Island Hopping: An Unforgettable Greek Getaway

There’s something magical about exploring the Greek Islands and doing it with my daughter last October, made it even more unforgettable. We set off on a journey that took us from the vibrant heart of Athens to the tranquil charm of Koufonisia, soaking in sunsets, history, and plenty of delicious food along the way.

October turned out to be a great time to visit, with quieter crowds, cooler temperatures, and the same jaw dropping beauty at every turn. Worth noting, though, that by this time of year, many businesses are starting to close for the winter, so not everything will be open. If you’re looking for more choice when it comes to restaurants, shops, and activities, while still avoiding peak-season crowds, I’d recommend going in early to mid-September.

Thanks to Greece’s well connected ferry network, each island felt easily accessible, making it simple to hop from one destination to the next. Just be sure to book your ferry tickets in advance, especially during peak travel months, to secure your preferred times and routes.

We spent around two days on each island, just enough to fall in love but not quite enough to see it all. If you’re planning your own adventure, consider giving yourself an extra day or two. Trust me, you’ll want it and like much of Greece, cats are everywhere, lounging in sun drenched doorways, weaving through tavernas and restaurants, adding to the island’s laid-back personality.

Athens: Where Myth Meets Modern Magic

We started our adventure off in Athens, a city buzzing with energy and rich in ancient tales and mythology. Watching the sunset over the Acropolis from a rooftop bar felt surreal, like the perfect introduction to Greece. We wandered through ancient ruins, marvelled at stories of Greek gods and goddesses at the Acropolis Museum, and got a true taste of local culture with flaky custard filled bougatsa and mouthwatering gyros in the bustling streets of Plaka.
And for fellow coffee lovers, don’t miss the Freddo Cappuccino, Greece’s signature iced coffee. Strong, smooth, and frothy, it became our go to drink every day.

Milos: Raw Beauty and Cliffside Charm

Next stop was Milos, a volcanic gem known for its lunar like landscapes. With a rental car and no agenda, we cruised through charming villages and along narrow coastal roads. Highlights included the colourful fishing village of Klima, the striking white cliffs of Sarakiniko Beach, and a sunset dinner at the famous Medusa restaurant at Mandrakia, right by the water. The traditional Oi Hamos Tavern, with its farm to table flavours, was a culinary highlight.

Mykonos: Iconic Sights and Seaside Vibes

Mykonos surprised us. It’s known for its glitz and glamour, but in October it feels more laid back and inviting. We explored the famous windmills overlooking the sea and wandered through Little Venice, where waterfront bars spill out over the edge of the Aegean. We indulged in a little boutique shopping, sampled pastries from the local bakery, and feasted on some of the freshest seafood we’ve ever had.

Paros: Village Vibes and Waterfront Dining

Paros was a dream, especially the hilltop village of Lefkes with its cobbled lanes and timeless charm. Parikia offered the perfect mix of history and harborside relaxation, while Naoussa stole our hearts with its vibrant waterfront dining scene. The food was fresh, flavourful, and full of heart.

Naxos: Easy going Island Life

Naxos offered the most relaxed vibe of all the islands. We spent our time wandering golden beaches, eating long lunches, and soaking in the unpretentious charm. It’s the kind of place where time slows down and you’re grateful for it.

Koufonisia: Small Island, Big Soul

Tiny but mighty, Koufonisia is a place you can walk across in an afternoon. Though many spots were winding down for the season, we still found quaint shops, family run tavernas, and some of the most crystal clear blue water we have ever seen. One of the most memorable moments came from our lovely villa host, who didn’t speak any English, but thank goodness for Google Translator, which really helped to communicate without too much confusion. She kindly prepared us a traditional Greek breakfast each morning. It was simple, fresh, and delicious, a perfect example of Greek hospitality at its finest.
Its simplicity and natural beauty made Koufonisia truly special.

Santorini: Sailing, Wine, and Jaw-Dropping Views

No Greek Island trip is complete without Santorini. We explored the iconic white and blue villages and couldn’t stop taking photos of the breathtaking cliffside views. Our sunset Oia Santorini Gems cruise around the caldera was hands down one of the highlights of the trip. Sailing past volcanic rock formations and diving into warm turquoise waters felt like a dream. We also enjoyed a local winery tour, learning about Santorini’s unique volcanic soil and tasting some incredible wines with unforgettable views.

Crete: A Taste of the Largest Greek Island

Our final stop was Heraklion in Crete. While we only had time to explore the main harbor area, we could sense that there’s so much more to discover on this island, which is the largest in Greece. From ancient Minoan history to dramatic mountain landscapes and charming coastal towns, Crete is firmly on our list for a return visit with more time to explore.

Why Greece?

Because it’s a place where every island has its own personality, where the food is unforgettable, the people are warm and welcoming, and the pace of life invites you to slow down and savour every moment. From ancient Athens to the sun-soaked islands of the Aegean, this journey left a lasting impression on us both.

I can’t wait to return and discover even more of what Greece has to offer.