How to Spend 2 Weeks Island Hopping in Greece

Martina Rosado
Written by
Last update:

Athens (1 night)

Athens is the capital of Greece with vibrant modern art and architecture that is on display all over the city. You can walk through the National Gardens and walk up to the Panathenaion, the Temple of Athena, where the first Olympic Games were held.

Mykonos (2 nights)

Delos (day trip from Mykonos)

Few places on Earth really embody Greek mythology and legend so vividly. Upon arrival you’ll find yourself on a beautiful Mediterranean island. The city of Delos is where the ancient Olympian gods used to settle during their time on Earth. Although the mythology is quite full of charades, there is a lot of truth underlying the myths.

The Tomb of Amphitrite was one such place, where this goddess used to remain buried. The original temple was destroyed by earthquakes and pillaging over the years, but it’s been rebuilt to be as close to what the ancients saw as possible. The sight of the temple as a UNESCO world heritage site is quite an amazing one. You’ll probably be surprised by how well the ancient Greeks knew about the moon’s impact on tides and tides on the moon’s impact on the Earth.

The next day, head out to the island of Aegina. It’s the largest of the islands around Delos and the birthplace of the philosopher Socrates. The small town of Avli is where you’ll find the home of Socrates. It’s a quiet village that is still quite religious. It’s an excellent setting in which to visit this philosopher.

Paros (3 nights)

While much of the Greek Isles are beautiful, it’s the Cycladic Islands that are the most stunning. They are breathtaking sea caves and monolithic rock formations, the remnants of a prehistoric past. The islands are mostly volcanic in origin, which is why most of them are so monochromatic. The white limestone of the ancient buildings and the white, sandy beaches contrast with the blue of the Aegean Sea, making it an amazing view everywhere you turn.

The largest of these islands is Naxos, but they are all smaller and more intimate. Whether you choose to pack all your belongings into a backpack and hit each one separately or it’s easier to hop on a flight to Paros (as we did), you’ll quickly fall in love with the serene beauty each island has to offer.

Paros is a popular destination for those seeking a quieter, less developed island. There are tons of places to eat, on almost every street in Paros town, but there are still only about 2,000 people living there. Because of the dry climate, they have a lot of dry olives and also leather. It’s a beautiful town with a long, clean beach to play in as well as a small village atmosphere.

Phoros has the best beaches on the island, all backed by scenic mountain views.

Antiparos (day trip from Paros)

Note: There is a ferry from Paros to Antiparos (Kamari island) that runs about 3 times a day.

You can wake up early on a Saturday morning and catch the 6:45 am ferry to Kamari, and then catch a connecting ferry straight to Paros. The ferry is shared with cars, motorcycles, & bicycles.

You cannot take your car, but there are plenty of taxis in Antiparos, or you can rent a water scooter to get around.

Most people will stay on the island for the night, which makes it a good opportunity to enjoy nightlife.

You could also choose to schedule a daytrip on your own. That way you get more time to experience the island.

Paros (day), Amiras (day trip from Paros), Antiparos (8 day), Delos (day trip from Paros), Leros (fly to Leros and after 2 days on the island, take another ferry to Karpathos island, from there you can take a ferry to occupied Rhodes.

Paros (7 Days)

Amiras (2 days), Paros (2 days).

Kamari (4 days), Kamari (4 days), Leros (1 day),.

Naxos (2 nights)

Greece is not the first place you think of if you’re planning a solo trip, but it really should be. It’s cheap, it’s easy to get around, and no matter where you start, you’ll be able to cover enough ground to see it all. There is a lot to do and see on this trip, but two of the best things to do are visit Naxos and go scuba diving in Santorini.

Agios Kirikos (2 Nights)

Peloponnese and the Gulf of Corinth mean a lot of climbing and hiking. If you are traveling solo, it’s an amazing time to see some of the most beautiful Greece has to offer. The options are endless, and wherever you go you will be able to find amazing natural views.

Santorini (3 Nights)

Santorini is a small volcanic island in the south Aegean sea. The striking nature of this place is amazing, and it’s a pretty chill place, too, with plenty of good food and craft beer. Go scuba diving in this place because it’s amazing.

Santorini (3 nights)

Santorini is a volcanic island located between the Cyclades and the Dodecanese. With a population of 15,170, Santorini is essentially one large town with the requisite beachside cafes, souvenir shops and supermarkets. One look at the island, however, and you’ll know that Santorini is not your typical European tourist destination.

The spectacular scenery of Santorini is a result of the volcanic activity that created this island from a smaller island. The thermal activities of the island have also created different volcanic zones where the earth has dug deep into the earth and the black sand beach is the result. Imagine the whitewashed Cycladic facades and the sun-washed blue sea. It’s as if Greece and the Caribbean had a baby.

Edith Cavell, a British nurse, was executed by the Germans during WWI for helping soldiers escape to the Americans. The British retaliated by severing the hospital that she ran from the rest of the island to prevent German soldiers from finding it. This hospital was deemed a historical landmark and has been restored to original condition. Take a tour to find out more about the place where Cavell hid soldiers.

Milos (2 nights)

Milos, located south of Crete and closer to the island of Naxos, is a stunning island.

It’s quite a contrast to the mountainous weather and style of Santorini. When you climb up from the coastal town of Volax (also known among some as “The rock” or “The volvo”) you’re greeted with a view of rolling hills, pine covered mountains and tan agricultural fields.

The welcome is warm. The people of Milos are all very proud of their heritage and way of life. It’s a spirited culture where the sense of community is very strong. There is a special warmth in the air when you’re there.

Many have described this island as a wonderful escape from the stress of the world. It’s hard not to feel that way, as there are few places in the world that can be described as more beautiful.

The beauty of the island is a draw, but the culture is what makes this island stand out from others. The people are genuine and polite, the food is fresh and delicious, and the views are spectacular.

It’s a natural retreat from life, where time seems to slow down and there is a sense of simplicity.

Athens (1 night)

Athens is the capital of Greece with vibrant modern art and architecture that is on display all over the city. You can walk through the National Gardens and walk up to the Panathenaion, the Temple of Athena, where the first Olympic Games were held.


My first trip to Greece, I flew to Athens and took the only 2 week cruise available on the Black Sea, using Vantage Point and the Cyclades (Samos, Skiathos, Patmos, Mykonos), and had a great time. We sailed through the Greek Islands on a beautiful ship with an excellent crew. During this time I met some other travelers and found out about their trip "organization". Some people use Titan Tranporter, and others will take the cheaper ferry, but some people will rent a car and find their own way around. There is a big difference in the prices of the ferries and the hotels and spas, so make sure you shop around.

The last day we finished early, spent a few hours in the British Cementery, and flew back to Athens. My hostel, which i booked beforehand, was located next to an American pizza place.

From my hotel I was able to walk to where the boat left from. It was nice to take the boat, but it was cloudy and cold the day of my departure, so I missed some of the scenery I was promised.

The boat back was about a week later, but I took those days to drive around. I started my trip at Athens, then went to Corinth, Kalamata, Mycenae, Lamia, Lithai, and Kassandra.