Island Hopping Through Greece: Our Highlights & Inspiration Behind the SS26 Collection

If you’re dreaming of visiting Greece in October, consider this your sign. We took a direct flight from JFK to Athens and spent the 10 days during the end of September and first week of October exploring the city and island-hopping through Milos and Paros. The weather was perfect, the crowds were minimal, and the experience shaped the inspiration behind our SS26 Greek Collection.

Athens: The Perfect Start to a Greece Trip

We arrived in Athens to ideal fall weather: warm sunshine, a light breeze, and comfortable walking temperatures. With only one day in the city, we headed straight to the Acropolis, which was surprisingly peaceful without the peak-season crowds.

Walking through the historic center felt like stepping back in time, and enjoying inexpensive (and delicious) Greek wine with views of ancient architecture set the tone for the rest of the trip.

How long to stay in Athens:
One full day is enough unless you want to explore museums or additional neighborhoods. The islands are where Greece truly shines.

Catching the Ferry to Milos: What to Expect

We woke up early the next morning to catch the Seajets Ferry to Milos. It was slightly bumpy — fast ferries usually are — but nothing unbearable. Once we arrived, we walked straight to Europcar where our rental was ready.

Important tip: Bring your passport and your driver’s license.
Our designated driver forgot hers (looking at you, Victoria), so someone else had to take the wheel.😅

Milos: A Laid-Back Greek Island With Heart and Soul

Milos instantly felt different from the busier islands — smaller, slower, deeply local. The main town is walkable, but exploring the island requires a car.

What We Loved in Milos

• Eating authentic gyros everywhere we went
• Returning multiple times to the famous Medusa Restaurant
• Interacting with warm, welcoming locals
• Experiencing breathtaking coves and clear water on a private boat tour

We booked a half-day private boat tour, which was more than enough to explore hidden beaches and swim in calm, turquoise water. October made everything better: fewer tourists, lower prices, and still warm enough for a dip.

And yes, it’s true what they say — Greek fries are unreal. Freshly cut, perfectly fried, and unforgettable. Same with the house wine — smooth, light, and seemingly endless.

Why Milos Stands Out

What made Milos magical wasn’t just the scenery.
It was the locals who invited us into their world — sharing hidden spots, late-night hangouts, and conversations that gave us a deeper appreciation for Greek culture. Their love for their island is contagious.

Next Stop: Paros — Stylish, Lively & Full of Options

From Milos, we took the ferry to Paros and then hopped on a bus just steps from the port.

Note: Pack light, or pre-book a car/taxi. Carrying heavy luggage uphill to your Airbnb will humble you (trust us).

We stayed in Naousa, just a five-minute walk from the main part of town. It’s full of beautiful boutique hotels and has a vibrant but relaxed atmosphere — especially in October.

How Paros Compares to Milos

• Milos → smaller, laid-back, raw beauty, more local
• Paros → more shops, more restaurants, more tourist-friendly
• Both are stunning; it depends on the vibe you want.

Highlights of Paros

• Plenty of restaurant options without the usual lines
• Warm afternoons with occasional light showers
• Renting a car for the last two days to explore more
• Visiting Antiparos, which was peacefully quiet as the season was ending

One charming detail we learned: at the end of the season, many locals close their businesses and head back to their hometowns for rest and family time. It’s a lifestyle that feels beautifully balanced.

Returning to Athens: Slow Ferry for the Win

We ended our island trip with the slow Blue Star ferry back to Athens. Because it was off-season, it wasn’t crowded at all, and we enjoyed the reserved seating section.

With a little extra time in Athens, we walked around the city one last time before heading home — and our hearts were full.

 

Would We Go Back to Greece? Absolutely — Again and Again

This trip was not only one of our favorites, but it also deeply inspired our upcoming SS26 Greek Collection. The beauty, soul, and history we experienced in Greece translated directly into the colors, textures, and mood of the new line.

We can’t wait to share it with you.
Stay tuned — it’s dropping very soon.

Xx, 
Carasoles