8 days discovering the Greek Cyclades islands by luxury yacht

Set sail at Athens

Piraeus port is the largest in Europe

Mr Panos Pellas, captain of 53.54 metre motor yacht O’Rama has been actively involved in the marine industry for over 23 years. He first began on board the merchant marine vessel Pacific Trader from there he moved into cruise ships with Celebrity Cruises before entering into the world of luxury yachts. He has been captain of Seralia, Toxon, Sagitta, Charisma A, Andilis and Smile.

Throughout his career he has sailed extensively around Greece and its surrounding islands. Here he shares his experience of sailing from Athens down to the scenic Cyclades islands.

Athens – Mykonos

You will embark on O’Rama in Athens (near the port of Piraeus), and once you have met the crew and settled in to your quarters, the yacht will get underway. The first day will be a leisurely one, spent at sea as your yacht motors south-east to Mykonos. After six hours at sea you’ll reach the old port of Mykonos.

With the yacht moored up, you can disembark to explore the town and watch the sunset over the “Little Venice” quarter as you sip a cocktail in one of the many bars on the island (Galleraki is a firm favourite). Return to the boat for a traditional Greek dinner.

Picture courtesy of wisarut_ch/Shutterstock.com

Athens to Mykonos via Delos

The ancient amphitheatre in the island of Delos, steeped in Greek mythology and a UNESCO World Heritage site

As you settle down to an alfresco breakfast, the yacht will sail peacefully to the historic island of Delos for an organised sightseeing tour of the old town, one of the most important archeological sites in Greece.

You will then sail to Psarrou or Ornos, depending on how busy they are with other yachts. Here you will drop anchor and spend the day enjoying the yacht’s facilities. A good lunch option is the famous Nammos restaurant and beach club.

Later that evening you will sail over to Mykonos port to enjoy a dinner in town. Squallo, which is close to the yacht’s berth, offers an excellent view of the old harbour and the yachts.

Picture courtesy of Justin Black/Shutterstock.com


Sail to secluded Kalo Livadi beach, surrounded by golden stretches of sand, dramatic cliffs and crystal clear waters

Another morning, another alfresco breakfast in the Cyclades on your charter yacht. Life’s not so bad, is it? After breakfast you will sail to a suitable swimming spot (Ornos, Psarrou or somewhere equally enchanting). Arriving late morning, you will have time for a swim and some lounging in the sun.

If you want to do some exploring, scooters can be rented for the day, the tender can take you to Kalo Livadi for go-karting or guests can be disembarked to Ornos and have ready a taxi to take them to the city for shopping, and bring them back.

Return to the old port in the evening for dinner, either on board, or in one of the many restaurants there.

Picture courtesy of Evangelos Gagkos/Shutterstock.com

Mykonos to Paros

Naoussa, the most picturesque fishing village in the Cyclades

Depart for Naoussa on the nearby island of Paros, approximately two hours sail away. Naoussa is a tiny fishing harbour, packed tightly with traditional fishing boats and surrounded by restaurants and cafes. It is a typical Cycladic scene, with octopuses hanging up to dry, fishermen mending their nets, and all sorts of craft coming and going from the harbour.

You can take lunch on board, or step ashore and try one of the dozens of restaurants gathered around the harbour. In the afternoon, take it easy on board, explore the town, or take the tender to nearby Kolympithres beach.

Naoussa has some excellent clubs and bars, so if you fancy letting your hair down with a night-out, this is a good place to do it.

Picture courtesy of Natalia Bratslavsky/Shutterstock.com

Paros to Santorini

With its dramatic cliffs and pristine whitewashed buildings, Fira, Santorini is considered among the most beautiful in the Greek Islands

After another alfresco breakfast overlooking the harbour of Naoussa (which, interestingly, was once a Russian naval base in the 1700s), the yacht will set sail for Santorini, a couple of hours cruise to the south.

You will arrive at Fira , the main town of Santorini, in time for lunch (for a nice and tasty Greek lunch, the crew can arrange a reservation at Katina’s in Ammoudi). Spend the afternoon exploring the town, which is picture-postcard-pretty and very photogenic. Captain Pellas suggests dinner at the Sphinx restaurant, followed by some dancing at the Enigma nightclub.

Picture courtesy of lornet/Shutterstock.com

Santorini to Ios and Milos

Soak up the stunning panoramic ocean views on picturesque Ios

Set sail after breakfast for the beautiful Magganari Beach on the south side of nearby Ios island. This idyllic spot is perfect for a day in and out of the water, playing with the yacht’s toys and generally relaxing in the sunshine. The crew will attend to your every need, you will have lunch on board, and as the sun sinks towards the horizon you will pack up and head for Milos and the port of Adamas (Milos port).

You can take dinner on board, or head ashore to see what you can find there. There are bars and clubs close by, or you can kick back and relax on the yacht – maybe watch a movie or two.

Picture courtesy of Josef Skacel/Shutterstock.com

Milos to Kleftiko and Hydra

Hydra's energetic nightlife could rival that of the most hedonistic Greek islands

In the morning you will sail around to a lovley swimming spot on the south-west of the island called Kleftiko (not to be confused with the lamb dish of the same name). Kleftiko offers many caves, and some of them can be visited with yacht’s tenders.

After lunch on board, you will set sail to Hydra, a picturesque island with good nightlife. It’s several hours at sea, so make yourself comfortable and enjoy watching the Aegean sea slip beneath the keel. In the evening, head ashore for dinner and a wander amongst the cafes and bars.

Picture courtesy of Anastasios71/Shutterstock.com

Hydra to Athens

The Temple of Aphaea on the historic city of Aegina, commanding sensational views across the island to the sea.

On your last day in the Greek islands you will make your way leisurely back to Athens, possibly stopping at Aegina en route to look at the wonderful Temple of Aphaea. You will arrive back at O’Rama’s home port of Agios Kosmas in the afternoon for disembarkation.

Picture courtesy of Ivan Varyukhin/ Shutterstock.com

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