For visitors to Southern Europe, planning the perfect itinerary for the Greek islands often tops their list. Its popularity among European holidaymakers is unquestionable year after year. Whether it’s the amazing cuisine, the friendly locals, or the gorgeous islands, visitors keep returning to this island paradise.

The answer is yes to all of these questions, but for a first-time visitor, it can be hard to know where to begin. Here’s an itinerary showcasing the most iconic destinations in Greece to help you plan your Greek island hopping.

How To Get Around The Greek Islands

While some people choose private jet charter flights and others try luxury yachts, you get the best experience of island hopping in Greece by taking the public ferry system. The ferries that depart from Athens are very frequent, efficient, and, most importantly, affordable. The entire experience is unique, making it a must-do attraction before you’ve even done anything.

There are also small high-speed ferries available getting you from island to island at a much faster rate than the big ferries, but for something a little more relaxed larger vessels such as the Blue Star are very similar to cruise ships, offering customers the choice of bars, restaurants, and places to sleep. These ferries are your best option on the windier days when the seas can be choppy.

The Greek island Itinerary

If you have never visited the Greek islands before, the places closest to the top of your bucket list are likely to be Mykonos and Santorini, displaying some of the most beautiful landscapes in all of Greece. Cyclades are great places to make your first ferry voyage and can be easily combined with 2-3 days in Athens for your first island hopping experience. 

In our Greek Island itinerary, we are going to show you a 2-3 day trip starting in Athens, traveling by sea on ferries and boats. Our trip visits Paros – Mykonos – Naxos – Santorini – Milos – Sifnos – Athens. Let us begin.

The Greek island ItineraryParos

Paros is, in many ways, the perfect Greek island – it has something for everyone – and many consider the Cyclades to be the heart of Greek islands. From Athens, it is often the first port of call after arriving from the Cyclades, so it’s a great place to start your adventure.

Paros can be found in the middle of the Aegean Sea, known in ancient times for its beautiful white marble. Fast-forward to the modern day and the island is one of the most renowned tourist locations in Greece, with easy transport from Athens by ferry in around three hours or by flight in around 30 minutes. Two of the nicest locations to stay on the island are the fishing port Naoussa and the port town Parikia.


Known for its role in Greek mythology and history, the island of Mykonos is a popular place for leisurely beach days and other outdoor activities, as well as visiting landmarks like the Church of Paraportiani and Delos, another sacred island nearby. You can do some serious celebrity spotting at some of the high-end beach clubs and bars on this party island!


A truly rich history and stunning natural beauty characterize Naxos, the largest island of the Cyclades. On this large island, you can explore many beautiful beaches, many of which are protected and calm, making it a popular family destination. Moreover, it is well-known for its cuisine, particularly for its potato dishes.


Possibly the jewel in the crown of the Cyclades islands, Santorini Island is one of the most magical places in the Aegean Sea. If you’re looking for a romantic getaway, you’ll love watching the sunset in Oia Santorini, which offers stunning views of the caldera. No matter the time of year, Santorini can be crowded due to its immense popularity. This incredible amount of tourists is extended when the cruise ships are in and towards the end of the day at sunset — a must-visit destination and possibly the most beautiful place in all of the Greek islands.


Milos is a great option to be included in your Greek Island itinerary. A volcanic island filled with colorful landscapes and over 40 stunning white sandy beaches. You will be in awe of the unique lunar landscapes found at the Sarakaniko white beaches, home to the Smyrna, the island’s most charming fishing hut. These fishing huts can be rented via Airbnb, giving you an entirely unique experience of where you stay. The food is delicious, and the locals are very accommodating but get there while you can. This island is growing in popularity — and for good reason.


For a final destination, Sifnos delivers relaxing, tranquil, and delicate dovecotes, whitewashed villages, and wondrous views. Famous as a culinary destination, this island has managed to retain its authenticity while still accommodating the tourist market. The people who visit Sifnos tend to return. The port town of Kamares and the small village of Vathi are both great destinations to stay.

As your island hopping vacation draws to a close, it is time to return to Athens, and the great thing is that this is simple. You can take a relaxing 6-hour ferry ride from Sifnos or sail 30 minutes to Milos and catch a short flight. No option of traveling these islands is a bad one.


The Greek islands are waiting to be discovered, with lots of ferries, boats, and flights available, making your trip as fast-paced or relaxing as you desire. If you aren’t looking to fit so many islands into your trip, other options, such as Kefalonia, offer enough attractions and beauty to last an entire holiday.

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