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A Plan to Island Hop in Greece

It’s almost all set – Greece is happening!

A real adventure is mapped out and we couldn’t be more thrilled to get going. It’s a little bit of a process to work out exactly how to navigate Greek islands and get the most from your trip. How do you decide which Greek islands are worth visiting? Are some over-hyped and some hidden? How is Greece is the off season? How much olive oil can I bring back with me in a suitcase?!

Greece skyline at night

Yes, these are all pressing questions. To prepare for the upcoming excursion, here’s the rough plan of a two-week itinerary. It could easily be modified into a week, or exclude some of the spots all together. Let’s do this!

Fly into Athens

Flying into Athens is the easiest way to start in Greece. The airport is a large hub and the city itself is worth spending a few days in. They have direct flights from most other major European cities and worldwide destinations. It’s about a 20-minute taxi ride to the main ferry port to reach other islands from there as well.

Athens columns

Fly out of another Greek Island

I found going in and out of London, it was comparable to book two one-way flights. This way I wouldn’t have to make my way back to the capital and could take a one-way route instead. So, flights into Athens, then flight out of Santorini back to London. Easy peasy.

All the Greek Islands in Between: Itinerary

Once the touchdown in Athens is complete, a few days are spent exploring the city and many of it’s ancient attractions. From there, a car rental will give freedom to move about the mainland. Then I’ll visit two islands and head back to London.

Day 1-2

Fly to Athens, explore the city a bit! I’ve never been to Greece and look forward to the trip. I’ll meet a friend’s parents who I’m sure will show off their amazing cooking skills and neighborhood.

Day 3-5

Greek islands blue water and sands

Drive to smaller villages and towns, including Monastiraki, Nafpaktos and Chania-Trizonia where there’s a recommended amazing fish restaurant. The experience will include a lovely homestay with a dear friend’s family home in the village.

Day 6-10

A few hours from the towns is the port of Pireaus, where many of the ferries go to reach the islands. I have a very early ferry to catch to the island of Paros after dropping off the car. I booked ahead of time through Open Seas, which was simple to use and gave a list of all the routes with various ferry companies.  In Paros, I am graciously hosted by a gorgeous and spacious Airbnb owned by Asterios and his family. I’m thrilled to have the opportunity to explore this less tourist-centric island.

Pireaus white and blue home

Day 10-13

The final stretch is Santorini! I will take another ferry from Paros to Santorini, which is about 3-4 hours with a few stops in between. I thought it was worth purchasing online ahead of time to make thing easier, as with the Pireaus-Paros route. In Santorini it will be relaxed as the season winds down, with us staying at the beautiful Vedema Resort in the small village of Megalochori.

Greek-Style giveaway with Miss Tunica

If you want to be transported to sunnier skies along with me, on Pure Wander we’re offering a giveaway with Miss Tunica – open worldwide! The winner will have their choice of garment (pending availability) from their luxury line of tunics, dresses, kaftans and beach cover-ups. I’m obsessed with mine and can’t wait to wear it in Santorini.

Take a look at these beauties (I have the one on the right!):

Miss Tunica dress


Feel free to enter below multiple ways, or go visit us on Instagram to find a few more bonus entry options!

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tunic kaftan giveaway miss tunica and pure wander open worldwide

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel writer, social media manager and owner of Pure Wander. She's been to more countries than your kindergartner can count, and she's our resident expat extraordinaire. Follow her on Twitter @Crooked_Flight

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