Greek Island Hopping: Cyclades Itinerary

In 2015 I went on a Greek island hopping adventure with my best friend. We did it in a very spontaneous manner, having simply booked a return flight and nothing else before arrival and it turned out to be perfect! Here’s my story of my Greek Island hopping itinerary:

London – Athens – Santorini – Ios – Paros – Naxos – Athens – London

Perissa Black Sand Beach, Santorini

FLIGHT: Athens – Santorini

Santorini is a truly idyllic area, and the two sides of the island completely contrast each other. On one side, you have a glittering black sand beach surrounded by hotels, hostels, restaurants and many other amenities. Whilst the other side of the island offers true luxury, where you will find the private villas and beautiful pools that you’ve likely spotted whilst skimming through Pinterest. There is so much to do in Santorini, whether you want to enjoy an early morning yoga session, take a trip to the water park, brave it on a quad bike and ride into the sunset or partake in some water sports. You can make your trip as action packed or relaxed, as you like!

A hotel with a pool near Perrissa Beach, Santorini

We stayed on the black sand side of Santorini having taken the bus into Perrissa and found somewhere to stay very quickly, and with a budget of €20 a night each, we found a lovely hotel (with a pool) that was just two minutes away from the beach. Santorini is a perfect place to start our trip, the food was delicious, and the views are incredible.

Tip: You can fly directly to Santorini to save travel time, or take the ferry from Athens to the first island (I’d recommend starting with Naxos)

Views into Fos, Ios from the top of a hill

FERRY: Santorini – Ios

After Santorini, we got on a ferry to Ios! The party island of the Cyclades, Ios is a complete change from the slow pace of Santorini. We were meant to stay three days but had far too much fun to leave, so ended up there for five days. Ios was the life and soul of the party during our trip, although not as well known as places such as Kavos and Ibiza, Ios was a lot less tacky and more enjoyable. The quaint streets in the town of Los were beautifully empty during the day, and you could happily get lost wandering around, stopping off at the local bakery for a snack of sweet baklava. Then in the night, Ios comes alive with people out to party, there is a vast range of places to go, each offering something different! Mylopotas beach is just a 20-minute bus drive away from where we stayed, where we enjoyed a few days sunbathing and a pool party at the Far Out Beach Club! Again, we easily found somewhere to stay at the port, and they offered us transfers both ways within budget.

Tip: Don’t be put off by the hotel owners at the port trying to offer somewhere to stay, it can be overwhelming at first, but this is the best way to negotiate a price and find somewhere nice!

Our camping adventure in Paros with a tent and a washing line

FERRY: Ios – Paros

Leaving Ios was very emotional; we could have easily spent the entire summer out there, however, after 5 days we had to move on to the next island. Paros was the next destination on our itinerary and a feeling little deflated from leaving our favourite place it was a rather calm few days, we camped near Krios beach for one night and had to cope with some… interesting campers. The less said about them, the better! The other two nights we stayed in quite a large hotel complex a few minutes down the road from the beach, which was near some lovely restaurants. Paros was lovely, and still picturesque in its own way, however, if I were to do the trip again, I would probably take a trip to Mykonos instead. It was the only place on our trip that I didn’t fall in love with.

Tip: Sleeping on a lilo in a tent may seem like a great idea to begin with, however, when the weather is hot it makes for quite an uncomfortable nights sleep!

Beautiful waves crashing over the rocks at Sunset in Naxos

FERRY: Paros – Naxos

Naxos was the final island on our trip and personally, I would say, the most beautiful. We stayed fairly close to the port, and there were so many beautiful beaches within walking distance as well as crafty shops, markets and other amenities. The beaches there were just sublime, and the sunset-watching spots were endless! Whether we were sat upon a set of rocks watching the waves crashing, or hidden in a small sandy cove, the sights were incomparable to anywhere else in the world. As this was the last stop on our trip, we took it at a very leisurely pace. We spent the days sunbathing, enjoying ice creams and wandering through the streets, while the evening was spent enjoying the delicious Greek food and watching the sunset. The locals here were amongst some of the friendliest people we’d met, and were always willing to help you to get the very best out of your trip. Naxos was the perfect finish, and somewhere I would definitely visit again in the future.

Tip: The nicer you are to the locals, the nicer they will be in return. We made friends with the couple who owned a nearby shop, and they offered us free fresh vegetables and rolls to cook with our meals almost every day! We made them some origami flowers before we left as a thank you.

Beautiful waves crashing over the rocks at Sunset in Naxos

FERRY: Naxos – Athens

Three weeks seemed to pass by far too quickly, but it was one of the most incredible experiences of my life. The challenge helped to grow my confidence and fuelled my passion for travelling. I was amazed at how easy it was to find accommodation at the last minute, even on a budget! There wasn’t anywhere we stayed that was sub-standard. The food was delicious and inspired me when I returned home. I would definitely recommend island hopping as an alternative holiday or travelling adventure!

sunset over the Cyclades cluster of islands in Greece

Travel tips:

  • Plan out your island route and do a little research into the islands a little before setting off.
  • Pack as light as possible, as there’s nothing worse than having to carry around a massive. backpack filled with ‘just in case’ items.
  • Live like a local, whether it’s buying from the local shop or asking for recommendations, no one knows the area quite as well as those who live there!
  • Wear suncream and reapply, reapply, reapply. Burning my eyelids did not make my holiday any more fun and it hurt for days!
  • Embrace every opportunity; although something might seem scary at first, you’ll only regret not doing it in the future!

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24 Replies to “Greek Island Hopping: Cyclades Itinerary”

  1. I loved this post with lots of travel tips, I’m looking to travel more when I have enough money saved up in the future and this has definitely helped me if ever I want to go to Greece 🇬🇷

  2. Lovely trip you did! I’m surprised that Naxos is more beautiful than Santorini. I had the privelege to stay on the luxe site of the Island as my two nephews work in one of the best hotels on the Island. I would go back right away! You made me curious about Naxos though..
    Thanks for this post!

  3. I love island hopping! The cyclades are perfect with stunning views at Santorini to watching beautiful sunsets at Naxos. This is now on my list and am saving your itinerary!

  4. Great post with very helpful tips and amazing photos! Waves crashing on the shore with sunset at the backdrops is stunning! I would love to visit this place. Greece is my dream-destination. 🙂

  5. What a great itinerary. I have only been to Mykonos and Santorini but would love to check out some of these islands as well. Good to hear you loved Ios so much and that Naxos was so beautiful.

  6. I have always wanted to go to Greece. I taught World History, and it really made me want to go. I also love beautiful landscapes and culture, and Greece sure has that. Love the look of that water!! Appreciate the travel tips.

  7. Such a beautiful itinerary. Looks like the trip of a lifetime. Wish I can take two weeks off to head there too. Santorini and Paros rank high on my list. Cheers!!

  8. That looks amazing!!:) I’m going to Santorini in 2 weeks, so thank you for sparking even more excitement with this post! I would love to do an island hopping tour, but it’s just me, so I thought that just staying in Santorini would be enough for this time. Next time though:) Your photos are awesome because they show the different islands in their diversity:)

    1. Thank you! Aw I hope you have an amazing time! Santorini has so many beautiful things to see so I’m sure you’ll have a fantastic trip!

    1. Hi Margareth, oh wow, hope you have a fantastic time! Where abouts in Greeece are you planning to travel?

      We stayed in a couple of hotels there, one was called Tranquilo and they did the yoga lessons and had a really lovely bar/restaurant but I cannot remember the first place.. It was opposite a hotel near Perissa if that is any help!

      Thank you so much!

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  10. I’ve totally been wanting to go back to Greece! This is super helpful, I loved the tips at the end, pinning this for later.

  11. I LOVE LOVE LOVE that you went to Perissa!! It is my favourite place in the world, I actually lived there for three months (about 2 minutes walk from your photo actually! haha) I love Naxos (and Naxian Cheese <3 <3 <3), we were in Ios in October so it was mega quiet! haha

    Think I have to hit up Paros next, complete your itinerary 😛

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