Weekly cruises

Weekly Sailing Cruises

around Cyclades

Cyclades Islands, Where Dreams Come True

Discover the magic of the Cyclades, a place where ancient sailing routes meet breathtaking landscapes and endless blue horizons. With our 51.2-foot sailing boat, we explore the open Aegean Sea, hopping from one island to the next. Each destination reveals something new—secluded beaches, charming villages, and local tavernas filled with authentic flavors. The comfort of our boat is always there, waiting for you at the port or anchored in a quiet bay, ready for relaxation, a peaceful night’s sleep, or a refreshing swim. Picture this: your own private adventure, where every island becomes your home and the journey is yours to create.

Discover the Cyclades with a Skippered Weekly Cruise

Set off on a memorable adventure across the stunning Cyclades islands aboard our sailing boat, Princess. Whether starting from Heraklion port in Crete or the iconic island of Santorini, each journey offers a week or more of unparalleled exploration, crystal-clear waters, and endless island charm.

Short Distances, Big Adventures

The Cyclades are known for their close proximity, making each trip smooth and enjoyable. With distances ranging from just 2 to 30 nautical miles, sailing times vary between 30 minutes and 4 hours — perfect for a blend of relaxing sails and thrilling island explorations.

Life Onboard: Comfort & Freedom

Your journey isn’t just about the destinations—it’s about the experience at sea. Aboard Princess, you'll enjoy the perfect balance of adventure and relaxation. Start your mornings with a dip in crystal-clear waters, spend afternoons lounging on deck or exploring hidden coves, and savor peaceful evenings under a sky full of stars. With a fully equipped sailing boat as your home, you have the freedom to embrace the rhythm of the Aegean at your own pace.

A Journey Tailored by Wind and Exploration

We let the winds and your sense of adventure guide us. Depending on weather conditions and preferences, we sail to some of the most enchanting islands in the Aegean. Below is an example of a possible sailing route — but the beauty of this journey is its flexibility. Whether you’re seeking lively destinations or secluded escapes, large islands or hidden gems, cosmopolitan vibes, or archaeological wonders, we design each route with your desires in mind.

Anafi: Spend a couple of days soaking in pristine beaches and untouched landscapes. Created by Apollo, the god of light, Anafi is a divine combination of striking cliffs and golden sand.
Astypalaia: The “butterfly” of the Aegean is a carousel of well protected bays with its capital being a home to one of the most unique Venetian castles. Moor at the lively port or anchor in secluded bays for peaceful nights under the stars.
Amorgos: Wander around the one of the most beautiful Choras of the Aegean. A town taken straight out of a Greek fairytale. Breathtaking monasteries hanging off the cliff and peculiar shipwrecks are just a few of the island’s mysteries.
Schinousa: Have you ever covered a whole island by foot? Schinousa is just 9 sq. km and you can easily walk around it in a couple of hours. With a relaxed, unhurried way of life, briefly stirred by lively festivals, this island is an ideal spot to unwind and enjoy tranquility.

Let Princess become your floating home, offering comfort and convenience as we move from island to island.

Why Choose Our Weekly Sailing Cruises?

Explore multiple islands effortlessly, free from ferry schedules.
Wake up each day to a new breathtaking destination in the comfort of your boat.
Experience a flexible journey tailored to the weather and your preferences.
Sail on a safe and comfortable boat, built in Greece and designed specifically for navigating in Aegean’s weather conditions.
Follow one of the most ancient sailing routes, steeped in history and maritime tradition.
Enjoy the perfect blend of adventure and relaxation, with opportunities to explore remote beaches, charming villages, and cultural landmarks. Let’s make your next adventure unforgettable — a journey where the Aegean Sea becomes your playground.