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greek islands sailing trips

Private sailing trips in Greece

sailing vacations for couples

for couples

well maintained cruising yachts

for families

secluded coves

for friends

simplicity and authenticity

experienced skippers

from windmills to lighthouses

turquoise waters

for a group of friends

culture and history

picturesque villages

Greek Water Yachts

authentic - unique - intimate - memorable - safe

Sailing trip Greece / Sailing the Greek Islands

Sailing yacht rental Greece - Cyclades - Paros


Greek Island Sailing Cruises

Start your Greek Island cruise with a private skippered sailboat charter from the center of the Cyclades islands in the Aegean sea and set sail around the Greek Islands.

Your days will be washed by sun, bathing, sailing, good food and adventure.

Greek Water Yachts, an eco-friendly sailboat rental company, arrange crewed (skippered – captain) private charter sailboats for your vacations in Greecebased on Paros island in the very center of the Archipel of the Cyclades.

skippers of GWY

About us

We offer 7 days sailing trips in the Greek islands, but also short sailing holidays (5 days, 4 days, 1 day Paros cruise) according to the availability and the dates you are interested.

Our small fleet of modern yachts can accommodate 2,3 or 4 guests, are maintained to the highest standards of safety and comfort, and staffed by an exceptional crew (captain – sailor) with many years of local knowledge and experience.

Our private yacht tours from Paros island, are designed to avoid long, exhausting sailing legs and exposure to inclement weather – ideal for the experienced sailor and beginner alike.

If you are a group of 5, 6 or more persons looking for skippered Catamaran charter in Greece, or skippered sailboat cruise in Greece, we can also arrange this jaunt for you from our associates.

Ask for prices and availability

prices 2019 for a Greek Isles sailing vacation- Cyclades

5 days starting from 2090€ (boat+skipper)

7 days starting from 2700€ (boat + skipper)

Check out our last minute offers

Let Greek Water Yachts take you on an unforgettable sailing trip in Greece.


Sailing the Cyclades
Pick you group
Pick you sailboat
Pick you trip
Cyclades island group in a map of Greece. Your sailing tour area. Sailing the Cyclades

Cyclades island group in a map of Greece. Your sailing trip area. Click for details(opens in new window)

The Greek islands are grouped into the following clusters: the Argo-Saronic Islands; the Dodecanese; the North Aegean islands; the Sporades and the famous Cyclades-Kikládhes-, a large but dense collection of islands and islets occupying the central part of the Aegean Sea.

The beautiful Cyclades islands form a circle around the sacred island of Delos where – according to Greek mythologyPoseidon, God of the sea, furious at the Cyclades nymphs turned them into islands!

The Cyclades island group is a perfect choice for your inter-island private expedition with a skippered sailboat charter in Greece because it is an astounding combination of lifestyle, culture, history, cuisine, and a natural beauty to compete any of the world’s dreamy island escapes.




What to expect:

That’s why Cyclades Isles are the synonym of Greek Summer Vacation and one of the best places for a private voyage with a sailboat in the world.

That’s why Cyclades is an area that you must explore with crewed sailboat charter.

That’s why renting a sailboat with skipper from the Isle of Paros is the ideal starting point for your private yacht cruise through the Greek islands.

That’s why a skippered sailing trip is the best way to visit Greek islands


Pick your group

A Greek island boat tour with a captain is for everyone.

Find your profile below and learn more about your vacation options or even propose a new one.

Pick your skippered sailboat

Either you are searching for a private sailboat to charter in Greece or a Greek island catamaran cruise, Greek Water Yachts(GWY) can cover both of your wishes:

In our fleet, you can find the following vessels always with a captain as your guide:

  • 2 Beneteau’s Oceanis 40 sailboats with a captain that can accommodate 2 – 4 persons, 
  • 1 Lagoon 39 catamaran with a captain that can accommodate up to 8 persons from our associates:
  • 1 Beneteau50 with a captain that can accommodate up to 8 persons from our associates.

All the boats are operated many years only with a permanent captain and the careful maintenance at our base after each tour, provides to guests a guarantee of a safe trip,  a highlight of the quality of our work.

Pick your sailing trip/tour

There are 220 Cyclades islands, small or big ones. That’s why Cyclades islands are the main sailing destination area when we are talking about yacht charter sailing vacations in Greece.

Chartering a private yacht just for yourselves, you can customize your itinerary according to your tastes. Your skipper will be happy to guide you to the finest secluded coves, charming tiny harbors or more crowded islands. Experience secluded pearls, crystal clear waters and warm evenings.

Some of our boats are available only for 7 days Greek island sailing trips and some others also for short sailing holidays(5 days, 4 days or 1-day private sailing cruise from Paros – the Cyclades – Greece)

Starting from Paros we suggest the following sailing routes:

Sailing the Greek islands reviews

sailing the greek isles reviews


Our sail through the Cyclades with Greek Water Yachts was perfection from beginning to end and I cannot recommend them highly enough. A few reasons why:

– throughout the planning process, Apostolos promptly answered all of my emails and my many questions so I felt at ease navigating a new adventure.
– our captain, Antonios, put us at ease from the first moment we stepped on the boat and became a good friend and expert guide for our week-long sail.
– the boat was in wonderful condition and exactly as expected.
– we charted our itinerary with the captain, ensuring we felt in control at all times. He expertly explained the pros and cons of suggested routes and then left the decision to us.
– Antonios knows all the special, local places to go and instinctively knew what we’d like, how much privacy we needed, and how to ensure our trip fit our needs.

I can’t say enough good things about the Greek Water Yachts experience.


Click for more Greek Water Yachts TripAdvisor Traveler Rating

Sailing trips through Greece with 42 reviews

If you decompose Greece, in the end, you will find yourself with an

olive tree,

a vineyard

and a boat,

which means: with those you can compose it again.

Odysseas Elytis

Contact and booking

Whether you own a cruising schedule during your previous Greek Islands sailing adventure or need recommendations for your first private sailing experience in Greece, send an inquiry on Greek Water Yachts to get customized choices, prices, plan and guidance for your slow travel voyage.

You will be better informed with the info you’ll get.

Greece Sailing Vacations


Greek Water Yachts