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10 tips to plan an amazing trip to the Greek islands

Our week-long trip to the Greek islands was wonderful!

10 tips for planning an amazing trip to the Greek islands

Here are the top tips I share with anyone planning a trip there:

  1. Find a cheap ticket! 
    My ticket from Seattle into Mykonos was $422! Thanks, Scott’s Cheap Flights! Greece flights seem to go on sale often enough that if you’re flexible with your timing, you could get a similarly smokin’ deal.

    The Mykonos habour at sunset.
  2. Fly into the islands.
    I’d love to go to Athens and other areas on the mainland, but this trip was about the islands and I’m so glad I had a 45 minute flight from Athens to Mykonos instead of an overnight ferry. More island time! Not all islands have airports, but most of the major ones – more than 15 – do.
  3. Pick which islands you want to go to. This time.
    There are 6,000 Greek islands! They all have their charms, but you just can’t get to them all. Pick an island group – we went to the Cyclades – and then pick a few islands. I used Lonely Planet’s guide to learn about each island and help me pick. This article from CNN highlights a few great options too. The bad part is, basically any island I read about, I wanted to go to! So, just pick, enjoy, and repeat!

    Paros is a lovely fishing island community.
  4. Create an itinerary that is realistic.
    You’re in Greece, you want to maximize your time, but truly what maximizes your time is spending long enough on an island to fully enjoy it, not going to as many as possible. We did three islands (Naxos, Paros, and Mykonos) in 10 days and that was just on the edge of too much moving around. Two would have been great too!
  5. Ferry between the islands.
    The ferry schedule had some influence on where we went. We picked islands that were a short ferry ride away to not waste too much of our vacation time traveling. Episode 13 of the Bold Departures Podcast talks about navigating the Greek ferry system.
  6. Be flexible.
    If you are going during off season (we went in the shoulder season late-August to early-September), stay open to possibilities. You may LOVE one island and feel like you want more time there. On our sailing trip we spent an afternoon on Koufonisia and it was so amazing, I’d have loved to spend more time there! You may meet people and hear about other islands they’ve enjoyed and want to change plans. The exception is, if you are going during high season (July and August) and have your heart set on a certain island or hotel, book in advance.

    View from a cute bar on Koufonisia – the prettiest blue water we saw the whole trip!
  7. Go to Naxos! And probably Amorgos. 
    If you’re in the Cyclades, my favorite was Naxos, so that’s where I tell people to go. We talk about it also in episode 13. Emily enjoyed Amorgos on a past trip with her brothers (hear a little about that in episode 9) and it was recently featured by Condé Nast as the exquisite little island you’ve probably never heard of but will be glad you did. Also on my hit list for next time – Crete! We heard wonderful things about Crete.

    From our hotel in Naxos to the beautiful beach.
  8. Eat Greek salad everywhere.
    Each restaurant has their own take on this deliciously fresh salad and each island has their own cheese to top it with. We ordered it every lunch and dinner and never got sick of it. Hear about the other great food we ate – and made! – in Greece in episode 14.

    One of the many Greek salads consumed.
  9. Plan adventures and “plan” downtime.
    I wanted my time in the Greek islands to be relaxing, but authentic – not just something I could do with a quick flight down to San Diego. We did a hike, a cooking class, an archaeological tour of Delos, a sailing trip, and checked out the sights on each island…but still made sure we had time for reading on the beach, drinking on the patio, and enjoying relaxed meals. It was a perfect balance.
  10. Learn the basics of Greek.
    We had no communication issues at all on the Greek islands, but learning how to say hello, good morning, good night, thank you, and please is just good practice for any trip to a new country.  My regret is not using it very much because it felt uncomfortable, but it’s appreciated, so just try!

ευχαριστώ (efharisto or thank you) for reading my tips for traveling to the Greek islands. Check out our full album of photos from our trip on the Bold Departures Podcast Facebook page.

Just remembering the trip and writing about it makes me want to go back ASAP! In the meantime, tell me all about your travels in the comments or email us at bolddepartures [at]!


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