There’s a moment that happens on almost every Cyclades sailing holiday. The engine goes quiet. The sails fill. The water turns that impossible shade of blue. And suddenly, Greece feels exactly the way you imagined it would.
The Cyclades Islands are iconic for a reason—but when you experience them by yacht, they become personal. You wake up anchored in a quiet bay before the ferries arrive. You swim straight from your boat. You choose when to explore, when to move on, and when to stay just one more night.
We help you experience the Cyclades the way they’re meant to be seen: by sea, at your pace, and with the right yacht for you. Choose a sailing yacht, catamaran, or motor yacht, departing from Athens, Lavrion, Paros, or Mykonos—with bareboat, skippered, or fully crewed options to match your comfort level.
Sailing in the Cyclades is exciting, beautiful, and full of character. This is where whitewashed villages meet dramatic coastlines, where steady winds create real sailing days, and where no two islands ever feel the same.
What our guests love most about the Cyclades:
Classic Greek island scenery
Clear water and unforgettable anchorages
A mix of lively ports and peaceful bays
Islands close enough to explore comfortably by yacht
The famous Meltemi wind adds energy to the experience. For confident sailors, it’s a thrill. For everyone else, a skippered, fully crewed, or catamaran charter keeps things smooth and enjoyable.
The Cyclades are located in the central Aegean Sea, southeast of mainland Greece. They form one of the most diverse sailing regions in the Mediterranean, with islands ranging from glamorous to wonderfully understated.
Some of the most popular islands for sailing itineraries include:
Mykonos
Paros
Naxos
Milos
Santorini
Syros
Serifos
Sifnos
Koufonisia
Each island adds its own flavor to your journey—and sailing lets you experience more than one without ever unpacking twice.
Athens is Greece’s largest yacht charter hub and a natural starting point for Cyclades sailing. With multiple marinas, excellent provisioning, and easy international access, it offers unmatched flexibility.
From Athens, itineraries can head west toward the calmer Cyclades or southeast for longer, more adventurous routes. This base is ideal for experienced bareboat sailors, as well as guests choosing skippered or fully crewed charters with maximum yacht availability.
Lavrion is one of our favorite “smart starts.” Located closer to the Cyclades than central Athens, it shortens the first sailing day and gets you into island waters faster.
Lavrion is especially popular with sailors who want more time sailing and less time motoring. It’s a great base for sailing yacht charters and confident bareboat crews, offering efficiency, simplicity, and excellent access to the islands.
Paros sits right in the heart of the Cyclades—and it feels like it. Starting your charter here means short hops in every direction and a relaxed rhythm from day one.
Paros is a fantastic base for catamaran and skippered charters. It combines charming ports, beautiful beaches, and welcoming villages, making it ideal for families, couples, and mixed-experience groups.
Mykonos is bold, stylish, and unmistakably Cycladic. Beginning your sailing holiday here puts you right in the center of the action.
This base is particularly suited to luxury motor yacht and fully crewed charters, offering high-end marinas, premium services, and easy access to iconic destinations like Paros, Naxos, and Delos. Perfect if you want comfort, speed, and standout experiences.
Famous for its beaches and nightlife, Mykonos is energetic and glamorous. Arriving by yacht lets you enjoy its highlights while retreating to quieter bays when you want space.
Paros is warm, welcoming, and wonderfully balanced. Great food, traditional villages, and easy anchorages make it a favorite stop for many of our guests.
Naxos is larger and more diverse, with long sandy beaches, fertile landscapes, and a laid-back atmosphere. It’s ideal for travelers who enjoy authenticity alongside comfort.
Milos is a highlight for many sailors. Its volcanic coastline creates colorful cliffs, sea caves, and some of the best swimming spots in the Cyclades.
Sailing into Santorini is unforgettable. Towering caldera cliffs and dramatic views make it one of the most striking arrivals in Greece—a must-see on longer itineraries.
A sailing yacht offers a classic, hands-on experience. It’s perfect for guests who love feeling the wind and being part of the journey.
A catamaran provides space, stability, and comfort—especially appreciated in the Cyclades’ stronger winds. It’s an excellent choice for families and groups.
A motor yacht delivers speed and luxury. You’ll cover more distance effortlessly, enjoy premium amenities, and experience the islands with total ease.
We’ll help you choose the yacht that fits your group, experience level, and travel style.
A bareboat charter is complete independence. You’re the skipper, the planner, and the decision-maker. Best suited to experienced sailors, especially during peak summer winds.
A skippered charter offers the perfect balance. Your professional skipper handles navigation and weather decisions while you relax and enjoy the ride.
A fully crewed charter is effortless luxury. With a professional crew on board, everything is taken care of—from sailing to meals—so you can simply enjoy the Cyclades.
May–June: Ideal balance of weather, wind, and fewer crowds
July–August: Peak season with lively energy and stronger winds
September: Warm seas, softer conditions, relaxed atmosphere
We’ll help you choose the best timing based on your sailing experience and expectations.
Sailing the Cyclades Islands is about freedom, beauty, and unforgettable moments at sea. With the right yacht, the right route, and the right support, it becomes the kind of holiday you’ll talk about for years.
We don’t just rent yachts—we help you sail Greece with confidence. From choosing the perfect sailing yacht, catamaran, or motor yacht to deciding between bareboat, skippered, or fully crewed,
📩 Ready to plan your Cyclades sailing holiday?
Get in touch with us today, and let’s design a yacht charter that fits you perfectly.
SEVEN – Sailing & Tourism Services is authorised by:
Ministry of Culture and Tourism
Greek National Tourism Organization
License No : 0458E60000094101
Member of HYBA:
