Sail the Cyclades – Join the Crew with sailwithus

Learn more about sailing holidays in the Cyclades

Arrival and departure

You want to sail in the Mediterranean and discover the Cyclades islands with an experienced skipper by your side: for this Cyclades sailing trip, you’ll first fly to Athens. You can get cheap flights if you book quickly, potentially saving many euros on your trip. Feel free to arrive a day earlier to explore the beautiful city of Athens.
From Athens Airport, you’ll continue east to the harbor town of Lavrio (Lavrion). The marina—your harbor—can be easily reached from the airport by bus, and you’ll meet us at the marina between 2 and 4 p.m. A later arrival is also possible; you can coordinate with your fellow crew members via our WhatsApp group, which will be created a few days before your trip. You’ll also receive detailed harbor information before your sailing tour begins.
We wish you a wonderful journey into the legendary island world of the Cyclades! On Friday, between 3 and 6 p.m., your yacht will return to the marina at Lavrio. It’s best to plan your departure from Athens Airport for the next day. At 9:00 a.m. on Saturday, you’ll leave the yacht and exchange contact details with your new friends.

The Gateway to the Cyclades

The small Cyclades island of Kea, with its white windmills, is affectionately called the “Gateway to the Cyclades.” It is the northernmost Cyclades island, still close to the mainland. Interestingly, the island is used by locals themselves as a holiday paradise—and for good reason. Here, you can snorkel in crystal-clear waters, relax on beautiful white beaches and picturesque bays, or take a day trip to the “Lion of Kea.” The large statue is visible from afar. According to legend, beautiful nymphs once lived on Kea but were driven away by a lion sent by the gods.

Kythnos, Loutra, and then Mykonos

On most crewed sailing trips in the Cyclades, the journey typically starts with the islands of Kea, Kythnos, Loutra, and then Mykonos. Like pearls strung together, these islands and their small harbors lie close to each other. The first two mountainous Cyclades islands are just a stone’s throw from Athens.
The anchorages here are peaceful, with hardly any tourists—perfect for leaving everyday life behind in a traditional local taverna onshore, or relaxing with your crew on the beautiful beaches and bays. This laid-back lifestyle is ideal for your first days on a Cyclades sailing holiday, before heading to the lively island of Mykonos.

Ermoupoli, the “City of Hermes”

Ermoupoli, the administrative capital of the southern Aegean, forms the heart of the Cyclades. The harbor town is located on the island of Syros, which means “rocky.” Ermoupoli is named after the Greek god Hermes, the protector of merchants and thieves, and translates to “City of Hermes.” Like many other towns on the island, it is built on its own hill.
What makes Ermoupoli special is its vibrant and colorful character. Take your time to stroll through the cobblestone streets and admire the mansions, neoclassical domed buildings, and the magnificent town hall. Ermoupoli also houses one of the oldest archaeological museums in Greece and the Apollo Theatre, built in 1861. Enjoy the view over two cathedrals toward the Mediterranean Sea!

Naxos – the largest island of the Cyclades

Naxos is often called the jewel of the Cyclades. With its traditional villages, long white sandy beaches, and the Chora—the island’s largest town, also known as “Naxos City”—it lives up to that reputation. On Naxos, you can easily reach the most beautiful sights on foot.
Our recommendation: cross the causeway to the Platia peninsula to visit the Portara. It’s best to go in the evening to enjoy the sunset from the gateway of the ancient Temple of Apollo. Then stroll along the wide waterfront promenade, stretching from Palatia to the town hall. When you’re in the harbor bay near the old town, make a detour to the Bourgos district. Head straight for “Old Market” street! The lively bustle in the shops and market stalls is incomparable.

Diverse nature on the Cyclades islands

The Cyclades islands will continually surprise you. One moment you’re in a lively small island town, and the next you find yourself immersed in the almost deserted seclusion of a bay on another Cyclades island. Folegandros definitely belongs to the wild, rugged beauties of the Mediterranean. Quiet and nearly untouched, it lies in the Aegean and was considered an absolute insider tip until a few years ago. Once used by the Romans as a place of exile, Folegandros is now, thanks to its seclusion, the ideal spot to unwind and relax. The spectacular cliff-top views over the Aegean are a must-have for Instagram.

When the honey raki flows. . .

On every island in the Cyclades during your sailing holiday, you’ll have plenty of opportunities to chat with locals in traditional fish tavernas. After the siesta, the tables gradually fill up, music plays, people sing, and often dance. Friendships are quickly formed—this is typical Greek hospitality! This is Greek mentality!
Especially delicious is honey raki—raki with honey. This rare specialty is produced, for example, in the mountain village of Temenia. The widely popular Temenia lemonade, made from spring water and common in many parts of Crete, was also invented here. It tastes somewhat like bitter lemon, and its secret recipe has been closely guarded since the 1950s by the family company in Temenia (George Garofalakis).

The volcano of Santorini

Undisputedly, Koloumbos is the main attraction of the island. The underground, active volcano lies in the northeast of Santorini. The town of Thira sits on the crater’s edge and can be reached by stairs or a cable car. From up here, you have a spectacular view, which is why Thira’s harbor is a popular anchorage for cruise ships.
As for its history: in 1650, a major volcanic eruption formed a small island from lava. Today, it rises 280 meters above sea level and lies about 18 meters below the surface. Around the volcano, hot springs have formed, and over time, a rare ecosystem has developed.

Where pine trees and citrus fruits grow

What unites all the Cyclades islands is their low tourism and plenty of quiet spots set against a true postcard panorama. As far as the eye can see, you’ll spot the typical white-and-blue houses, flowers and grapevines, the emerald-green sea, and rugged mountain landscapes.
Green Paros, located at the heart of this island world, breaks all the Cyclades stereotypes. Here in the Saronic Gulf, fragrant pine trees and citrus fruits like lemons, mandarins, oranges, and pomegranates grow. We say: it’s perfect for a walk! The lemon grove (Greek “Lemonodasos”) points to a long trading history. The lemon forest of Paros was already mentioned in the 18th century by lemon traders in Galatas.

Venus and Milos

On your Cyclades sailing trip, you might not meet the Venus de Milo in person, but you can follow the footsteps of its famous history: the marble for this divine statue (2nd century BC) comes from the quarries of Paros, while the sculpture itself was a chance find in 1820 on the Cyclades island of Milos. Today, the Venus de Milo (Aphrodite of Melos) stands in the Louvre Museum and is considered an outstanding example of Hellenistic art.
It’s definitely worth taking a closer look at the bright “moon landscape” of Milos. The island in the southern Aegean is better known as the “Island of Colors.” Its landscape resembles a painting: red volcanic beaches meet white tuff stones in Sarakino, sulfur-yellow cliffs in Paleochori contrast with the shining emerald of the sea.

Greek Food & Greek Wine

A visit to a traditional fisherman’s taverna or a small harbor restaurant begins with appetizers and ends with a complimentary glass of ouzo. Besides tzatziki, saganaki, or gyros, you absolutely must try a classic from Crete: dakos. This simple dish requires just a few ingredients, including dark, long-lasting paximadi bread (Greek rusk), tomatoes, and feta cheese—essentially the Greek answer to Italian bruschetta.
Afterward, try tsigariasto, a slow-cooked oven dish made from lamb or goat, simmered for hours to enhance digestibility. Pair it with a wine from Samos, Lemnos, Santorini, or Paros, the regions famous for Greece’s most renowned wine varieties.

Relaxation in the Loutra Hot Springs

On your Cyclades sailing holiday, you can combine your thirst for adventure with relaxation in a healing place. Both are possible in Loutra Pozar. And the best part is: the Loutra Pozar springs are among the most beautiful in Greece.
These hot thermal springs have been known since ancient times and still impress with their untouched, natural charm. The warm springs are nestled in pools amidst a mountainous landscape with waterfalls and caves. From here, numerous hiking trails lead into the surrounding nature, which is especially stunning in spring with its blossoming cherry trees. Alternatively, you can try one of the wellness treatments offered at the “bathhouse.”