The Ultimate Cyclades Travel Guide – Greek Islands Itinerary

We had such an amazing time in the Greek Islands. The water color rivals the Caribbean and the food is divine. Here’s everything you need to know about visiting the Cyclades.

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When to Visit the Cyclades

The summer months are definitely the time to visit the Cyclades. Many hotels, bars, and restaurants close completely for the winter season. We started our trip in Santorini in mid-September and it was perfect, however by early October Mykonos was winding down. We visited Ios even earlier than Mykonos and it was almost a ghost town!

Aside from things starting to close, in the fall you may potentially experience cool/rainy weather. We lucked out for the most part, but aside from Santorini we had a few showers and chilly days on the other islands.

Getting Between the Islands

You may be thinking of taking a little boat in between the islands, but they are farther apart than you think!

Transportation Options Include:

  • Ferry boat (I mean really big ships. They are filled with cars and some even have the options for beds!)
  • Plane (We flew Ryan Air. Very inexpensive but it’s Ryan Air quality!)

We decided to fly from Athens to Santorini and work our way backwards. I loved doing it this way and would totally recommend it! The flight to Santorini from Athens is just under one hour and super simple.

The rest of our trip we used ferries to get in between the islands. There are a few different companies. We chose the ones that worked best for us based on price and time. They were all about the same.

Funny story: When leaving Santorini we got to the ferry dock early so we stopped at a cafe for coffee. We could literally see our ferry boat. The server told us to chill and that he would tell us when to get up and board. There was an Australian couple eating beside us who were catching the same ferry. We then saw our ferry sailing away! The other couple made a mad dash for it and jumped over the water to get on! It was crazy! We didn’t make it and had to buy more tickets. Talk about an expensive coffee!

The Food in the Cyclades

From casual to super trendy every island had incredible food. You are in for a treat! Ios had the best food in my opinion but the octopus in Antiparos was a pretty memorable meal!

Getting Around the Cyclades

We rented ATVs in Santorini and Mykonos but we rented a car in Paros. We wanted to rent an ATV on Paros too but the rental company said we couldn’t without an international drivers license…yet we could rent a car. (After this trip we actually got international drivers licenses thinking we may need them to ride motos in Southeast Asia. We’ve actually never had to use them!) Seemed like the rental company was in cahoots with the hotel, but it ending up raining a bit so it was nice to have a roof! In Ios we hoofed it on foot and were able to get everywhere we needed to. We also used the public bus a couple times on each island which was fairly convenient and super easy to figure out.

A Breakdown of the Cyclades Islands

Santorini

Santorini was the perfect island to start our trip. It was exactly what I expected it to be… in the best way! It literally looks like a postcard. We stayed in Fira but traveled on ATVs all over the island. Read about our Santorini trip here.

Ios

After an amazing 4 days in Santorini we took a quick ferry ride to Ios. Ios wins for the best food! The overall vibe was great, unfortunately many of the nightlife things were closed given that we were visiting in shoulder season. But we didn’t mind staying in because we loved our hotel here! Check out where to stay and eat in our Ios post here.

Paros & Antiparos

We wanted to stop in Milos after Ios. It is a lesser known island and looked gorgeous. I was really looking forward to it but unfortunately due to inclement weather the ferries weren’t running. Instead we took the ferry to Paros. Paros is super charming and an excellent stop. You can take a simple, small ferry from Paros to Antiparos for a day trip. We loved our day in Antiparos! Read our recommendations for Paros and Antiparos here.

Mykonos

We ended our trip on the party isle of Mykonos. Due to visiting in shoulder season we didn’t get to experience the full Mykonos club scene, but I’m honestly not sure our wallets could have handled it! We still had a blast. Check out what we loved and didn’t love about Mykonos here.

After Mykonos we the long 4.5 hour ferry journey back to Athens, completing our vacation in the Greek isles. It was so lovely and I cannot wait to come back!

On island time,

-Ray

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