Charter a Yacht in the Cyclades and explore Athens, Kea, Syros, Mykonos, Naxos, Santorini, Sifnos, Kithnos
The Cyclades is the most well-known and frequently visited Greek island complex in the Aegean Sea. From the familiar names of Mykonos and Santorini to lesser-known spots such as Sifnos and Kythnos, the Cyclades provide both charm and challenge for seasoned sailors that wish to harness the Meltemi winds.
This Greek island sailing charter itinerary will cover more than eight islands during our 7-night trip, starting and ending in Athens, and show you what the Cyclades has to offer outside of the most well-known islands.
The first stop on our journey is Cape Sounion, where we will make time to visit the Temple of Poseidon. After, we head towards the island of Kea, known for its challenging wind conditions and shipwrecks that line the seabed and attract diving enthusiasts. The next day is spent in Syros, the capital of the Cyclades and one of the most architecturally stunning islands to visit. On Day 3, you will set foot on Delos, an island where nobody can give birth or die. The island once served as a religious and cultural center and was the birthplace of the Olympian god Apollo.
From there, the cosmopolitan Mykonos is only a stone’s throw away, where there are just as many celebrities as there are stunning beaches and coves to retreat to and enjoy the water. The two major highlights of Naxos and Santorini are next on this Cyclades yacht charter itinerary. After a day on the water, you will arrive in Sifnos, a place you must dine in. Try out Omega3 and Maiolica for a gourmet experience that will stay with you for a lifetime. The last stop before Athens is Kythnos with the impressive Kolona beach.
A week will cover some but definitely not all of the highlights for your Cyclades sailing charter. If you wish to extend your trip to cover more destinations around the Cyclades and Greece, contact us and we can arrange a yacht charter based on your needs.
More ideals for yacht, catamaran, and motor boat charters in Greece here:
Cyclades Sailing Itinerary
Day 0 – Arrival to Athens, Greece
It is a brilliant idea to start your Greek islands yacht charter a day or two early, especially if your itinerary begins in Athens. Get a hotel in Plaka (the Old Town atmosphere) or on Lycabettus Hill (if you prefer views only). Note that in this specific charter itinerary, we’re going to Santorini from Athens. It is possible to start the week-long route in Mykonos and save on the distances (note that Santorini is approximately 130 nautical miles). Have a look at Acropolis, enjoy your evening in a Taverna in Plaka. We’re arriving on Friday, have a look at the Parthenon and stay in St George Lycabettus Hotel, which has beautiful views of the city and is located in the charming area of Kolonaki (clean, classical, streets full of citrus trees).
Day 1 – Athens – Sounion – Kea
Early in the morning, the arranged transport takes us to Agios Kosmas marina, the departure point of many motor yacht charters. We’re greeted by the crew and depart for Sounion. There is a lot of space in the bay. There is still some time before lunch, the braver of us are taken to shore for a quick walk up to the Temple of Poseidon, while the rest just chills on the yacht’s sundeck. The lunch is served and we depart in direction of Kea early after.
Kea has a lot of history, both ancient and modern. Being so close to the mainland and the first Cycladic island, Kea had strategic importance. Notably, Britannic (Titanic’s sister ship) was sunk off Kea, as it was on its way to pick up wounded allied soldiers, and its wreck still lies here. We choose a little bay with much fewer boats and have dinner. Most people are tired and jet-lagged, but a small group is ready to discover the area of Ay Nikolaos – a city with tavernas.
We’re making some plans for the next day. The historical sites of Kea, leading with the stone-carved 20ft lion, will have to wait for the next time. We’re ready for some watersports. The afternoon drinks turn into dinner and after-dinner drinks. A day well spent. We’re learning about the poet Simonides and physician Erasistratos – famous for the discovery that heart is not the center of sensation (as it was believed at the time), but a mere pump.
Day 2 – Kea – Syros
We’re starting the day with a glass of prosecco and salmon with capers. The water toys finally come down. We’re looking to try the 2 jet skis and the flyboard. Kids have fun in the water until lunch. The hoverboard is a bit trickier than expected, it will probably take a few days to get used to it. Surprisingly, the kids are the quickest to learn, probably because of the balance.
We’re leaving Kea after lunch. We’ve decided not to go to the capital of Cyclades – Ermoupolis – since we do come from a large city and not much remained of the historical city anyways. Instead, the captain chooses a calm bay for the day. We’re finalizing the place to spend the night. We will be spending the evening in Finikas, a well-sheltered bay in the NW part of the island.
There is much desire to get the water toys out again. Most of the adults are watching the kids from the sundeck, the jacuzzi is on. Some left on kayaks to discover the area.
Syros is mostly barren. We hear that the island was under the Venetians’ rule throughout much of the middle ages, replaced by the French. As a nice touch, a local anise sausage (French influence) is served with dinner. One serves all 8 guests. It is nice to try, but definitely not something we’d bring with us. Nevertheless, the local loukoumi is great, we’re wondering if we can buy some as souvenirs in the morning.
Day 3 – Syros – Delos – Mykonos
The next 3 days are the reason we actually chartered a private cruise in the Cyclades. We leave early for Delos. Next time, I’d probably want to go to Delos in the afternoon (because of the sun), but it’s still worth it. This island used to be the most important island of the Cyclades. There is evidence of that on each step. You can just imagine what the ancient city looked like, patches of ruins cover the island.
The Cyclades (Kukloi-rings) are formed around a central point, Delos – the last good anchorage between Europe and Asia, protected from the winds by Mykonos to the E, Rheneia to the W and Tinos to the N. The harbor extends half a mile into the sea. The commercial and religious importance of this biggest archeological site in the Greek islands goes back to around 500BC. Delos was not to be defiled by human birth or death, women were transported to Rheneia to give birth. The importance of Delos declined and power shifted to Rome to eventually be sacked in 80BC. Today, we can still get a good picture of what Delos probably looked like. You can move almost freely, Delos is not too crowded. The five lions guarding the sacred lake, the Temple of Apollo, the theatre, the remains of the harbor.
We’re leaving Delos and continuing on our journey to make it for sunset in Mykonos. We get to Little Venice just in time to find a nice spot and order coffee/ouzo, accompanied by the waves crashing just a few feet from us. Some amazing superyachts are anchored right behind us. Mykonos is a known place to meet celebrities. We decide to eat on shore tonight. The atmosphere of the place is accompanied by dancing, a few of us get to try the local Cycladic dances. A group of 4 is decided to see what the party is like, we’re wondering what is a realistic time to leave tomorrow morning. We missed the windmills, happy to have seen them from a distance.
Day 4 – Mykonos – Naxos – Santorini
We’re deciding to set sail early to have time in Naxos and get to Santorini with sunset. The crew saves some breakfast for the sleeping lot. As the last of us leave their cabins in the morning, we’re already close to Naxos. The charm and timelessness of the place are evident even from the marina, which is right next to the Old Town and the Apollo Temple. We don’t see too many tourists, it appears Naxos has been saved from mass tourism for now. We get out and go straight to the Temple, take pictures with the Portara – a majestic doorway that seems to be made for gods. Most of us go to the myriad little streets right after, making our way to the Venetian castle. Not much remained of it, but we fell in love with the little white and blue streets. We have late lunch and depart from the marina to continue on our route.
The yacht is well on the way to Santorini. We’re leaving the comfort of the aft deck to see the spectacle – we can already see by the contours of the island that Santorini is very different from the rest of the Greek islands we’ve seen so far. As we pass the outer ring of the giant volcano (all of Santorini is a giant volcano), we learn about the explosion that happened here 1642 BC. The Minoan eruption of Thera is connected to the Atlantis, which is supposedly underneath us. The explosion was so huge that it even wiped out the population of Crete.
We’re getting out at the old dock. We’re struggling to see if we should use the donkeys to get to the top. The struggle is real and we split into two parts, the children and women use the donkeys, while the rest of us gives the donkeys a break and take the cable car. We’re in main season and the city is a bit crowded. We decide to find a secluded cafe with great views. The sunset over the Mediterranean is spectacular, we finish our drinks and come back to the boat for dinner.
Day 5 – Santorini – Sifnos
We’re already looking forward to the next adventure of our luxury cruise. In the middle of the water-filled Thira crater is Tholos Naftilos. We move to the hot springs Nea Kameni on the west side of the island. The morning is dedicated to watersports. We’re getting much better with the hoverboard, some of us have already mastered it. This time we take some paddle boards out. So many things to see. We come back for the kayaks, but eventually, decide to take the RIB and go see the inside of the island. Steam escapes through holes in the ground, the volcano is definitely still active. Here we are, in the middle of an active volcano, on top of the Atlantis.
After lunch, we leave for the sulfurous springs, surrounded by red and yellow stones. The water is warm and getting the drinks from the RIB is really relaxing. We cover our bodies in the mud, kids have loads of fun in the process. Note that getting rid of the mud is much more complicated than putting it on. We need to leave, as we’ve reached the furthermost point of our Greece yacht charter itinerary and we need to return to Athens. As Santorini disappears in the distance, we open a few bottles of nice wine on the aft deck and take a little nap.
As the course of our cruise takes us past Ios, we learn that the island is the final resting place of Homer. The story is that the old blind Homer did not make the journey from Samos to Athens. As it was customary at the time, his body was thrown overboard and eventually got washed off on the beach in Ios. The Tomb of Homer is the one place we’ll have to miss, having spent a disproportionate amount of time around Mykonos, Naxos and Santorini. It would have been nice to see it, having seen the Prison of Socrates on the Acropolis.
We’re getting to Kamares beach in Sifnos, but we decide for a quieter place to spend the night. The plan is to get some watersports time the next day.
Day 6 – Sifnos – Kithnos – Athens
It’s the last full day of our Greek sailing vacation and the last chance to enjoy the watersports, which we take full advantage of. We’d like to be in Kithnos around lunchtime.
We arrive at Kolona beach, a wonderful sandbar beach connecting Loukas island to Kithnos. Most water toys leave the boat, as we spend the afternoon in the water, on the yacht’s sundeck and on the beach. We definitely need some downtime after the Delos-Mykonos-Naxos-Santorini bit, which was overwhelming. It had been advised that it might be a bit too much – I’d suggest you leave one of them out for your Greece island sailing charter.
The few hours at Kithnos pass quickly, we need to leave to arrive in Athens before sunset. We greet Sounion on our way back and follow the Peloponnese coastline.
Finally, we arrive at Agios Kosmas and have a splendid dinner that concludes our boat charter.
Day 7 – Athens
The final day starts with a generous breakfast. We’re sorry to say goodbye to the crew, they were truly amazing. The last coffee and the cars are already here to take us to the hotel. It has been a brilliant time. The captain recommends us charteting a skippered yacht in the Saronic islands next time, as it is more relaxed. The Ionian seems interesting as well, I’m sure the kids would enjoy the caves and beaches.