I venture on a sailing holiday in Greece every year with my best friends. Over the years I’ve got to know the islands and climate exceptionally well. I’ve visited pretty much every island in the Cyclades, and most in the Saronic too. I thought with my experience and knowledge I could provide you with a great 7-day Cyclades sailing itinerary. 

If you are looking to charter a yacht for your sailing holiday in Greece and want to visit the Cyclades, I would highly recommend chartering from Lavrion Marina. Lavrion is around an hour’s drive south of Athens, however, this translates to the best part of a day sailing. If you pick up your yacht here you can get ahead of the rush and it gives you a massive head start. 

7-Day Cyclades sailing itinerary

Day 1 – Lavrion to Kythnos 

Day 1 is all about picking up your boat, getting everything in order, and escaping from the mainland for your sailing holiday in Greece. Kythnos is a great spot to head, and you should arrive before sunset. There are two marinas, Loutra and Merichas. Both can get quite busy so I recommend getting there as early as possible. If you don’t find a spot, don’t panic, there are plenty of amazing bays you can anchor around Kythnos.

Day 2 – Kythnos to Paros

Paros is my favourite of all the Greek islands. There are two main towns, Naoussa and Parikia. Naoussa is very similar to Mykonos, with amazing winding cobbled streets, and endless amazing places to eat and party. My favourite spot to eat in the whole of Naoussa is Notos, some truly amazing fresh seafood and Greek cuisine. 

Parikia has a much more chilled vibe, stunning beaches, a few great beach bars and one or two places to party on an evening. This is the main port on Paros and has a much more touristic feel to it. The big ferries often drop hundreds of holidaymakers off twice a day. 

 

 

Day 3 – Paros to Ios 

Ios is among the most southern of the Cyclades islands. This picturesque island is exactly what you imagine. Stunning panoramic views of the ocean and sunsets like no other. Ios comes to life on an evening too, if you head into Chora after sundown you will be pleasantly surprised with the choice of restaurants, bars and shops to browse around. 

 

Day 4 – Ios to Milos 

Milos is growing increasingly popular over the last few years. Milos is home to the famous Sarakiniko beach and has some of the best scenery of the Greek islands. There are also some exceptional restaurants in Milos, my favourite being Mikros Apoplous. There isn’t a great amount to do on Milos, it’s a great place to chill out and soak up the Greek vibes. 

 

Day 5 – Milos to Sifnos 

Only a short sail which means you will get the best part of the day on Sifnos. Now, this place is beautiful. A great selection of seafood tavernas, a few bars and some great beaches. This sleepy Greek island will have you in awe. I recommend visiting Paralia Vroulidia, one of the most breathtaking beaches I’ve seen. 

 

Day 6 – Sifnos to Serifos 

If you are a fan of rugged countryside you will fall in love with Serifos. This unchanged island will be a great place to wind down after your amazing week. You could sit and enjoy an amazing fresh meal and a few drinks in the glorious Stefanakos Tavern, this place is serving up authentic Greek food in a stunning setting. 

 

Day 7 – Serifos to Lavrion

Unfortunately, all good things come to an end. On your 7th and final day, you will be heading back to Lavrion. This sail should take around half a day, so at least you can spend the morning on Serifos and enjoy the stunning beaches and amazing food Serifos has to offer. 

 

Final notes:

Whilst this would be my 7-Day Cyclades sailing itinerary, you don’t have to visit all of these islands, nor do you have to do it in the order I have given. Feel free to swap an island out, or if you feel like spending 2 nights on your favourite, skip the next one. This is what I love about sailing holidays in Greece, you have the freedom to decide where you want to go and when you want to do it, with a choice of over 6000 islands!

Enjoy!

PS – if you fancy writing some articles for us, please get in touch through my home page HERE