital of Fira.

The main thing to do on Santorini is to take in the view. With just a single night on the island during this Greek island hopping itinerary 7 days, that means you should make a beeline straight for one of the high-perched bars or tavernas – Tropical Bar (in Fira) and Feredini (in Oia) are two top picks.

If you have time before the sunset approaches, then it’s also worth exploring the bathing spots of Ammoudi Bay just below Oia on the north coast. They’re naturally warmed by underground springs and have some fantastic little snorkeling coves.

Day 7 – Santorini to Crete – the perfect end to a Greek island hopping itinerary 7 days

Photo by Joseph Richard Francis

The final hop on our Greek island hopping itinerary 7 days is the longest of the lot. It leaves behind the Cyclades and whizzes you the whole breadth of the Cretan Sea to Greece’s largest island, Crete itself. It’s the perfect place to complete your jaunt because you can spend weeks and weeks here and not get bored, so feel free to elongate your stay in the home of tzatziki and feta as long as you like.

For us, Chania is the prime arrival point. It’s a charming Venetian city with big fortresses that date back to the 15th century and an old lighthouse keeping watch on the bay. It’s also the perfect base for exploring the Gramvousa Peninsula, which is capped off by the jaw-dropping beach of Balos, a dream-like swirl of white sand and sky-blue sea that could easily fit into the Caribbean.

If you’ve got the time, we’d also recommend an adventure through the Lefka Ori (the wild mountain range in the heart of Crete) to the southern shore. It’s got ex-hippy enclaves like Matala where people used to live in the coastal caves and stunning beaches like Glyka Nera, all backed by goat-filled gorges that are a haven for hikers and nature lovers (Samaria is one of the best but Aradena is perhaps the more impressive).

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Joe has been a freelance travel writer for over nine years. His writing and roaming have taken him from the colonial towns of Mexico to the chowks of Mumbai to the Southern Alps of New Zealand. When he's not putting together the next epic blog on the best Greek islands or ski fields in France, you can usually find him surfing or hiking – his two top hobbies.