One Week Island Hopping in Greece

Last Updated on 23rd January 2024 by Sophie Nadeau

This post may contain affiliate links. Please check out my privacy policy and disclosure for more information.

Ancient Greece, and more specifically many of the islands in the Aegean Sea, is long thought of as to have been the Cradle of Western Civilization. Filled with oodles of isles (most notably the collection which makes up the Cyclades), a glittering ocean and a whole load of history, here’s a quick guide to island hopping in Greece, as well as things to know before you go and essentials you must pack for your Greek Islands adventure!

Travel Tips for Island Hopping in Greece

There are several ways you can go about booking to go island hopping in Greece. While many people opt to go the DIY self-made route, ensuring that they’ll be able to enjoy all of the ‘must-see’ items on their Greece bucket list, others prefer to embark on cruises, which means that all of the small details are taken care of for you, not to mention all food offerings and accommodation options!

You will surely not be disappointed should you opt to visit Greece, though there are a number of things to consider while planning your trip, such as the best time of the year to visit and other travel considerations. Check out our guide to the best of Greece tips for more information and inspiration!

One week island hopping in Greece Itinerary

I’ve just spent a week-long sailing through the Aegean, a place known for its art and culture, and a place where the islands have been inhabited for millennia. Complete with sandy stretches, volcanic geology and all of the stunning islands you could ever ask for, there’s no better place in the world to go island hopping!

Day 1: Set sail from Piraeus

All aboard! Ships towards the Cyclades Islands regularly depart from Piraeus, a port town not far from the Greek capital of Athens. Easy to reach from Athens International Airport, Piraeus (meaning ‘the place over the passage’) was inhabited in Ancient times as Πειραιεύς, Peiraieús and it’s thought that people have lived in the area since for well over four and a half thousand years. 

Day 2: Mykonos

My first true taste of Greece came in the form of Mykonos, a dreamy island best-known for its iconic windmills, striking sunsets, and the capital city of the same name, Mykonos town.

Some of the very best things to do on the island include wandering through the narrow lanes among typically Greek architecture, sampling local Greek cuisine (think lots of sea-inspired menus!), and swimming in the crystal clear water.

Should you opt to visit Mykonos, just bear in mind that as one of the more popular Greek islands, it can get incredibly busy in the middle of the summer! As such, in order to truly enjoy Mykonos, I highly recommend visiting in May or October! For more island inspiration check out this sample one day itinerary for Mykonos.

Day 3: Milos

Milos is one of the lesser-known of the Cyclades Islands. And if it’s not already on your radar, then you definitely need to add this beautiful place to your European bucket list ASAP! For the island, which is also known as ‘Melos’ (or Μήλος in Greek) has been inhabited almost consistently for some 12,000 years.

The Greek island is also allegedly the birthplace of Aphrodite. This legend came about thanks, in part, to the discovery of the Venus de Milo, a statue from antiquity which was rediscovered on the volcanic island during the 19th-century. Today, the marble statue can be found in the Louvre Museum in Paris.

So, if you want to soak up a heady combination of bright sun and ancient history then you should totally head to Milos. After all, there are ancient Catacombs to visit (which were used as burial chambers in Antiquity), as well as Roman ruins to discover. It’s also worth noting that Milos is home to plenty of charming towns and villages!

If you’re feeling a little more adventurous, then consider hiring a boat for a day with some friends and discovering a different side of the island. Check here for some of the best-reviewed boat tours of Milos that you can book in advance.

Days 4 & 5: Santorini

The most famous of all the Greek Islands is Santorini. Characterised by its rocky landscapes, volcanic beaches (of which several are formed of black sand), and beautiful hilltop villages, if you’ve seen a photo of Greece recently, it was likely snapped in Santorini!

Some of the very best things to do on the island include wandering around the village of Oia (i.e. where those blue domes are located), sampling some local cuisine, and enjoying the view at sunset when candy colours dance across the sky and light up the Aegean Sea.

If you’re looking for another perspective on the island, and notably Oia, be sure to head to the village at sunrise for some snaps without the crowds! Otherwise, you should note that Oia is also where you’ll find the iconic blue domes of Santorini.

Day 6: Heraklion, Crete

Crete is one of the more populated islands of the Aegean, while Heraklion is the capital and largest city on Crete. Second only to tourism, olive oil production is one of the biggest industries on the island. In fact, it’s estimated that there are some 35 million olive trees on the island and between 50 and 70 thousand tonnes of olive oil are produced here on an annual basis.

Elsewhere on the island, the Bronze Age Palace of Knossos is one of the most visited cultural sites in Greece. Also known as Cnossos, the place where the palace ruins now lie are thought to have been inhabited as early as 7000 BCE.

The Palace itself dates back to the Minoan period and the main building alone covered an area of up to three acres! And that’s not all! Instead, in Greek mythology, the Palace of Knossos is associated with King Minos and the Minotaur.

The legend tells that the King’s wife, Pasiphae, fell in love with a sacred bull (at that time, the bull was the most sacred of all of the animals) and as a result of a curse from the gods, fell pregnant with the bull’s child.

The resulting infant was half-man, half-bull. I.e. the Minotaur. With the body of a man and the head of a bull, no one was allowed to kill the queen’s son and so Minos had Daedalus construct a massive labyrinth from which the Minotaur wouldn’t be able to escape.

Rumour has it that the Palace of Knossos may well be where the labyrinth was located. Better yet, due to the complexity of the palace, it may well be the palace itself that was the labyrinth…

Day 7: Samos

The hidden gem of the Aegean Sea, here in Samos the waters are some of the clearest that you’ll find anywhere in Europe. While there, some of our group remarked that the tropical nature of the island meant that it seemed like we had been magically transported to the Carribean!

The scenery is lush and the landscape vibrant with flowers and greenery thanks to the sheer number of natural springs found all over the island. Samos is actually best-known as being the birthplce of Pythagoras. The famous mathematician (do you remember his theorem from maths at school? () was born on the island during the 6th-century BC.

Since antiquity, Samos has been famed for its vineyards and grapes have been cultivated on the island for millennia. Today, award-winning sweet wine is still produced on the island which lies just a mile from the coast of Turkey. If you want to learn more about the production of wine on the island (as well as sample some of the stuff for yourself), then head to the Samos Wine Museum (Μουσείο Κρασιού Σάμου).

Best time to go Island Hopping in Greece

The hottest months of the year are July and August when temperatures can soar above forty degrees. This also happens to be ‘high season’ meaning that crowds are at their highest. While in Santorini, our tour guide informed us that some days in Santorini during the summer months, you literally can’t even walk down many of the narrow streets!

As such, in order to make the most of the weather, be sure to visit in May, early June, late September, October or November when everything is still open but you’ll get more of the place to yourself! The days are still fairly long and the weather is perfect for exploring (not too hot, nor too cold!)

How to go Island Hopping in Greece

If you are looking for a more independent way to travel, then it’s certainly possible to plan your full trip from start to finish. Flights and ferry boats are both available from one island to another. However, island hopping in Greece can soon add up to astronomical costs (for example, flights between Santorini and Athens are much more expensive than those between Paris and Santorini!).

During my time island hopping across the Aegean Sea, I spent the entire week onboard a cruise with Celestyal Cruises. While many people (wrongly) believe that cruising isn’t for young people, it totally is! Pros of cruising include waking up in a new destination each morning and (quite literally) travelling with your hotel…

Thank you so much to Celestyal Cruises and Discover Greece for hosting me on the #blogtrottersgr press trip island hopping in Greece. All opinions and photos are my own!