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 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 yacht vacations in Greecebased on Paros island in the very center of the Archipel of the Cyclades.

Cyclades islands

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

If you are searching for a sailing vacation for couples or you are 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.

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.

prices 2021 for a Greek Isles sailing vacation- Cyclades --5 days starting from 2090€ (boat+skipper)--7 days starting from 2700€ (boat + skipper)

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

Our crew

Sailing the Cyclades

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 mythology – Poseidon, 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 natural beauty to compete any of the world’s dreamy island escapes.

What to expect:

plenty of islands and places to visit

inter island short sails

protected waters

unique nature and beauty of the landscape

perfect climate

adventure vacation in cosmopolitan places or isolated ones

costs no more than a holiday in a hotel room because of saving money for your accommodation, meals, and tickets. Cheap sailing with skipper Greece Cyclades

swimming off the back of your yacht in warm, clear waters.

always a waterfront table or magnificent view, no tourist crowds or queues.

spend evenings ashore and enjoy the best tavernas, restaurants, and cafes.

visit beautiful natural bays only accessible on a yacht for lunch, swimming, snorkeling & relaxing.

no fixed itineraries – you decide the pace, where to go and when

fun, romantic or relaxing escape

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 in 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 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.

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:

Short Sailing Holidays in Greece

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:

 catamaranmonohull)for Greek sailing excursions. 

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.

Beneteau 40

2 -4 guests

7 day and short sailing trips

Lagoon 39 Catamaran

up to 8 guests

7-day sailing trips


up to 8 guests

7-day sailing trip

Greek islands yacht holidays prices 2022

Prices are for the Beneteau40
Prices in €/week for skippered charter October May, June & September July & August
For 2 people 2700 3250 3550
For 3- 4 people 3100 3550 3850

What package includes: VAT 24%, the sailing yacht with all her equipment, skipper’s fee, taxes, insurance, credit card commission

What is not included: drinks, the diesel(depends on the consumption), the marina’s fees at the islands that you are going to visit and the end cleaning.This amount is 260€ in total.

Sailing the Greek islands reviews.

“Perfection!!! 5 stars”

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. Michael

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Apostolos V

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