Cyclades Island hopping in Greece – The Ultimate 3-week Itinerary

Cyclades Island hopping

In this blog post we are sharing our exact Cyclades Island hopping Itinerary that we made. The Cyclades Islands are a group of about 220 Islands in the Aegean Sea. They have the most picture-perfect greek towns; for us, it is one of the most romantic places we have ever visited. The most popular islands are Mykonos and Santorini, but the Cyclades Islands have much more to offer. This 3 week’s island hopping itinerary is a trip we dreamed of for a long time, and it was probably our favorite euro summer trip ever.  Continue reading to find out all our favorite islands and why we love them to help you plan your perfect greek summer trip.


Best time to visit the Cyclades Islands

The best time to do a Cyclades Island hopping trip is from May to October. July and August are the hottest and high seasons, meanings most visitors to the island.

We recommend visiting May/June or September/October for better prices, fewer people, and great weather. We prefer the shoulder months and visited the Cyclades Islands, Greece, in September, which was perfect. Typical sunny weather but not too busy.

How to get there

Our ultimate three weeks Itinerary for Cyclades Island hopping in Greece starts in Santorini, which has a small national airport. Depending on which island you start your trip to, you can fly to your first destination directly or get to the island by ferry. We flew to Santorini with a stopover in Athens. 

Oia Santorini

Cyclades Island hopping – the ultimate 3 weeks Itinerary

Day 1 – 4 Santorini

Santorini is the most popular island of our 3-week itinerary and therefore can get very crowded in the high season. But still the island is well worth a visit. Santorini is a very speical island with its beautiful white towns built on the side of the dark cliffs and the view of the blue water of the Aegean sea. 

Don’t worry about the crowds there are still ways to enjoy the island without them and you will find all our tips in our ultimate off the beaten path Santorini travel guide.

Day 4 – 7 Naxos

Naxos Island is the one that surprised us while Cyclades Island hopping in Greece. It’s the biggest island of the Cyclades and a very diverse place to explore. We felt that Naxos is a very cultural, culinary, and authentic island. It also had the most beautiful sandy beaches. Naxos quickly became one of our favorite islands to visit.

Check out the 10 must-do things when on Naxos Island, our complete travel guide for this island.

Day 7 – 12 Paros & Antiparos 

You get two in one when visiting Paros and it’s smaller, wilder sister  island Antiparos. Paros is the dreamiest of the Cyclades we visited. We loved exploring the picturesque towns with all the colors and flowers and the island’s beautiful beaches. There is a lot to do in Paros, and our ultimate guide, we share all our top tips for the best places to eat and stay and the 10 most amazing things to do in Paros.

Day 12 – 15 Ios

Ios is one of our favorite islands of the Cyclades, and we would go back in an instant. To be honest, we didn’t have huge expectations for Ios because so many people said it’s the party island, which might be accurate. Still, it has so much more to offer, and in our opinion, it’s totally underrated. It has so many empty beaches and off-the-beaten-path places to explore and adventure. Not to mention the incredibly clear and blue water everywhere. It was way less busy than other islands in September, and we loved that.

Make sure to check out our 9 most amazing things to do in Ios

Day 15 – 21 Milos

Milos Island gained much popularity in the last few years, and we can understand why. We didn’t get bored for a second while in Milos as there are so many amazing things to do on this island. For us, it was a perfect combination of relaxation and adventure. Milos quickly became our favorite island of the Cyclades Island hopping Itinerary. It offers much, from beautiful beaches, places to adventure and pretty Greek towns with fantastic food options. 

Check out the 10 most amazing things to do when visiting Milos

How to get around between the Cyclades Islands

Some of the islands have small airports, while others don’t. The best and most affordable way to Cyclades Island hopping is by local ferry. We used the website and app of ferryhopper and found it very convenient. We recommend pre-booking your ferry tickets, especially in the high season.

Budget for traveling in Greece

The following budget helps you to plan your Cyclades Island hopping trip. Of course, the costs can vary depending on the accommodation, for example.

  • Price per night for accommodation: 60.00 – 150.00 Euro per night (budget to midrange)
  • Cost for two meals per day for two people: 60.00 – 80.00 Euro per day (for lunch and dinner)
  • Cost of scooter or car rental: 20 – 50 Euro per day
  • Ferry Ticket to travel between the islands: around 50 Euro per person (depending on which island)
Naousa Paros

Travel tips

Internet Access

We recommend buying a local SIM card for the cheapest and most reliable Internet connection while Cyclades Island hopping in Greece. We sometimes had bad connections in our Airbnbs.

The most convenient option for travelers is the eSim Card (digital SIM card) from Airalo. You can download and install a digital data pack and get connected anywhere in the world as soon as you land, so there is no need to waste time looking for a local plastic SIM card. 


Greece is undoubtedly one of our favorite European countries, and Cyclades Island hopping was a big dream coming true for us. We love the picturesque white towns full of flowers, cute taverns, streets full of cats, and Mediterranean food. The highlight for us was the incredibly blue and clear water and all the stunning beaches we found during our trip. It’s hard to choose a favorite island as they all had something special we loved most. But if we had to choose, we think Milos has the best mix of everything. 

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