The Ultimate Itinerary for 14 Days in Greece

So you have two whole weeks set aside for a getaway… and you are looking for the perfect itinerary for a dream 14 days in Greece? Look no further. The itinerary I developed for Greece rates as one of the best I’ve ever planned and organised.

Greece is BIG! The groups of islands are very spread out and there are clusters or groups of islands that each offer a different experience. And while a 14 day itinerary is a generous length of time, you certainly can’t see it all. Better to pick a few destinations and get the best out of those islands right?

The Cyclades group of Islands in Greece delivers a little bit of everything… read on and you’ll see what I mean.

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Let’s Get Started…

Before I holiday, I plan. Don’t get me wrong, I love spontaneous holiday experiences and go with the flow itineraries. But not all destinations are suited to this easy going approach. Greece is definitely one of these destinations (unless of course you have an unlimited timeframe then for sure, sit back, relax and follow your nose). However, for most travellers visiting Greece, there are a set number of days scheduled. And therefore you’ll be needing some kind of guide or itinerary to see the best bits. But where to start? So many islands, and each so different with a new set of things to offer. The following itinerary for 14 days in Greece is the best I’ve developed and I want to share it with you.

This itinerary includes a perfect balance of beach time, private sailing, relaxation, and shopping and nightlife if that’s what you’re looking for. There are also links to our accomodation recommendations that are somewhat off the tourist trail. And the budget… midrange.

Just a note… Greece is expensive! But don’t worry, this itinerary won’t break the bank.

Mykonos

One of the most commonly asked questions by visitors wanting to see the Islands, but also Athens… which order to do it in? A word of advice, keep Athens till the end of the trip. This is because ferries can be slightly unpredictable at times with unforeseen weather conditions. So fly in and think about flying straight to the islands.

Our experience flying with Aegean Airlines for all internal flights was great. Flights were on time and luggage arrived… so ticked the boxes for us.

Now chances are Mykonos is on your list. And rightly so… it is quintessentially Greece. That look of white and blue, stoned streets, pink flowering bouganvillea trees… you know what I’m talking about. It is a total tourist trap, but it’s beautiful and you really can’t miss it. I’d recommend this as a good place to start for a couple of nights, just to get you settled into that feeling of Greece.

Sailing

Picture this for a second, sails up, cruising the open sea, arriving at a secluded beach and anchoring up. Then spending the afternoon completely alone, free to swim, walk the beach, nap and sunbathe… your own Greek Island… all to yourself! Yup… it doesn’t get any better than that my friend.

Now this might sound like a luxury, but how often do you get to visit Greece? I scoured websites for sailing options through Greece and came across MANY! But only one that I would recommend.

After many emails back and forward with sailing operators, I finally found one provider. This provider was very experienced, helpful in terms of recommendations, totally reasonably priced and the best part… it was just the skipper and us on the boat. It gave us space to truly get off the tourist trail.

We were picked up from Mykonos and visited Tinos and Syros, two uniquely different islands. And beautiful! Another post of this coming soon.

Ultimately, spending a couple of nights on a yacht with a skipper that hand picks sights and islands to suit your individual preferences is the stuff that makes memories. You’ll visit empty beaches, anchor up at a quiet picturesque bay for an evening and explore islands off the beaten track. There is also something quite special about docking up in the centre of town with bars and restaurants at your yachts front step. Do it! You honestly won’t regret it.

Paros

Shake the sea legs off and settle into an Airbnb for a few days on this beautiful island. We recommend Villa Aspries. For location, comfort and autonomy it does’t get much better. This gives you the chance to catch up on some washing and to cook a few meals with the amazing Greek produce that you’ve picked up along the way.

Grab a rental car and explore, everywhere you can. Take a good book, work on your tan, find a pretty beach, eat greek food and eat some more. There is so much to share about Paros that it deserves it’s own dedicated post. The island was a total gem with so much to offer.

Santorini

It’s time to get ready for the tourists again. Catch a fast ferry with Seajeats to this famous island reserved only for the romantics. Or so we were told… Honestly, it was nothing like we expected. Yes sure, tourists everywhere all trying to get that perfect Instagram shot. But it’s very easy to side step that scene with a few simple tips. Before you know it, you’ll have broken away from the masses. This however, also reserved for another post.

There are so many great places to see and explore in Santorini. Check out this dedicated post on Santorini. But for accomodation, look no further than Oia. We recommend these amazing traditional cave houses – Zoe Aegeas. While all the hundreds of tourists line up shoulder to shoulder for the ionic sunset photo of Oia, you’ll be sitting on your own private traditional balcony sipping a chilled glass of Santorini wine. Oh yes! Did I mention the wine? They do wine very very well.

Athens

Time is running out now, so we recommend a flight from Santorini back to Athens. Take an early morning flight so you can make the most of all that Athens has to offer.

Get your walking boots on. The accomodation we recommend below in the itinerary overview is city central and walking distance to most places.

Our favourite sites included –

• Theatre of Dionysos and Odeon of Herodes Atticus
• Acropolis
• Acropolis Museum
• Areopagus Hill
• Roman Agora and Tower of the Winds
• Ancient Agora
• The Monastiraki Flea Market

Top tips for Athens: Get to the Acropolis early. We were the first there in the morning and enjoyed the cooler weather and more contained crowds.

Tips

When to visit – If you can, September. The school holidays for Europe have finished which means peak season and prices have also. The weather is slightly cooler. But note that by October and November some places are beginning to close and Greece is very seasonal.

Travel light – Island hopping means packing and unpacking. We prefer to backpack and in places such as Mykonos and Santorini this is going to pay off. If you’re staying in central locations such as our recommendations below, then cars are restricted.

Book ferries in advance – This secures a place for you on the ferry, because trust me they get very busy. It also gives you a better understanding of itinerary.

Travelling with Kids – Follow this link to see our full dedicated post to travelling Greece with kids.

The Complete Itinerary to 14 Days in Greece

Anastasia’s Visage	3 nights in Mykonos – Fly Direct with Aegean Airlines
Mykonos Onboard	3 nights sailing trip – Departing from Mykonos to wherever you choose! Tinos and Syros recommended
Villa Aspries	5 nights Paros Airbnb – Mykonos Onboard deliver you directly to Paros
Zoe Aegeas	2 nights Santorini – Ferry from Paros
Alice Inn Athens	1 night and 2 days Athens – Early morning flight from Santorini with Aegean Airlines

For further information related to the places we visited then stay tuned. I’ll be sharing the highlights of Greece in more detail. These posts will explore how to get off the tourist trail in Santorini, the highlights of Paros, the benefits of Sailing the Cyclades, and travelling Greece with Kids.

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To hear more about our travel story and upcoming plans to travel the world full-time, then you might like to read this post. Find out how Covid 19 has halted our dream adventure in 2020, and what comes next as we plan to leave Dubai (our current home) during these uncertain times.

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