Island Hopping in the Cyclades: Discovering Naxos & Santorini

Hannah Truman
Sep 7, 2021
5 min read

Updated: Jun 11

The most famous group of islands in the Aegean Sea, the Cyclades Islands in Greece is the ideal summer destination. The distinctive architecture of the white and blue houses overlooking the crystal blue water is iconic on Instagram and I finally had the opportunity to see it in real life. It definitely lived up to the hype!

Keep reading to see why Greece should be added to your travel bucket list!

Out of all the islands we visited, Naxos was my husband's favorite and it is easy to see why. As the largest and greenest of the Cyclades, Naxos feels like a breath of fresh air with dramatic mountain landscapes, fertile valleys, charming whitewashed villages, and some of the most beautiful beaches in Greece. It offers the perfect blend of nature, history, and authenticity without the overwhelming crowds of its more famous neighbors.

According to Greek mythology, the island was blessed by Dionysus, the god of wine, who filled the land with vineyards and lush greenery. That mythical fertility lives on in Naxos’ thriving agricultural scene, delicious local products, and a slower, more grounded pace of life.

Whether you are hiking through its scenic interior, wandering ancient ruins, or relaxing on the beach, Naxos invites you to slow down and truly enjoy the magic of the Greek islands.

Hike up Mt. Zas - the tallest mountain of the Cyclades

Mt. Zas stands as the highest peak in the Cyclades at 3290 feet, and it holds a legendary place in Greek mythology. It is said to be the birthplace and childhood home of Zeus, the king of the gods. Along the way, you can even explore the cave where Zeus is believed to have been raised.

The hike offers a completely different landscape from what we are used to as Mainers. Instead of dense forests, you will find rocky trails, low shrubbery, and wide open views that stretch across the island and out to the sea. The climb is a bit challenging in parts but well worth it for the sweeping vistas and the sense of mythic history all around you.

Tip: There are two ways up the mountain. You can begin at Filoti or Agia Marina. If you want an easier (less steep) way up, the public bus has a stop at Agia Marina, the next stop after the village of Filioti. For a more challenging hike, opt to start at Filoti instead.

We went up the easy way and came back down the steep trail so that we could see the cave and catch the bus at Filoti.

Explore Naxos Town (Chora)

Chora is the main town of Naxos and is the port to where most visitors enter. To the left of the port, a paved road leads to an unfinished Temple of Apollo and the famous emblem of the island, the Portara (meaning Big Door) which is the gate of the temple.

Naxos Town is built with both Venetian and Cycladic elements and even has a Venetian castle sitting at the top of its hill.

Enjoy the Naxos beaches

Naxos is known for its long stretches of soft sand and calm, crystal-clear waters—and Agios Prokopis Beach is one of the best. Our hotel was just a short walk away, making it an easy and relaxing spot to spend the day. The beach is lined with sunbeds and umbrellas, perfect for settling in and soaking up the sun, and the water is warm, shallow, and perfect for swimming.

Right behind the beach, you will find a great selection of beachfront cafes and restaurants. One of our favorite meals of the entire trip was at a casual spot called Kavourakia, just across from the bus stop. Their gyros were out of this world—I will be dreaming about that gyro for a long time!

Whether you are lounging by the water, grabbing a bite to eat, or taking a sunset stroll, the beaches of Naxos offer the kind of laid-back beauty that makes you never want to leave.

Santorini is a popular vacation spot and now I see why! The island is just as stunning in person as it looks in pictures. It was formed by a huge volcanic eruption back in the 17th century BC, which created the unique shape of the beautiful caldera. The cliffs rise sharply from the deep blue sea, and the villages like Oia, Fira, and Imerovigli seem to hang right on the edge.

The whitewashed houses and bright blue domes make for some seriously amazing views around every corner. Watching the sunset over the Aegean Sea from the caldera is something you won’t forget anytime soon. Beyond the views, Santorini has so much to offer: ancient ruins, colorful beaches, and fresh seafood that tastes just as good as it looks.

Whether you’re exploring the volcanic history, relaxing by the water, or just wandering through the charming villages, Santorini is a place that stays with you long after you leave.

Walk the 6-mile trail from the town of Fira to Oia

If you want to explore Santorini beyond the towns themselves, this 6 mile hike from Fira, the island’s capital, to the beautiful village of Oia is a must. The trail takes about three hours and offers some of the most stunning views of the island’s unique landscape. What I loved most about this hike was how the path winds right along the edge of the cliffs, giving you incredible views of the caldera and the Aegean Sea the whole way. It quickly became one of my favorite things to do on Santorini.

Tip: We had our hotel shuttle drop us off in Fira so we could hike back to Oia. You can do the trail either way, but starting in Fira means most of the walk is downhill (though there are still some hills to climb!). Plus, you get the amazing views of Oia ahead of you as you go. It’s best to do this hike early in the morning or later in the afternoon to avoid the strong midday sun.

Swim in Ammoudi Bay

Just below the town of Oia, Ammoudi Bay is the perfect place to swim, enjoy a seafood dinner right by the water, and even try cliff diving if you are feeling adventurous. I took the plunge myself. It was both refreshing and thrilling (check out the picture below of me in mid air!) It is a great spot to cool off and take in the stunning views of the sea.

The views from the bay are just as spectacular as they are from above, however, be prepared to wind your way down 300 steps or so. On your return, you have the choice to pay for a donkey ride to take you back up!

When you get to the bottom, you will have to walk straight through the Ammoudi Fish Tavern restaurant on the left, which is known for having excellent fresh seafood. Follow the path around the cliff edge to the accessible part of the bay to get into the water.

Tip: Bring comfortable shoes (enclosed, if possible)! You have to climb over rocks and it can be dangerous and extremely uncomfortable for your feet on the jagged lava rocks.

Stay at a resort in Oia and take advantage of the incredible views

We stayed at La Perla Villa & Suites in Oia, Santorini and it was the highlight of our vacation! The property has an infinity pool with sunbeds and looks over the Caldera. Our cave house-style room had our own private jacuzzi and breathtaking view.

In addition to the beautiful property, we were impressed with the service. La Perla's website boasts "top-of-the-notch service" and I would 100% agree! The bellboy carries your luggage up and down the steep steps quickly with ease. The hotel concierge will book any reservations, shuttles, or answer your questions 24/7. A breakfast fit for royalty will be served on your balcony. This hotel is definitely worth the splurge!