Have you dreamed of traveling the Cyclades like an ancient Greek…exploring new lands by sea?

I know, Homer has a lot to answer for (thank you!!). The gentle wind in our hair, warm sun inviting us to sit and bask, mesmerizing waves, rocky islands that entice us to explore, stunning blue waters…well, the list goes on and on, and we can see why Odysseus took some time to get home.

Luckily, we can explore Greece’s many islands by sea, via private gulet charter that not only indulges our passion for great literature, but brings us right into the beauty, easy exploration, and relaxation of journeying here. 

Here are our four favorite Greek islands to explore via sea—and when and what to do while you’re cruising the Cyclades in the Aegean Sea. Let’s start with a gulet cruise Santorini:

Santorini

The furthest south on our Cyclades Island adventures, Santorini (known in antiquity as Thera) is a calderic island. This means you have plenty of steep cliffs…and incredible views. There are two main towns on Santorini: Oia and Fira. We recommend Oia, located at the top of the caldera, for the quintessential views of whitewashed buildings, windmills, blue domed churches, and, of course, the water. 

While Oia is famous for its sunsets, it is well worth rounding the tip of the caldera for a gorgeous sunrise to start your day, coffee in hand.

Here’s an ENTIRELY unique experience: After mooring, head to shore and arrange for a donkey ride from the harbor to the village of Oia. Don’t worry! These donkeys are used to carrying people up the hill, and also entertaining via their braying chatter. It’s a great way to move from sea to land. (Hot tip: if you want a smoother way to descend, take the cable car.) Once up top, visit some of those beautiful domed churches, explore the ruins of the 15th c Oia Castle, and meander through alleys, finding the perfect café (we recommend Skiza, for the delicious pizza, coffee options (or a milkshake, if you’re hot), and the views).

Tip: Because the streets and staircases are quite steep, wear comfortable, stable shoes.

Those famous Oia sunset views…the crowds of people that also love Santorini and want a sunset photo can be a lot to contend with. My suggestion? Head back down to your gulet for a peaceful, stunning sunset. You can relax with your favorite beverage, rocked by the gentle waves, and revel in the beauty.

If you’re into Greek mythology, as I am, a stop at any of the three black volcanic sand beaches (Perissa, Perivolos, and Kamari) will put you in mind of Hephaestus, with the reminder of the heat of the volcanoes that created the Cyclades, throughout antiquity.

Milos

Next, set sail for the island of Milos, one of the very first Greek isles to be inhabited, in the Neolithic era. Here, the pieces of the Venus de Milo were unearthed! Moor and then head onto the island to explore the many archaeological sites, including Klima, a millenia-old city, catacombs, the spot where the pieces of the Venus de Milo were unearthed in 1820, and an ancient Roman theater. Museums include the Archaeological Museum, the Folk Art and History Museum, the Mining Museum, and the Ecclesiastical Museum.

One of the best ways to explore some of Milos’ 76+ beaches is by boat, of course. Some of those beaches are white gold sand, others are pebbled. Some are quite trendy, while others feel remote and quiet. Drop anchor to beach hop those clear, enticing waters for a swim or short exploration. Be sure to stop on the north shore at Sarakiniko Beach, the most popular on the entire island. The rocks and geography are absolutely stunning—one end is lunar-esque, while the other is more desert-like. 

Of special note are the cheeses of Milos. You know me, all about the cheese. The volcanic landscape offers both grazing opportunities for goats and caves for curing these cheeses. Some are not offered anywhere but on island; ask your captain for their best recommendations. 

Photo: Visit Greece Facebook 

Paros

Paros offers a cornucopia of things to do. There are so many beaches to visit and enjoy (windsurfing is a popular activity here). 

Of note, the beach of Kaloyeros has quite a unique spa experience. Head to either end of the sandy beach to acquire clay from the rocks; mix with water and apply. Then sit and bask in the sun while the mud and seawater heal your skin. Note: watch the waves, as ships going by can cause a big splash.

Nature is a main character on this island. The national treasure, Paros Park, offers activities as well as an opportunity to explore nature. In the summer, there are free festivals, concerts, movies, theatre performances, and more. In addition to three beaches, there is a walking trail network that crosses the Ai Yannis Detis peninsula. Here, you can see geographical, historical, and architectural treasures, as well as extraordinary views of the Aegean and the Cyclades.

Be sure to make time for the Butterfly Nature Reserve, also called Petaloudes. While it is incredibly beautiful year-round, if you visit between June and September, you can see the spectacular Euplagia quadripunctaria moths enjoy this natural haven. You'll feel as if you are in a different world amidst the ancient trees, stone paths, and ruins.

In the town of Paroikia, history comes alive at the Byzantine Museum, the ca. 13th c Venetian Castle, and the Archaeological Museum, as well as a plethora of archaeological sites (including an archaic Temple of Athena, Hellenistic arts workshops, the sanctuary of Asclepius). Other museums on the island include the Folk Culture Museum of the Aegean Sea in Lefkes, and Skorpios, a Cyclades Folk Museum in Alyki.

Rineia

For a distinctive beach experience, ask your gulet captain to stop at the uninhabited island of Rineia, located next to the uninhabited sacred island of Delos (a UNESCO World Heritage Site, where there is an incredible archaeological museum). On Rineia, there have been many important archaeological excavations; you can explore the ruins. There are four main beaches on the island, and you can enjoy peace and quiet of those blue, blue waters at any of them; they are easily accessible by boat.

Wikimedia Commons: KATYFOUSKI

How to go

The best way to travel these Greek islands? By gulet! These sailing yachts offer a travel experience like no other. 

You will be able to have a portable home base, without hauling luggage, finding luggage storage (especially in hilly Oia), checking in and out of hotels, arranging transportation, and worrying about timelines other than your own. You’ll also have the best and freshest cuisine, made to order on your timeline (yes, as aforementioned, I’m one of those early morning sunrise breakfast people).

With the captain, you can choose your itinerary…and have knowledgeable gulet captain and staff that can take you to the best beaches available only by water, share their favorite local restaurants and shops, and help with any accessibility needs. 

If you’re also a water person, you’ll also appreciate the ample opportunities to get in the water, whether it is snorkeling, having fun with water sports, or swimming at the countless beaches in Greece’s Cyclades islands.

When to go

We almost always travel during the shoulder season, for a variety of reasons. 

First is the crowds – most people travel in the high (summer) season. This leads to hard-to-get reservations, long wait times at restaurants, increased high season prices, more expensive flights, etc. 

When exploring the Greek islands, you should be aware of the Meltemi (or Etesian) winds, which are strongest in the Aegean Basin from mid-May to mid-September. This can affect all aspects of your journey, so do your research when travel planning. If you’re a total weather geek, this site from the national meteorological agency is so fun to dig into, and can help with timing your journeys.

When you travel in the shoulder season, you often have great weather (not too hot, not too cold), a slower pace of life, more cultural festivals and events that cater to locals instead of tourists, and fewer crowds. It’s so much more relaxing and magical, and you can truly slow down and experience the best of the Cyclades…at your own pace.