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Cyclades Islands, Greece

September 2025

By Kelsi

November 23^rd, 2025

Who wouldn't want to spend their birthday on a Greek island, surrounded by sun-bleached stone buildings overlooking the glittering Aegean Sea? (Okay, maybe two days after their birthday, but the rest is true.)

Happy belated birthday to me! In the wee morning hours following my xxth birthday, I slipped into a dark van bound for my 6am flight. I felt like I was fleeing, spiriting myself away while the rest of Seattle slept. And perhaps I was. I was off for yet another adventure—Athens and four Greek Islands in the Cyclades archipelago: Santorini, Milos, Naxos, and Mykonos.

SANTORINI

We can skip my day(s) of travel, which included multiple flights and a quick 24-hour "Part 1" stop in Athens (Athens "Part 2" would occur the next week when the islands trip was over—stay tuned for that).

Instead, we can jump right to the Cyclades. Because wow.

Meaning "circular," the Cyclades are a cluster of over 200 islands strewn across the Aegean Sea. While most of the islands are too small to be inhabited, this archipelago is called the Cyclades because they encircle the sacred island of Delos, the birthplace of Apollo and Artemis.

(In case you're wondering, Delos is the tiny island to the left of Mykonos below the "o" in Ermoupoli.)

Santorini, what a stunning introduction to the Greek Islands and the Cyclades.

The island brimmed with breathtaking and iconic views almost from the moment I disembarked the plane. It quickly became clear why so many visitors flock to this 29-square-mile island every year (nearly 3.5 million, if you were curious).

Something I didn't realize (but made sense upon reflection) was that Santorini has had several other names. Its ancient name is Thera (Thíra), and while this probably means nothing to most Americans, it's huge to me. Back in another life (we're talking 13- to 20-year-old Kels), I wrote and created under the pseudonym Thera. It's the name I chose for myself and the name I loved. Being on this island to (secretly) celebrate my birthday and enter a new and scary decade, it felt both disarming and oddly comforting to cross paths with her again.

Our group stayed in Firá, the modern capital of Santorini. While that may make Firá sound like a large place, it isn't. It's busy with tourists and souvenir shops, but feels small.

Also: delicious gyros stand.

From Firá to Oía

On our first full day, we "hiked" the 7ish miles from Firá to Oía (pronounced "ee-ah," not "oy-ah"). The trek between towns is definitely no hidden gem (the trail can be found on All Trails 😅), but the walk and views are the kind of gem so big and shiny that you can't miss.

Oía is beautiful. The white-washed town looks just like the photos. But it's bright af, for obvious reasons. Bring sunglasses.

A fascinating tidbit (told to us by one of our guides the next day) is that no full-time locals live in Oía. During the off season, Oía is essentially a ghost town. Locals live on "the flat part" of the island—arguably the safer part, since Santorini is a caldera formed by massive volcanic eruptions. These smart folks don't want to fall into the sea (understandable).

This small anecdote planted the "overtourism" seed in my brain, and its vines would follow me all over Greece.

After we walked through Oía, we descended approximately a million stairs to Ammoundi Bay for an incredible lunch with a view, followed by a dip in the Mediterranean. 10/10 recommend.

Up next: Milos

MILOS

Our first Fast Ferry ride was one to remember—and quite different than Washington's ferry system (though both regularly run late):

Assigned seating
Shouty attendants
Maybe 5 cars onboard, with the space to fit dozens more
At least two floors/levels of hundreds of very nice forward-facing seats
Travelers must leave their luggage unattended (I struggled with this!)

The ride from Santorini to Milos was about two hours.

Upon arrival, the differences between Milos and Santorini were pretty clear: less crowded, no cliffside villages, and more adventurous. The main road by the port was lined with storefronts where you could sign up for water-based excursions like sailing, snorkeling, and swimming.

Which was perfect, because that's exactly what we came here to do.

Our group was spread across four properties while in Milos. Not sure how much the other ladies enjoyed their accommodations, but I loved the spot where Wendy and I were roomies!

On our full day in Milos, everyone met up at the port for breakfast and to catch a charter bus bound for Agia Kiriaki (a beach). From there, we boarded our private sailboat to circle a portion of the island, stopping at swimming spots along the way.

What I liked about Milos:

Quieter vibe
The best tuna tartar I've ever had (I ate two bricks at one dinner)
Access to water/beaches (while Santorini had beautiful views of water, we didn't have easy access to it)
Men with names like Leonidas

All too soon we were off for Naxos!

Naxos

Naxos is the largest of the Cyclades, and it was my favorite of the four islands we visited because of its Old Town Market, the working farm we visited, and it's where I ate two of my favorite meals!

Our accommodations were pretty nice, too. Everyone got a room to themselves, but unfortunately I had no hot water. That was not my favorite.

Speaking of bathrooms, something that was a surprise to me when arriving in the Cyclades: You should not flush toilet paper.

Um, excuse me??

But when you think about it, it makes sense. The plumbing on these islands was not built to support the massive influx of tourists. For context: Naxos has ~20k year-round residents, but received 600k+ tourists in 2024. It reminded me once more of (over)tourism and the havoc it wreaks (reeks: pun) on local infrastructure.

But enough potty talk.

In addition to being the Cyclades' largest island, Naxos is also its most fertile, thanks to Mount Zeus, the highest point in the Cyclades, which traps clouds and brings more rainfall. But alas! When I visited in mid/late September, the region hadn't seen rain since March or April!

We were lucky enough to get to visit a local family-run farm. The Basiliko farm has been in the family for five generations. Ana (fifth generation with a 6-month-old baby boy) gave us a tour of the property to see all they produce. I couldn't believe what they're able to grow on one patch of farmland (we only saw a small section). Some of the things I remember: pomegranates, oranges, and lemons; peppers, eggplant, and tomatoes; and olives, of course! They also harvest honey and pork. I was amazed by how they were able to keep things alive despite no rainfall for 5+ months, whereas I should be on America's Most Wanted for the state of my poor houseplants.

During the farm tour, we picked veggies from the gardens and brought them back to the farmhouse to make a delicious multi-course lunch! It was a wonderful time.

In the evening, we explored Naxos' Old Market, which was so charming and filled with color, (cats,) and character.

Without further ado, my two favorite meals!

TOP: (Breakfast) Greek yogurt with every possible fixin'; apple-pear-mint juice; Greek coffee (think Turkish coffee's cousin).

BOTTOM: (Dinner) Naxian salad (capers, tomatoes, carob powder, green onions, naxian cheese); goat ragu.

The next morning, we were off to our final island: Mykonos.

Mykonos

Known for its opulent nightlife and luxurious beaches, Mykonos is an island of contrasts. And to me, it was sadly another example of (over)tourism. The island is undeniably beautiful—the waters a bright sapphire to envy the midday sky—but as we drove from the ferry dock to our hotel, I couldn't help but wonder how much of the island's original charm remains.

On the drive, our guide was thrilled to tell us we were passing Matt Damon's cliffside estate and took us on a detour so we could drive past Lindsay Lohan's "Lohan Beach Club." I'm sure there is a sense of gratitude for American celebrities bringing attention (and money) to their island in the form of tourism. But I wonder at what costs.

On our full day in Mykonos (and our last day of our trip), we visited an abandoned fishing village. I asked why it was abandoned. Our guide explained fishing isn't as lucrative as tourism, so there aren't many fisherman anymore. The land owner is going to turn the area into a bunch of hotels for tourists.

This made me so sad.

And as a literal tourist in Mykonos, I am part of the problem.

We continued our last day exploring the island and visited a small town filled with little shops and bakeries. We walked past an elementary school and it was heartwarming to see the kids at recess. We had a fantastic lunch in a restaurant's brick, cottage-like alcove with a beautiful beach view.

That evening, we watched the sun set at the iconic windmills, which I later learned have been in "idle mode" since the 1800s. But I can see why they were placed there—man, was the wind intense. Dinner was at the steps of the windmills and it was a wonderful sendoff.

—

I loved my time on these islands. Each felt so different, but what was the same across all four was how kind the locals were. I appreciate their hospitality and openness to us loud, bumbling visitors.

It's was hard for me to ignore the impacts of (over)tourism in the Cyclades—from toilet paper to abandoned towns. Maybe it's because I've watched my hometown warp and change into something else, and I don't wish that on anyone.

This archipelago is absolutely magical, and I feel lucky to have been able to experience it and its welcoming locals.

My parents visited Santorini over 40 years ago and were floored by my photos. They couldn't believe how illuminated Santorini was at night. To them, it looked like Vegas :(