Sailing in Greece’s Islands

Greece is among the best destinations for sailing! You should consider it for your next vacation! Whether someone wants to get away from his busy schedule or have some fun time with family or friends, sailing in Greece’s islands is a great option.

Some of the islands people can sail around and visit include Mykonos, Santorini, Ionian Islands, Cyclades Islands, Kalymnos, Ikaria, Astypalaia, Chalki, Kastellorizo, Kasos, Karpathos, Tilos, Symi, Patmos, Nisyros, and Leros. They enjoy the great weather Greek has to offer, its culture, and nature.

If tourists don’t have a lot of time for sailing in Greece islands but still want to enjoy seeing them and being in the crystal waters, they can do one day trips. They can enjoy the long history, relaxing atmosphere and see amazing mansions and architecture. There are also many vacation-worthy activities to participate in. The experiences and views are unforgettable, the people of Greece are also friendly, and tourists don’t have to worry about losing their belongings.

Season of sailing

The season for sailing in Greece starts from April to November, similar to other Mediterranean countries. However, the peak season starts from the last week of June till Mid-September. Those are the summer months when there is usually a lot of sun with temperatures between 26 and 30 degrees Celsius. The water temperatures are high, perfect for swimming and other water activities. During this time, however, there are usually a lot of people.

For people who want a more quiet and private time, sailing in April, May, and early June or September, October and November are perfect times. Sailing in Greece during spring allows people to enjoy the beautiful flowers and lush green hillsides, plus they can also go biking, hiking, or trekking. Autumn is also perfect for sailing in Greece islands because the water is still warm, and the heat has gone down.

There will also not be the Meltemi warm and dry winds that could cause seasickness. The days are, however, shorter, which could reduce the fun. Before choosing the destination to sail to, people need to research how long it takes and how many hours a day they need to sail.

Captain Yannis Sailing Trips is the best option for people who want to do a sailing trip in Greece. People can choose different destinations or even book a private cruise.

Private Cruise Sailing in Greece

Cruisers who want to go island sailing in Greece alone in the boat can book the Catamaran Filippos. They can celebrate their birthday with their friends, make a special wedding proposal to their loved one, who will hardly be able to refuse :), baby shower parties, anniversary trips,  or any other special occasions. The private cruise can start from many islands like Paros, Mykonos, Naxos, and Santorini. Unlike other cruises, private cruisers can choose the route and destination they want to go to.


The minimum rental period for the yacht for a private cruise is two days, and it comes with a professional and experienced skipper plus a hostess. Some suggested routes are Nature and Relax, Posh and culture, unique, west Cyclades 1, and west Cyclades 2. The charter rates are usually weekly, with the most expensive times being the summer season because it’s the peak sailing season in Greece. There are also additional charges for cleaning, skipper, and hostess. When booking the private cruise when sailing in Greece, cruisers need to fill in where they want to start, the route that suits them best, and how long the cruise will take.

Customers can also choose their own destinations, but these are some suggested sailing routes:

  • Nature and Relax
  • Posh and culture
  • Unique
  • West Cyclades 1 & 2

For more details, check out our “chartered private cruises” page.

One Day Island Sailing in Greece

Sailing to Koufonisia

There are daily departures from Piso Livadi port for people who only have a day to explore Koufonisia. The first part of the cruise is crossing the channel between Naxos and Paros. The first stop is at a picturesque bay on Naxos Island’s southern coast. That is a chance for the people on board to swim under the small chapel of Agios Sostis. The next route depends on the wind conditions, but the captain always chooses the best stop spots for people to snorkel and swim and, if lucky, see dolphins. The captain lights up the BBQ at around noon and offers the cruisers refreshments and a glass of ouzo. Cruisers also get to look at the beautiful Small Cyclades coastline with beautiful rock formations and the clear deep blue waters. At sunset, the captain turns and starts heading back to Piso Livadi.

Sailing to Antiparos

Departures are usually from Paros or Naxos. The yacht departs from Naxos at 9:30 am from the Port of Agia Anna, and Paros at 10:15 am at port Piso Livadi. The captain sails around the magnificent Paros coastline past Farangas and Tripiti. At 11:30, the captain stops at Panteronisia for cruisers to snorkel or swim. The next stop is at 14:00 at the south of Antiparos on a beautiful bay with rocks and caves where cruisers can go cliff diving, kiting, or swimming. The captain also offers cruisers BBQ lunch. At 17:00, the captain makes the last stop at Tourlos, a small island between Antiparos and Paros, for kitting and swimming. At 18:30, the journey back to Piso Livadi begins, and at 19:00, the captain heads back to Agia Anna.

Island Sailing in Greece

One-Day Cruise to Antiparos

An Island sailing Greece vacation is not complete without a cruise to Antiparos. The Catamaran Filippos departs Naxos at Agia Anna port at 9:30 am and Paros at Piso Livadi port at 10:15 am. During the trip, the captain has an inflatable tender that supports the swimmers in case of need. The first stop is at 11:30 at Panteronisia. At 14:00, the captain stops south of Antiparos on the beautiful bay and offers the cruisers BBQ lunch. The final stop is at 17:00 at an island between Antiparos and Paros, and at 18:30, the captain heads back for Piso Livadi. Finally, the journey to Agia Anna starts at 19:00.

Cruise From Pounta to Antiparos

Visitors staying at Pounta can enjoy a day of island sailing in Greece to Antiparos. The boat departs at 10:30 am, and cruisers can store their belongings on the boat. The first stop is at 11:30 on Panteronisia, where cruisers can snorkel and swim. At 14:00, the captain stops south of Antiparos and offers a BBQ lunch. The final stop at Tourlos is at 17:00, and the captain heads back to Pounta at 18:00.