Chasing Sunsets Through the Greek Islands

If there’s one thing Greece does exceptionally well, it’s sunsets. Although the food, beaches, wine and ridiculously beautiful little towns aren’t exactly hurting either.

We went in July and somehow managed to squeeze Athens and four islands into nine nights. Yes, we moved around a lot. No, I have no regrets.

The islands are all different enough that every stop felt like a new trip, and with the high-speed ferries, getting between them was surprisingly easy. If you want to see a lot of Greece without taking a two-week vacation, I’d do this itinerary again in a heartbeat.

And somehow, despite all the Naxos cheese and wine I consumed along the way, I actually came home thinner and feeling like a million bucks. That has never happened to me on a vacation. There is definitely something to this Mediterranean diet.

Sunset in Oia, Santorini

Our 9-Night Greece Itinerary

Day 1: Athens
Days 2–3: Mykonos
Day 4: Naxos
Day 5: Paros
Days 6–9: Santorini, split between Imerovigli and Oia

But First, A Word About Packing

Whenever I share an itinerary like this, I know there are people thinking, You changed hotels HOW many times?

Here’s the thing: we only travel with carry-ons.

I love dressing for wherever I’m going, but I care way more about what I’m seeing than how I look while I’m seeing it. I have absolutely no problem rewearing things. I pack pretty much exactly what I need, with maybe one extra generic outfit just in case.

And every hotel has a laundry service if you absolutely need it. I always know it’s there. I have also never actually needed it.

Carry-on only makes this kind of trip SO much easier. There’s no giant suitcase to unpack and repack every other day, no waiting at baggage claim and no schlepping half your closet on and off ferries. We can basically pick up and go to the next destination.

And don’t worry. You can still bring your extra underwear in case of that vacation oops moment. It takes up zero space in your suitcase.

Now, back to Greece.

Athens

Nightime rooftop view from 360 Cocktail Bar in the 360 Degrees Hotel 

After a 10-hour direct flight from NYC, we arrived in Athens ready to take down the Greek ruins. Like tackle the activity of seeing them, not actually tear them down.

Several people told me to skip Athens altogether, but I’m so happy I trusted my gut on this one. You really should see the Acropolis and the other major sites at least once in your life. It’s history, after all.

We stayed at 360 Degrees Hotel, an affordable hotel right below the Acropolis with a trendy rooftop bar and a direct view of the ruins.

We spent a few hours wandering from historical site to historical site and museum to museum before ending up back at the hotel for a drink on the roof as the sun set over the Acropolis.

Temple of Hephaestus.

At the Acropolis in Athens

Mykonos

Did you know Mykonos’ nickname is the Island of the Winds? I did not.

So when I found myself wrapped in a towel and shivering while laying in the sun, I was surprised to learn this was apparently a completely normal occurrence.

We stayed at Myconian Imperial near Elia Beach, partly because of the location and partly because I loved the cute boutique decor. When we stayed, the hotel also offered a free shuttle into Mykonos Town, which made it really easy to go back and forth.

Mykonos was definitely the buzziest and most glamorous of the islands we visited. Beaches during the day, then into town at night for dinner, drinks and wandering around those impossibly photogenic winding streets.

Windmills from Sunset Taverna in Mykonos Town

Elia Beach, Mykonos.

I Scream in Mykonos Town. Bold claim but best ice cream I've ever had. 

Mykonos Town Alleys

Naxos

Next up was Naxos, and this was one of the surprises of the trip.

We stayed at Nissaki Beach Hotel, but what I loved most about Naxos wasn’t really a specific hotel or attraction. It was the feeling of the island.

Naxos completely came alive at night. We would wander through the winding little alleyways with absolutely no plan, stumble upon live music, find a restaurant or bar, drink some wine and keep going.

Golden hour over Naxos

At sunset, head to the Temple of Apollo, also known as the Portara. It’s a massive marble doorway overlooking the sea, and the setting at sunset is gorgeous.

Although I’m pretty sure anywhere in Greece at sunset is gorgeous.

The Portara at sunset in Naxos

Chasing sunsets in Naxos

And we need to talk about the gyros. Greek gyros come stuffed with French fries inside them, which is obviously the correct way to eat a gyro. We ate plenty of these, plenty of Naxos cheese, drank plenty of wine, and somehow I actually lost weight on this trip. I came home feeling like a million bucks, which has quite literally never happened to me after a vacation.

Gyros with the fries exactly where they belong

We only spent one night in Naxos, and if I were changing anything about this itinerary, I’d happily give Naxos more time.

But Paros was only about a 30-minute ferry ride away, so off we went.

Paros

Paros was another quick stop, and we stayed at Hotel Senia near Naousa.

I loved this hotel. It had an amazing pool that seemed to twinkle under the stars at night, an incredible beach right across the street and, most importantly, we could walk into Naousa.

Naousa was exactly what I wanted a Greek island town to be. Waterfront restaurants, fishing boats, little shops, winding streets and endless places to stop for a glass of wine.

Wandering through Naousa, Paros

The twinkling pool at Hotel Senia in Paros

Fresh octopus hanging along the harbor in Paros.

If Naxos felt a little more rustic and spontaneous, Paros felt slightly more polished but still relaxed. I would absolutely return to both.

And then Santorini was calling.

Santorini

We had four nights in Santorini, and instead of picking one hotel, I decided to split them between Imerovigli and Oia so we could experience two completely different parts of the island.

Would it have been easier to stay in one place? Sure.

Did I want to choose between two hotels I wanted to experience? Absolutely not.

Imerovigli

For our first two nights, we stayed at Absolute Bliss Imerovigli Suites, which may be one of my favorite hotel rooms of all time.

The room was huge. The balcony was huge. The hot tub was huge. And the sunset from said huge hot tub was ridiculous.

There was also an amazing pool just steps away from our room that basically felt like our own private pool because somehow we were always the only ones there. And, as with pretty much everything in Santorini, it overlooked the caldera with ridiculous views. We honestly didn’t need to leave the hotel.

Give me a glass of wine, that balcony and a Santorini sunset and I’m good.

Sunset over the Santorini caldera from Absolute Bliss

A pool with a caldera view

Not a bad place to watch the Santorini sunset

Santorini by Boat

One of the best things we did on the entire trip was a day with Santorini Yachting Club.

We sailed around the island, swam in the volcanic hot springs, stopped at the white and red beaches and had a BBQ on board.

Seeing Santorini from the water is completely different, and swimming off a boat in the Aegean Sea is about as good as vacation gets.

I would absolutely put a boat day on any Santorini itinerary.

Yacht BBQ

Floating somewhere off the coast of Santorini

Much prettier than it looks in a photo but did smell like sulfur…

Santorini by ATV

We also rented an ATV and drove around the other side of Santorini, including stops at the black sand beach and red sand beach.

Touring Santorini by ATV

It was a completely different side of Santorini from the picture-perfect cliffside towns you see in every photo, and one of my favorite ways we explored the island.

Black sand beach in Santorini

Red sand beach in Santorini

Oia

Rush hour in Oia

For our final two nights, we moved to Atrina Traditional Houses in Oia.

Oia is the Santorini you’ve seen in a million photographs, and somehow it still manages to be even prettier in person.

Whitewashed buildings spilling down the cliffs. Blue-domed churches. Tiny stone pathways. Donkeys making their way through town.

And those sunsets.

The blues of Santorini

Yes, Oia gets crowded at sunset. Yes, everyone is there trying to take essentially the same photograph. And yes, you should still do it.

We got to Oia early for sunset, claimed a spot and brought a bottle of wine with us. This is one of the touristy things I would absolutely tell you not to skip.

There’s something kind of magical about a group of people gathering on the side of a Greek island just to watch the sun go down. The second it disappears into the sea, everyone starts clapping. It sounds a little cheesy but in the moment, it was actually weirdly emotional.

Crowds and all, completely worth it. Possibly thanks to the wine.

The reality behind the perfect Oia sunset

Get there early and bring the wine

And this is why everyone comes

Would I Do This Itinerary Again?

Absolutely.

Nine nights. Athens. Four islands. Multiple hotels. A lot of ferries.

For some people, that probably sounds exhausting. For me, it was the perfect way to experience Greece.

Every island felt different enough that I was excited every time we got off another ferry. Mykonos had the buzz. Naxos had the winding streets, live music and food. Paros had Naousa and that laid-back waterfront feel. And Santorini was every bit as beautiful as I hoped it would be.

One last Santorini sunset

Come for the islands. Stay for the sunsets.

And apparently eat all the cheese and drink all the wine you want, because you’ll somehow look even better than when you started.