Call Us Today! +30 6932299490 & +30 6977206845|
Greek Islands Sailing Trips with skipper

Private sailing trips in Greece

Special offers on certain dates. Contact us for more info

Full refund due to Covid-19 restrictions

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

paros sailing trips

picturesque villages

beach stones in the Cyclades

Greek Water Yachts

authentic - unique - intimate - memorable - safe

Greece sailing tour / Sailing in Greek Islands

Sailing yacht rental Greece - Cyclades - Paros


Greek Island Sailing Cruises

Start your Greek Island sailing tour with a private skippered sailboat charter from the center of the Cyclades isles in the Aegean sea.

Private sail around the Greek Islands and your vacation days will be washed by the sun, amazing waters, sailing, good food, and adventure.

special last minutes offer for yacht charter in Greece

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

greek water yachts skippers

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

If you are searching for a sailing vacation for couples or you are a small group 3 or 4 persons, our small fleet of modern yachts can be a great choice. The boats 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.

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

A private Greek sailing experience from Greek Water Yachts, is designed to avoid long, exhausting sailing legs and exposure to inclement weather – ideal for the experienced sailor and beginner alike.

prices 2023 for a Greek Isles sail vacation- Cyclades

5 days starting from 2490€ (boat+skipper)

7 days starting from 3230€ (boat + skipper)

Check out our last minute offers

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

We expand to a new area:

Sailing the Ionian Islands 

Sail from Athens to explore the Saronic Islands

More flexibility in our cancellation deadlines and fees due to corona-virus



Cyclades island group in a map of Greece. Your sailing tour area. Sailing the Cyclades

Cyclades island group in a map of Greece. Your sail 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 isles, 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 island hopping with a skippered sailboat charter in Greece because it is an astounding combination of lifestyle, culture, history, cuisine, and natural beauty to compete any of the world’s dreamy island escapes.




What to expect during a Greek island charter cruise:

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 experience with skippered yacht hire greece.

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 tour is the top way to visit the Greek islands


Pick your group

A private sailing around Greek islands 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 Lagoon 39(4wc version) catamaran with a captain that can accommodate up to 8 persons from our associates:
  • 1 Sun Odyssey 440 sailboat with a captain that can accommodate up to 6 persons from our associates.
  • 1 Lagoon 42 a/c catamaran 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

Greece yacht vacations are your gateway to exploring the Cyclades, We’ll take you to the world’s outstanding cruising grounds of the Cyclades, south of Greece, which
are considered some of the most beautiful islands in the world. Mountains, white cubistic villages and black and golden sand beaches combine to make the islands picture postcard-perfect.

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

Chartering a small yacht in Greece for private sailing around the Greek islands, you can customize your itinerary according to your tastes. Your skipper will be happy to guide you around the finest secluded coves, charming tiny harbors, or more crowded islands. Visit pilgrimage sites, experience secluded pearls, crystal clear waters, and warm evenings.

Some of our boats are available only for 7 days private 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 cruises in the Greek Islands On Your Private Yacht

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 for Greek Water Yachts at Sailing Greek Islands Tripadvisor

Best Greek Island Sailing tours

Sailing greek islands reviews TripAdvisor

TripAdvisor Sailing Greece Charter

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 around the Greek Isles, send an inquiry on Greek Water Yachts to get customized choices, prices, plan and guidance for an Odyssey of your own.

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

Greece Sailing Vacations


Greek Water Yachts