Sailing Greek Islands – West Cyclades Route
Sailing Holidays greece, West cyclades
Cyclades is the region where Greek Islands holidays concept was born. It is where whitewashed houses with cupolas, blue window shutters and small fishermen boats were photographed first. From here these photographs spread throughout the world and now in every Greek holidays prospect you can see photos from the Cyclades.
The islands in this area are rather large but with rich coastline with plenty of bays to drop our anchor in. Most of these bays are lined with some small, white houses, sandy beach and rather arid hills encircling it. The water is crystal clear, tavernas are in every town and the life runs somewhat slower. It is not easy to get to these places as a tourist – one needs to take a ferry – so the tourism is somewhat less (except Mykonos or Santorini of course).
These Cycladic islands were inhabited already a few thousands of years ago and it can be seen and felt. Columns, ruins, old paths are visible here and there, sometimes in the most unexpected place. Luckily enough plenty of great anchorages are nearby. Seems ancient Greeks also loved sailing (our thesis).
join a sailing adventure into the Greek islands
We designed a longer than usual sailing route, ca. 180NM, to visit all the gems of the region. To have more time for exploration on land we plan sailing in the night once or twice. Imagine falling asleep to the sounds of boat sailing and waking up nearby a Greek island. This route will give you a great insight into what Cyclades have to offer: little and quiet Greek villages, islander towns, archeological sites, lonesome bays and wind, wind, wind. Meltemi, the prevailent wind, will make sure the longer distance of this route will be covered with ease. Pack your sun lotion as the wind, sun and no clouds is to be expected.
As always no sailing experience is needed to join as our professional skippers will introduce you to everything you need to know. The optional sailing course is absolutely free of charge, hands on and fun. More experienced sailors will be given some responsibility and can count on coaching too!
Feel invited to join us sailing in Greece, West Cyclades! And remember to check our other Greek sailing holidays.
“West Cyclades” Route
Includes:
7 nights sailing,
passionate skipper,
bed linen, towels, end cleaning,
SUP board and dinghy,
trustful damage deposit,
travel insurance.
Excludes:
cashbox contribution ca. 180 € pp (food, port fees, fuel),
flights/transfers.
Departure: Lavrion Port, or Marina Alimos (Athens), or Marina Poros
Nearest Airport: Athens (ATH).
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*To sail at other dates; to organize a private trip; to get in touch.
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Unique Anchorages
This region offers some of the most beautiful anchorages in Greece. Come and tell us if you agree.
A windy ride!
Cyclades region is known for it’s Meltemi wind. As our local sources state this is somewhat changing with the global climate change. However, it is still likely that we may ride the wild wind for a day or two. Do not worry, if the forecast will be too much, we stay put in port and enjoy the holidays on land.
Sunsets on Greek Islands
Sailing through the Greek Islands we have many chances to admire picturesque sunsets. Some in a lonesome bay, some on a hilltop with whitewashed houses around. In any case bring your favourite drink along, the magic is there.
History alive
On each Greek Island you can find remnants of history enclosed in a stone. Standing there sometimes for thousands of years already they are witnesses for passing time and a great way to touch the antiquity.
Seaside Tavernas
The best way to conclude a day of sailing in Greece is with some Greek food. And the most charming way is to visit a local taverna, very often situated just at the seaside or overlooking the port. Fishermen boats that in the morning brought the days catch are laying tied up and provide a beautiful background for a dinner we enjoy with our new sailing friends.
Highlights of Sailing Holidays in Greece, West Cyclades Route
What you can expect to do on this route.
evening strolls in greek towns
Visiting small and medium Greek seaside towns will be our evening programme for this sailing holiday.
history and monuments
In many places, sometimes appearing out of nowhere the remains of ancient civilization are to be seen.
summer chilling in a bay
Some nights we will spend anchored in a beautiful bay. A swim before breakfast is a must!
Itinerary for Sailing Holidays in greece
We are true to the discoverers` spirit and plan our adventures accordingly to the winds, the weather and your wishes. This means the order as well as some of stopovers may be different than presented below. Leave planning at home! The plan showed below is only an indicative itinerary and your trip may differ. Only the mad men sail against the wind!
Marina
Our meeting point is one of the marinas not far from Athens airport (Alimos, Lavrio or Poros). In a small coastal Greek town, we all meet, provision the boats, get to know each other on a Welcome Dinner and spend the first night on a boat. On the next day, Sunday, our Greek sailing adventure truly begins. We do the safety introduction, cast off lines, set sails and off we go! Into the Cyclades!
Milos
Prepare for something you have not yet seen. This is a gem of the region. Hard to reach and unspoilt.
Pollonia
A small peninusla covered with houses in front of which we drop our anchor. Go ashore, swim, snorkel, relax.
Prassa
This beach has won in 2024 “The Worlds Clearest Water” award. Let us sail there and verify that!
Serifos
One of the typical islands in the Cyclades with a Hora on the top of the hill. Hora is the term used for the “old town” in Greece. After a sailing day we approach the port of Serifos, moor and strengthten ourselves with a delicious Greek meal. For the ones who would like to explore the island a pleasant hike is within sight – hiking up to the Hora and admiring the view on the port and our boats.
Kithnos
A wonderful anchorage awaits. The small sandy beach separates two perfect bays. We drop anchor, raft up the yachts and enjoy the typical evening of shared food, fun, and night swimming.
Regatta
On Friday, the last day of our sailing trip, we have a regatta. Skippers will have taught you enough by now to let you sail the boat yourself. They are there to observe and help in emergencies but it is you and your crew who competes against the other crews.
Once the rush and excitement is over, we have the Captains Dinner (“the last dinner”) with all the crews and enjoy recalling stories from the last week, toasting for the regatta winners and savoring the last moments under the sails.
Keep the connection
Day 8 is the day to say goodbye. All the miles sailed, bays visited, skills gained and time shared with others will make us bond and build relationships. Cherish these, keep in touch and remember that your sailing tribe is there. See you another time!
What people say about Naleia
Thanks Naleia & Dominik for the greatest week of my summer! I am definitely coming back next season. ❤️❤️❤️❤️❤️❤️
Naleia is friendly, inclusive, environmentally friendly and genuinely care about the oceans they sail in.
Thank you for our 4th trip with you.
I'll be back! 🙂
Looking forward to the next trip!
One tip, do bring your seasick pills if you are sensitive to that. You don't want to recover from your seasickness while the rest of us is swiming in bioluminescent glow in the dark plankton and having an amazing time ;).
Cheers, Marga and Joao
The prospect of cooking was daunting but in hindsight a fun teambuilding routine. Nico our skipper was very professional and cool headed, with great communication and a tailored trip to the preferences of the crew (plus a great guy to hang out with socially which makes a big difference).
Definately look forward to sailing again with Naleia at some point!
Sailing is such a gentle way of traveling, you have to be in tune with nature. Our skippers managed to avoid most mass tourism by arriving at our destinations for the night just when everyone else was leaving. This meant that we had the most beautiful islands to ourselves. Thailand is such beautiful country and the islands we discovered were absolutely stunning. I especially loved snorkeling in Ko Ha.
On top of all the wonderful experiences we learned about sailing. Hoisting the main sail, standing at the helm, doing tacks, ankering etc are all very empowering experiences!
I absolutely loved the trip and am planning to go on other trips with Naleia!
All the details are well arranged, while leaving room for improvisation and adventure, as the skippers trace the best route according to winds and spots around. You’ll be part of the crew and learn sailing (it’s perfectly ok if you don’t have a clue 🙂
Incredible landscapes, interesting chats, games, nice villages, azure waters, swimming, snorkeling, relaxing, cooking improvisation and lots lots of fun!!
Amazing sailing trips with the best people from all over the world, and best destinations. If you like sailing don't think twice!
I definitely recommend travelling with them and for sure I’ll do it again.
Learning to sail – great!
Making new international friends – great!
Flexible personalised routes - great!
Professional organisation – great!
Beautiful Croatian scenery – great!
This is one of the most awesome ways to spend a hollidays and discover a country with another point of view. Life on the islands will make you experience for example the slowness of time, the saltyness of the seas, the tastyness of freshly cooked food, the lovelyness of lasting friendships, and the cozyness of spending time in the tiny boat quarters. The organisation is professional, yet flexible. Highly recommended! Hope to be able to join again in the coming years