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Greece is one of the world’s most popular yachting destinations. It boasts vast waters to cruise while visiting both ancient and modern attractions from museums to archaeological sites, excavations, and ancient cities, all of them historical monuments, which have inspired modern education and culture around the world.

Greece has a total of around 2,000 islands, of which only 168 are inhabited.

The country is surrounded to the east by the Aegean Sea, to the west by the Ionian and to the south by the Southern Mediterranean Sea.

The most popular cruising grounds are the islands of the Aegean Sea, are situated between mainland Greece and Turkey to the east. Traditionally, the Greek islands are classified into seven groups, from north to south: North Aegean Islands, Sporades, Euboea, Saronic Islands, Cyclades, Dodecanese, and Crete.

After spending years cruising and exploring these small islands we have chosen our favorite chain, the Cyclades islands, and provided a week long itinerary which can be modified in any way to suit your vacations needs.


One of the largest tourist attractions in Greece is the island of Mykonos. Here you can fly into the international airport and join the yacht which will either be located in Ornos or the Port of Mykonos town, depending on wind direction. We highly recommend a tour of Mykonos town either that evening or the next morning. The town of Mykonos is an experience in itself with its Narrow Streets and beautiful architecture. They also have a wonderful Maritime museum here in the town.


The next day you can go to Agrilos beach on Mykonos, the nicest beach in the area or perhaps you are in the mood for a party at the famous “Paradise beach” located on the south side the of the Island.

The next Island will be Paros 20nm away, the first anchorage here is on the North side, Naousa, and is beautiful with turquoise water and a quaint little town, which is nice for an afternoon stroll. After Naousa, you will sail around o Anti Paros and anchor off the small town of Spyidon with its winding streets and typically Greek lay back atmosphere.


From Paros you will sail to the Islands of Naxos which is about 2 hours away. This is the most fertile island of the Cyclades chain. From the sea the island appears to be rocky and bare, but inland the island is wooded and cultivated. The island has two mountains with beautiful valleys and slopes terraced with olive and citrus orchards. We anchor in the port of Naxos here. Stroll along the shore or visit an authentic Greek taverna and experience the amazing grilled octopus or fresh fish that the region has to offer.


After Naxos we will head to the island of Iraklia which is about 20nm, or one of the Small cluster south of Naxos known as Schoinousa, Koufonisos, Koufornisi, Nisida. All very much off the beaten path and very much worth a visit, especially if you want to experience tiny, quiet, cute and isolated places that represent the true Greek spirit. The beaches and coastline are well protected and there are never many tourists around these Islands

From Iraklia, you will head to “Ios”, about 21nm away. This Island is prized for the location of Homer’s tomb and the excavated site of Skarkos. This island is rich with history and archaeological sites. The coastline affords visiting yachts an abundance of places to anchor and at the south end of the Island is the bay of Manganari. This huge bay with the clearest turquoise water and white sand  is a favorite of ours and is a great place to spend the night before the big sail to Santorini, which you can see looming in the distance.
After a morning swim the captain and crew will prepare the boat and set sail to the Island of Thira (Santorini). Be sure to record this day as much as possible by video and photographs as it will be quite a day and for most, a dream come true!


Sailing into Santorini is so amazing that it leaves you standing in amazement. As the wind blows you along inside the enormous Volcano rim, topped with white houses and villages, you cannot escape the feeling of spiritual presence. The history books will tell you many amazing things about this Island.

Thira is our favorite Island for many reasons and depending on the size of the boat you charter; will depend on the amount of time you can spend here. There is a small Marina on the south shore that we know very well and can accommodate many bare boats and even a shallow draft 73ft catamaran or two, but it is officially a fishing port so operates on a first come first serve basis. If you can’t get in, the captain can take the boat to Akritori Beach and anchor very close to the land where the sea is much calmer. From this location, we highly recommend spending the rest of your vacation using the boat as a day sail boat and reentering the Caldera in the morning, being dropped off in OIS and meeting the boat back in Akritori Beach at the end of the day. You can visit the second largest, but the most exclusive town on the Islands in the morning and move to Thira for the sunset. If you’re lucky, and the sky is clear, you may just get to see the most beautiful sunset of your life. I have only seen one better in 25 years of sailing around the world, and it was from Bodrum, Turkey. Only 100 miles away!


We strongly recommend renting Quad bikes and spend your day buzzing about the rim of the Volcano. The roads are very good and the scenery is unimaginable. If local pottery is of interest to you, be sure to stop in the road side Art shops. The technique and style is defined by the resistance of the Santorini clay as it can be heated much higher than normal clay and is therefore much stronger and resilient.

There are several other anchorages that can be visited in Thira, depending on very precise variations in the weather. But if the opportunity arises. We strongly recommend visiting the East Coastline and stopping at Kamari Beach. If the wind is from the North West to West, this beach is a Wonderful place to spend the night. It’s also close enough to the airport that the departing commute doesn’t take too long. Otherwise, the dock master in the Marina will arrange a Mercedes Minivan to take you from Vlahada Marina.

We highly recommend leaving the last 2 days of your trip to visit Santorini. There are so many stunning places to go between all 4 sections. Lunch on the beach on Thirasia is another fantastic experience. If the captain times it right, you may even be able to stay there for the night, witnessing Santorini at night from Inside the Caldera is something else!

If your interested to do a trip like this. We highly recommend doing it in either June and Sept. As the winds and sea state are much lower during these months.

Any type of boat is ideal for a southbound Aegean Cruise but Stability and reliability are very important. Also a boat that carries a lot of chain, will be able to make use of good anchorages. A catamaran is an excellent choice but also the Turkish Gullets cope very well with the Aegean conditions. They were after all, made to operate in the area.

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