The Ultimate 10 Day Greek Island Hopping Itinerary

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The phrase ‘island-hopping’ was most probably invented for the Greek islands. With more than 200 islands, from the big-name drawcards like Santorini and Mykonos to the obscure-yet-idyllic hideaway spots like Milos, the Greek island hopping itinerary has always been a popular choice among visitors.

Having said that, although the romantic notion of “just hopping on the next boat to anywhere” is very much possible, it definitely pays to do a little advanced planning when visiting Greece. This is especially true in the summer, since hotels and ferries can get booked up.

When planning your trip, keep in the back of your mind that you want to strike a balance between the lively islands and the more secluded ones. The final recommendation in this guide is a true hidden gem that gives everything and more. This 10-day itinerary is all you need to experience the very best of the Greek Islands.

There are countless ways to tweak your itinerary. For example, you can add the lovely island of Milos (on which we have a full itinerary, accommodation guide and restaurant recommendations) onto the beginning of this route. You can also draw inspiration from our comprehensive itinerary for one week in Greece.

When to go Greek Island Hopping

For its almost-guaranteed sunshine, the months of June, July and August are naturally the peak season to visit the Greek islands. Summer trips are more expensive and the ferries, flights and restaurants will be crowded, but it is popular for a reason.

I would recommend September and early October as great months for your Greek island hopping itinerary. The water will have been basking in the sun all summer, making it warm and much more suitable for swimming than in the spring shoulder season.

If you decide to visit in the winter, expect many restaurants and accommodation options to be closed. However, you can get great deals on those which remain open. Ferries and flights can also be disrupted in stormy weather.

Visits to bigger islands like Crete and Rhodes will still be enjoyable in winter. Their historic old towns remain lively all year, and you can still get beautiful sunny (but chilly) weather in winter.

Days 1-2: Paros

Start your Greek island hopping itinerary with the beautiful island of Paros. Famed for its long stretches of sandy coastline, beach bars, and a picturesque old town, Paros is an archetypal Greek island in so many ways.

Beautiful views greet you at every corner of this island. Blue-and-white domed churches dominate the skyline of Paros’s gorgeous villages, and its beaches and watersports are second to none. For this reason, Paros is one of the more popular islands in Greece, and it is a great first stop on your Greek island hopping itinerary.

There are fairly regular flights from Athens, or alternatively you can arrive by ferry from Piraeus or Rafina, both near Athens.

Day 1: Parikia and Krios Beach

Parikia Old Town

After your ferry or flight, check into your hotel near the main town of Parikia – Apollon Boutique Hotel is an excellent option. Get lost in the bougainvillea-lined whitewashed streets as you browse the stylish shops and visit the old town’s cafes for a freddo espresso. Make sure you stop by the Holy Shrine of the Virgin Mary Ekatontapyliani, a significant Orthodox church on the island.

Dionysos Garden Restaurant is a great spot to grab lunch, with fresh seafood being their specialty. Don’t forget to ask if they have any traditional Greek desserts on the menu.

Krios Beach

For the afternoon, take a gentle walk round the bay to Krios Beach, where you’ll find pristine clear waters and beach bars. It’s worth getting a beach lounger here if you can so you can laze away the rest of the day.

Day 2: Naoussa and east coast beaches

Naoussa

Hire a car for the day and head out to explore the north and east coast of Paros. You can sometimes rely on buses to get around the island, although giving yourself flexibility with your own car is always preferable.

The pretty small town of Naoussa sits in the middle of a sheltered bay at the north end of Paros. A quieter and even friendlier version of Parikia, I personally believe that this is one of the most beautiful spots in all of the Cycladic islands. You won’t be able to miss the Venetian Castle, whose walls form the edge of the village marina.

Best beaches on Paros

For the rest of the day, it’s beach time. As you make your way down the east coast, stop by Tsoukalia Beach, Molos Beach and, saving the best for last, Chrissi Akti Beach. Paros is renowned for its windsurfing, but you will also understand why Paros is so famous for its beaches alone.

Days 3-5: Naxos

It’s only a short hop over to Naxos, the undisputed master of the Cycladic islands. I already mentioned that I think Naxos is the ultimate package in terms of Greek destination. With its unrivaled selection of history, nature, beaches and hiking, it really must feature on any properly planned Greek island hopping itinerary.

Since you’ll be here for three days and it’s the largest of the Cycladic islands, it’s worth hiring a car here as well (don’t worry, the next two islands won’t need a rental car quite as much). Since you probably stayed in Parikia on Paros, take this chance to leave the town and stay by the beach. I recommend staying at Villa Kastraki Luxury Apartments)

Day 3: Naxos west coast beaches

Gazing back over towards Paros, spend your day swimming in the cerulean waters of Plaka Beach or Glyfada Beach. The uninterrupted stretches of powdery sand would fit perfectly in the Caribbean, although the crystal-clear water is characteristically Greek.

For a more secluded feel, head down to so-called Hawaii Beach, just a short distance further south.

If you can tear yourself away from the sea, take a short detour inland to visit the Temple of Demeter, and the Bazeos Tower.

Day 4: Naxos Old Town

You will have passed through the ferry port in Naxos Old Town, but today is the day you’ll dive into its age-old charm and vibrant atmosphere.

Naxos can’t be visited without a short walk up to the symbolic Temple of Apollo watching over the bay. If you fancy a dip in the sea, there are nice swimming spots on either side of the peninsula.

The Old Town’s pedestrianized alleyways invite you for the afternoon to get utterly lost. Explore the restaurants, shops and bars nestled in this captivating town. Joining a tour to guide you round the Old Town would be a great idea.

Day 5: Inland Naxos

The center of the island rises to an impressive altitude for a Greek island. Even if you don’t summit Mount Zeus and visit the cave where Dionysus was supposedly raised, there are plenty of interesting mountain villages to explore.

There is, in fact, a fairly well-established circuit that you can follow to take in the most picturesque Naxan villages. Halki, Kaloxylos, Filoti and Apiranthos are all beautiful. There are countless churches, gentle walking paths and panoramic viewpoints scattered across the interior of the island. You can really take your time, explore the villages’ food scene, and make this a whole-day excursion.

Days 6-8: Amorgos

The key rule with finding off-the-beaten-track Greek islands is this: if it doesn’t have an airport, go there. Then take one look at Amorgos, and you’ll see why it doesn’t have an airport.

The result of Amorgos’s dramatic mountain topography is its totally unspoiled identity that it has managed to preserve, alongside fantastic rugged scenery and hiking trails, of course. I thoroughly love Amorgos for exactly these reasons, and would highly encourage anyone on a Greek island hopping itinerary to visit.

Day 6: Katapola and Chora

Katapola: the best place to stay on Amorgos

Your ferry will either pull into Katapola or Aegiali, and I would recommend staying in Katapola, towards the center of the long island. To be honest, the town is fairly quiet, but there are some beautiful short (and flat) walks along the coast out of town.

Amorgos Chora

Late morning, take yourself up the steep hill (it is possible by bus) to the main Chora (old town). The main population centers of many Greek islands are in the central highlands rather than by the coasts, historically to protect themselves against raiders. For the afternoon, explore the Chora of Amorgos’s windmills and the castle rising high above the town.

Day 7: Iconic monasteries and black-pebble beaches

Holy Monastery of the Virgin Mary Chozoviotissa

You’ll pass through the Chora again, but this time the road almost plunges off the south coast of Amorgos to the open sea below. Clinging bravely to the almost-vertical cliff of south Amorgos is the symbol of the island, the Holy Monastery of the Virgin Mary Chozoviotissa. For a small fee, you can enter the monastery and, sometimes, meet monks still living and praying there.

Tours will also take you to the monastery and arrange transport, in case you don’t want to rely on public buses.

South coast beaches

As you can see, the steep cliffs below you don’t allow for the formation of huge sweeping bays like in Paros or Naxos, but the swimming off Amorgos is truly unforgettable. I speak absolutely no word of a lie when I claim that this is probably the clearest water that I have ever swum in.

The black pebble beach at Agia Anna sits just below the monastery, and was made famous by Luc Besson’s movie The Big Blue. Since it is incredibly picturesque and quite small, expect it to be a bit crowded on the shore, but you came here to enjoy the clear water.

Alternatively, my personal favorite swimming spot along the coast is much further west, at Mouros Beach. The black stones, together with diving areas, steep drop-off and unbelievable visibility of what must be more than 30 meters create an absolutely magical experience.

Day 8: Aegiali and circular hiking trails

On your final day on Amorgos, take a trip up to Aegiali, the other sizeable town on Amorgos. On your drive up, pass by Agios Pavlos Beach on the north coast for a quick swim.

After coffee in Aegiali, there are a number of circular walks that you can take. These trails of varying distances and difficulties take you up above the town, past isolated chapels and through small villages.

When you pass through the village of Tholaria, have a late lunch at Taverna Panorama. Meat-eaters will love the tender “goat in the oven” (probably as fresh as physically possible), whereas the vegetarian options such as bean stews, stuffed vegetables and salads are equally as fresh and delicious.

Days 9-10: Astypalaia

Trust me: absolutely anyone who has been to Astypalaia ranks it in their top three Greek islands, at the very least. Dubbed the “butterfly of the Aegean,” the name “Astypalaia” hasn’t spread outside Greece that much. Its relative obscurity and unique beauty are exactly why this island is the true hidden gem of the Greek islands.

From Amorgos, the ferry trip itself feels like pushing out into the unknown. Astypalaia straddles the edge of the Dodecanese and Cycladic island groups, but it’s its detachment from both of these major island chains has left it relatively untouched.

Astypalaia boasts the brownish dramatic landscape of Santorini, the windmills of Mykonos and the beautiful white houses of Naxos. But the best thing is: it has the crowds of none of them.

Day 9: Chora

Without a doubt, stay in the Chora on this island. The town gradually spreads its way up the hill, and as you pass the windmills halfway up, you’ll find the headland crowned with the impressive Castle of Astypalaia. The views from the top are absolutely stunning.

For food, Salis Kafeneio Mezedopoleio is a fantastic choice if you’re down by the coast. Otherwise, if you’d like a restaurant with a view up near the castle, get the seafood at Ducato Di Astypalea.

Day 10: Boat trip

On the very final day of your Greek island hopping itinerary, sign up for a sailboat day cruise out to the islands of Kounoupi and Koutsomiti. Some boat tours also call by the “Red Cliffs” on Astypalaia itself, a great swimming spot where the adventurous can swim between narrow cracks in the rock.

Trips can easily be arranged here or by travel agents near the port.

Ending your Greek Island Hopping Itinerary

You could spend forever island hopping in Greece, but all good things must come to an end.

From Astypalaia, travel back to mainland Greece either by the daily flight to Athens, or take the long ferry ride. Alternatively, it’s not too far further east to Kos, which is very well connected with other European airports.

If you have some time in Athens before your flight home, don’t miss our local’s guide to spending three days in Athens.

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