Greek Island Hopping: Chaos, Calm & Cold Ocean Water

I wasn’t sure what to expect with Greece… but I knew it would be special. This was my first big international trip with my best friend Madeline, and we were ready for the adventure. We booked our flights, packed light, and gave ourselves permission to wander. What followed was two weeks of ferries, late sunsets, ancient ruins, cold ocean water, and a whole lot of unexpected moments (good, awkward, and hilarious).

From Athens to Mykonos, Naxos, Santorini, Folegandros, and back to Athens again—every island felt like its own world. And every stop gave us something new to laugh about, reflect on, or just sit with in silence. Here’s how it all went down.

Mykonos: Wild Streets, Kind People & One Unexpected Nudist Beach

The energy in Mykonos hits fast. Think: maze-like alleys, whitewashed walls, and no street signs. I learned the alleyways were designed to confuse invaders—which explains why even locals still get lost. (And yes, Madeline and I absolutely got turned around more than once.)

We kicked things off exploring Mykonos Town, watching the sunset in Little Venice, and visiting the ancient island of Delos by boat. The ruins were beautiful, and the view from the top was next level.

Then came Paradise Beach, which we learned (a little too late) is a full-on nudist beach. Let’s just say we were not prepared for the… visuals. Everywhere. Despite the surprise, the beach vibe was still amazing. Great music, clear water, and a fun, carefree energy that set the tone for the rest of the trip.

Oh—and Greek men? Gorgeous. But heavy smokers.

Naxos: My Favorite Island, Hands Down

If Mykonos was the party starter, Naxos was the breath of fresh air. The people here? So warm and genuine. The food? The best I had in Greece. And the energy? Completely chill and unbothered in the best way.

We wandered through Old Town, found ourselves in random local conversations, and stumbled into the Venetian Castle. I’ll never forget the massive Portara, a marble gateway that towers over the harbor. It looks like something out of a fantasy movie—just standing there alone, facing the sea.

At one point we got a little lost (again), ended up at a police station, and were greeted by a very attractive Greek officer who tried to explain the ruins to us. According to him, the temple was destroyed by an earthquake and that’s all that remained. Cute story, but no. Turns out the temple was actually dismantled during castle construction—but the doorway was too big and heavy to move, so they left it. And now it just stands there, bold and stubborn, like it’s still waiting for something.

Naxos also came with one tiny hiccup: an older man in a red pickup who decided to stalk us for a bit. He didn’t ruin the experience, but it’s a good reminder to always stay aware—even in the friendliest places.

Still, Naxos was easily my favorite island. The vibe, the people, the pace—it all just felt right.

Santorini: Pretty Views, Petty Vibes

Santorini was the third island we visited. And visually? It delivered. The cliffside views. The white domes. That glowing caldera at sunset. I mean, wow.

But… the attitude? Not so pretty. By day four, we were over the rudeness. Madeline and I looked at each other like… is it us? (Spoiler: it wasn’t.) There’s only so much yelling and pointing you can take before the vibe shifts.

We still soaked up what we could. We walked through Oia, explored Akrotiri, and dipped our toes into Kamari’s black-sand beach. We even took a boat tour to Nea Kameni, a dormant volcanic island, and visited the nearby hot springs.

If you’re visiting, skip the donkey rides in Oia. It was hard to watch how they were treated—and honestly, walking is the better experience anyway.

Santorini is undeniably beautiful, but I’d recommend 2–3 days max and balancing it with a less tourist-heavy island.

Folegandros: Peace, Sleep & Snorkeling Dreams

Folegandros gave me what I didn’t know I needed: stillness. It’s quiet, lowkey, and stunning in that effortless, “don’t need to try too hard” kind of way.

We explored Chora, the island’s sleepy main town, and hiked to the Church of Panagia at the very top of a hill. The view from up there? Breathtaking. You can literally see the whole island from that one spot.

The beaches here were crystal clear, and the water shimmered in shades of turquoise and aqua. I really wanted to go snorkeling—it would’ve been the perfect spot—but Madeline doesn’t swim, and I wasn’t about to go alone.

If you’re into cats, quiet nights, and minimal crowds, Folegandros might be your favorite too. It was the perfect contrast to all the energy in Mykonos and Santorini. Just know: two days is plenty.

Athens: Layers, Graffiti & the Unexpected

We saved Athens for the end of our trip—and after all the island hopping, we were exhausted but curious. The city surprised me. It felt like New York with way more graffiti and some serious wear and tear. Not what I expected, but definitely memorable.

We hit the classics: the Acropolis, Parthenon, and Ancient Agora—all stunning, especially at night when the ruins glow over the city. The Acropolis Museum was a standout too, built above ancient ruins you can see through glass floors.

But Athens is layered. One minute you’re admiring history, the next you’re dodging street scams or passing graffiti-covered buildings. It’s raw, real, and a little overwhelming. Still, places like Plaka, the old historical district, gave the city charm and balance.

You only need 2–3 days here to take it all in. It’s not just about what you see—it’s what it makes you feel.

What I Learned

Every place we visited had something to teach:

• Mykonos reminded me to have fun and not take myself too seriously (even when caught off guard at a nudist beach).

• Naxos reminded me that kindness is the best kind of luxury.

• Santorini showed me that beauty can be skin deep—but the sunsets are still worth showing up for.

• Folegandros taught me to slow down, get quiet, and rest.

• Athens reminded me that travel isn’t always pretty—and that history, grit, and reality often exist side by side.

And most importantly, I learned that the right travel partner can make anything—chaos, catcalls, ferry delays—feel like part of the adventure. Traveling through Greece with Madeline was a trip I’ll never forget.

Planning Your Own Greece Adventure?

If you’re ready to start dreaming (or booking), I’ve got you.

My Greece Island Hopping itinerary is now available as a digital download—the same route Madeline and I took, all mapped out to help you plan with ease.

• Includes transportation tips, island highlights, food and activity recs, and more.
• Perfect for best friend getaways, first-timers, or anyone who’s tired of overplanning.

And if you ever want to hop across Greece with me in real time… stay tuned. The Travel Invite just might make it happen.