Holiday Sailing Area: Sailing Itineraries

Thinking About a Sailing Trip in Greece? In Greece from May onwards, hundreds of boats and yachts sail the Aegean and the Ionian Sea, offering vacations with an unparalleled sense of freedom and connection with nature.


The Greek archipelago and the Ionian Sea are an attractive playground for novice and experienced sailors alike. There are countless secret coves and beaches that are only accessible by boat. Additionally, a chartered yacht can be a floating base for many other summer activities such as fishingdiving, and windsurfing. And when you get tired of the sea and want to get your feet back on dry land, all you need to do is point your boat in the direction of the nearest bay or harbor.


The itineraries in this section are the result of my extensive experience sailing in this area. If you are in need of special recommendations, quiet anchorage, unspoiled beaches, best beach bars, etc. feel free to send us a message. And if you have some interesting places that you want to share with us, feel free to post them on our Facebook or Instagram page with the #sailwithskipper and @ocean_Nomads tags.

Itineraries for the Greek sailing areas:

Yachting and Sailing Itineraries in the Cyclades

When sailing the Cyclades you have a couple of choices where to start.

You can start from Athens Alimos/Kalamaki Marina or Lavrion (Port Marina and Olympic Marina). The biggest selection of quality yachts in Greece can be found in Athens Kalamaki – Athens Alimos Marina. Lavrion Port Marina or Olympic Marina are situated further south on Attica and thus much closer to the Cyclades, but the downside is that there are fewer quality yachts available from Lavrion. Starting from Lavrion or Alimos/Kalamaki Marina also gives you an alternative in case of bad weather (Strong winds/Meltemi). With the Meltemi sailing the Cyclades can be challenging to dangerous, and alternatively, you can sail the Argo-Saronicos from Alimos or Lavrion instead.

The second option is starting in Mykonos or Poros. These islands are lying in the middle of the Cyclades so you start right in the center! If you only have one week and want to explore the Micro-Cyclades or want to visit the islands of the South Cyclades this is the place to start. The downside of these ports is that there is limited availability of quality yachts. When its “to”-windy there are no alternatives and you can only stay and wait for better weather.


The Ultimate Greek Cyclades Sailing cruise - 2 weeks: 390Nm

The Greek west Cyclades Sailing island tour - 1 week: 240Nm

The relaxing Micro-Cyclades yacht cruise - 1 Week: 132 Nm

The Cyclades and Argo-Saronicos cruise - 2 Weeks: 450 Nm

Yachting and Sailing Itineraries in the Argo-Saronic and East Peloponnese

There are several very nice 1-week cruises or itineraries in the Argo-Saronic. However, a 2-week itinerary opens up many more possibilities. And if the weather window for the Cyclades is challenging, I can even suggest a two weeks Cyclades-ArgoSaronic tour. When the Meltemi is blowing the Argo-Saronic is a nice alternative, although it can get a bit bussy.


Central Argo-Saronic island tour - 1 week: 130Nm

The Argo-Saronicos Archaeological Tour - 2 Weeks: 282 Nm

Facebook Reviews

Site Reviews

  • A fantastic week sailing! | Erik
    We are a family of 8 and wanted to sail for a week on the Greek islands. As we are not advanced sailors, we chose to hire a skipper. We had the luck to get Walter as a skipper in the Piraeus Marina, where we started for our week in the Saronic Sea. Arriving on Saturday, we started our sail ...
  • Sailing the Argo-Saronicos in July 2017 | Melissa
    My two daughters and I sailed with Walter and Aleka in the Argo-Saronic in July and couldn’t possibly have had a better experience. From the planning stages, it was a pleasure. He was helpful finding a sailboat that fit our needs and budget. We were very inexperienced in sailing, so his input led to the right boat and the right ...
  • Thanks to Ocean Nomads! Highly recommended!
    I had one week on board of “Argo”. Yacht is good, clean, and it is very easy to sail. Walter is an owner, and he assist with all issues. Great man and experienced skipper. Highly recommended! Stas Blokhin