Greek Islands

So, you’re planning a vacation in the Greek islands, but not sure which of the 250+ to visit?

I felt overwhelmed researching our first trip. Friends inputted, “Mykonos is a must!” “Santorini is the BEST!” But are they worthy of the hype or is it just where a travel agent or their cruise sent them? Is Mykonos vs the other islands the touted overrated equivalent of Times Square vs other neighborhoods in Manhattan, in which case I definitely don’t want to stay there?! Oh, the things that keep me up at night…

The islands are organized into groupings, which can help as you narrow down the choices. I knew one island HAD to include that postcard-perfect clifftop village with brilliant white abodes and blue domed churches because… have you truly experienced the islands if you haven’t gazed that gazely stare? That said village would be Oia in Santorini which for me determined the Cyclades islands.

Corfu had been in the mix — have you seen the fabulous series: The Durrell’s in Corfu??!! But travel would eat up basically an entire day. Crete as well. Hoping those will make an appearance in future travel plans. After research and careful consideration of other Cyclades islands, Milos and Naxos joined my planning party.

So how did the choices fare? Honestly, though… can one even make a bad pick from this pocket of heaven set within the Aegean Sea?

Oia, Santorini

Santorini

Glamorous? ABSOLUTELY! Crowded? VERY! Expensive? INDEED! Santorini truly was wonderful in many aspects, but I don’t really feel the need to return. I would still highly recommend a short visit as this island offers a feast of pleasures, especially for the eyes.

The good:

That gorgeous sunset view over the city of Oia or a nearby sailboat… perhaps the best I’ve ever seen. There is even a nightly gathering at all the best viewpoints to celebrate it, with applause erupting at the finale. Charming the first evening, ostentatious by the 4th.
our AirBnb location, right on the water below Oia. Away from the crowds and it came with a boat/captain who would whisk us over to Ammoudi Bay where we could dine or access our rental car at whim.
Sunset sail
Picture perfect
Ruins
Wineries

The bad:

Crowds of tourists
Expensive
Forced perfection of the white-washed town. If Disney had created a Greek island, it would be Santorini. For some this will fall into the good list;)

Click here for more information and recommendations on Santorini. (COMING SOON)

Milos grotto

Milos

Milos aligned well with my imagined perfect Greek island, with small villages, water-side restaurants, gorgeous beaches, and friendly locals. The coastline is very dramatic — one must also see it from a boat to truly appreciate it completely.

The New York Times published two fabulous articles on Milos which turned me onto this island — this one with it’s overview and this one which beautifully captures the vibe. From 2019, but I think they still ring true, though I keep hearing that Milos may soon give its more famous neighbors a run for the money as the stunning instagram shots pile up.

The good:

Gorgeous beaches
Fabulous restaurants
Sailing around the island. The scenery is spectacular.
Easy to get around everywhere via scooter or car.

The bad:

Cannot think of one single thing

Click here for more information and recommendations on Milos.

Chora, Naxos

Naxos

Naxos is the largest island in the Cyclades — we stayed here for 5 days and didn’t even scratch the surface. It really has something for everyone. A beautiful hilly interior dotted with sheep and picturesque villages, spectacular sunsets, stunning beaches, a medieval city, and ancient ruins as well.

We stayed inland here, in the most charming whitewashed village, Filoti. Our Airbnb house sat at the top of this vertical town, with views extending over the surrounding hills all the way to the sea. The downside was the uphill maze-like walk back home after dining or shopping downtown, the upside being the views and the caloric burn trekking up and down each day.

The good: