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Trip Report

Greek Island Hopping Itinerary

Three weeks island hopping in the Greek Cyclades islands: Santorini, Paros, Naxos, and Andros

by savannah janeAbout Me:Hi everyone! My name is Savannah Jane and I'm all about the outdoors, adventure, and travel. I grew up in a family that was always travelling and it quickly became a big part of my life. In 2017/2018 I did a 9 month solo backpacking trip a... read more

EuropeGreece20 days / August 2017

Highs & Lows

Island hopping in the Cyclades is very easy

It gets crowded during high season (late June to early September)

Itinerary Overview

Greece was my very first stop on my 9 month solo backpacking trip across Europe in 2017/2018. I began my journey in August, which is the peak of high season for both locals and tourists visiting the Greek Islands. It is the hottest month of the year, which means everyone makes their way to the sea.

When I think of Greece, I picture the iconic white and blue buildings, cobblestone streets, bluest of waters, bright pink bougainvilleas at every corner, and amazingly fresh seafood. Greece is one of the most idyllic places on Earth, and the one place that will guarantee I’ll be leaving with a million photos in my camera roll.

For this trip, I was less after the touristy “party islands”, and more in search of the quieter islands that were ideal for hiking, swimming, and exploring. Apart from escaping the crowds, the other benefit in doing this is that the less-known islands are often a lot less expensive.

  • 5 Nights: Santorini
  • Day trip: Oia
  • Day trip: Perissa
  • 5 Nights: Paros
  • Day trip: Naousa
  • Day trip: Marpissa
  • 5 Nights: Naxos
  • 5 Nights: Andros

Q & A

  • What would you have changed?

    Spend more time in Paros, Naxos, and Andros. Each of these islands has a ton of smaller villages apart from the main village, and I would've loved to have more time to visit them all.

  • How was the food?

    The food in Greece is incredible, whether you’re getting a €1 gyros at a stand, or you’re sitting down for a seafood dinner at a beautiful restaurant. Even if you aren't the biggest fan of seafood - Greece is the place to try it because it's the freshest you'll ever have.

  • What tips would you give a friend?

    Most beaches in Greece have umbrellas that you need to pay to rent. My advice would be to go in the morning and pick a nice beach bar or restaurant that you know you’ll want to eat lunch at. Most of the time, if you order food or a drink, you'll get to use the umbrella for free. Just order a drink in the morning and have lunch later on, that way you can keep the umbrella all day.

  • Transportation Tips?

    If you've already been to Athens, try to find a flight directly into Santorini. Athens gets extremely hot and busy in the Summer, so it's worth bypassing the craziness if you can. I had been to Athens before, and didn’t mind skipping it to have more time in the islands, so I found a flight from London directly into Santorini.

  • Booking details?

    For this trip, I booked my hostels and transportation (ferries) as I went. The only accommodation that I had booked prior to leaving home was my first hostel in Santorini. Although it was high season, I didn't have too hard of a time booking just a couple of days in advance.


  • I stayed in Fira, the capital of Santorini, at a hostel called Hostel Kykladonisia. Fira is the most lively village on the island, with a lot going on in terms of nightlife and shopping. The first time that I visited Santorini was with my family back in 2007, and we stayed in a cave hotel. These are quite a bit pricier, but if you have the budget for it - I’d say go for it! It is the most unique experience you will have.

  • I stayed at the Summer Inn Parikia which is about a 15 minute walk from the Paros ferry port and central bus station. The hostel itself was in a great location as it was a two minute walk to Livadia beach and walking distance to the old town of Parikia. It’s also convenient to be near the ferry port and bus station as there are so many little villages nearby worth visiting.

  • I stayed at Soula Hotel, which is a really cute family-run hotel located in Naxos Town (Chora), the largest town and capital of this island. The hotel is located just steps from the main port, the centre of town, and Saint George beach.

  • I stayed at the Lemon Tree Hostel located in Batsi. I can say without a doubt that this was one of the most unique hostels I have ever stayed in. The Lemon Tree hostel is, you guessed it, built into a lemon tree! When you arrive to check-in, the owners, a lovely couple named Miltos & Elena, give you freshly squeezed lemonade. The hostel itself is very airy and open concept, and there is a rooftop terrace where everyone hangs out to watch the sunset each night.