Greece: Sailing in Cyclades Archipelago

Aka. There and Back Again Route

Feel invited to join us sailing in Cyclades! This sailing trip is really adventurous! We are going to sail in the night, cover great distances (300+ NM) and enjoy the average wind speed of 13-14 knots! Because we want to visit Santorini (far away from Athens), we sail on this route for 10 days. Aside from enjoying our adventure on the yacht, we will visit the islands where a well-developed civilization was already thriving in the year 3000BC, dine on truly Greek cuisine and improve our sailing skills on this sailing focused trip.

In beautiful hillside towns we stroll through tight and winding streets between whitewashed houses with cyan-blue roofs and windowsills. The Cyclades are dry and arid islands. They have a striking austere beauty rising sky-high straight from the sea. We do however find an island covered with trees and spring-watered valleys, which we discover on scooters. The pick of the bunch is Santorini island, built around a volcanic caldera with it`s stunning sunsets and specialty wines.

Our Stops Enroute:


We start sailing in Cyclades with an easy day. We leave Lavrion marina and arrive to Kea island. This short passage (15NM) let`s us get used to the yacht and the crew dynamics.

Sailing in Cyclades - Kea.


From Kea we pass Kythonos, stopping for a lunch and sail further to enjoy one of many stunning approaches in the Cyclades: east side of Serifos island. We head to Livadi which is a safe harbour, with a pier and facilities for yachties. Overlooking Livadi is a small hillside village with beautiful whitewashed houses, from where we enjoy great sunset view.

Serifos - a nice stop on our sailing in Cyclades adventure.


Cliffs on Milos island are a perfect stop for a refreshing swim just before entering this ancient harbor.

Cliffs of Milos.

Port of Milos is built within a volcanic caldera (if this is not crazy I do not know what is!), formed by sea breaking into the volcanic crater. We get an idea of the caldera size while enjoying some relaxing moments in a cafe with a magnificent view.

Sunsets on Greek islands are always impressive! After such an experience, we walk down and socialize on yachts, preparing logistics for the Milos-Santorini night passage on the following day.


We leave to Santorini in the afternoon and sail through the night! Naturally the whole crew take turns watching and help to sail the boat. A blanket of stars on the open sea cannot be more beautiful! This is a wonderful way to spend your time!

Sailing in Cyclades. Night sailing.

Arriving to Santorini in the morning we have the whole day to explore. We visit the volcanic cone, try to touch the hot sulfur exhausts and stroll around tightly built houses. We dine out with one of the best views in the whole Aegean Sea! It`s definitely a highlight of sailing in Cyclades!

Santorini! Highlight of sailing in Cyclades trip.


Ios is halfway between Santorini and Naxos. We anchor in one of the bays, raft the yachts together and let the great moments come! Remember to bring music instruments!

Visit Ios with us! Sail in Cyclades!


Following the shores of Ios, we sail further to the greenest island of Cyclades: Naxos. There are green valleys to explore on scooters, a marina with facilities and the town for going out. Paradise ain`t it?

Naxos - most green ofCyclades archipelago.

Naxos´ east side rises to 1008m above sea level. The west side however rolls down slowly into the sea presenting fertile land and great sights. For example the ruins of ancient temples.


From Naxos we head back to our home marina. It is another night sailing shift with incredible views! In the morning, we arrive at one of the secluded bays on Kea island to enjoy breakfast on anchor before heading home.

Sailing in Cyclades - Kea island.

Join us on a Sailing Holiday in The Cyclades!

Always Included: Yacht, Skipper, Learn-to-sail, Insurances. ⛵️ 🌴 🌞

Greece Cyclades sailing trip

(10 nights on board)

Guaranteed Departures in 2020

03rd June – 13th June 2020, 984 910* € pp
23rd Sept. – 03rd Oct. 2020, 1162 910* € pp

*February Promo – for bookings made before 29.02.2020.

All trips + Cashbox ca. 180 € pp (groceries, port fees, fuel)

Greece | Aegean Sea | “Cyclades” Route

Start: Lavrio Marina, Lavrion

Join Us Sailing in Greece!


*To sail at other dates; to organize a private trip; to get in touch.

Most Frequent Questions


As we are going to sail in the night and sometimes spend more than 8 hours in a row sailing the boat, we advise having at least 3 days sailing experience in your logbook. You should simply know that you like to sail :).
We will naturally have days with no sailing at all, in order to explore the islands, but it advisable to know what you are signing up for! If you have never sailed and are still highly motivated to join, please do send us an email and ask for advice on how to prepare well for the trip.


At Naleia we plan as we go according to the weather conditions and all crews` moods. There is a set of places that we can visit, but the order and exact choice is only made each morning after verifying the weather conditions. Leave planning at home! We live for the moment!


We check-in on the first day of the trip at 17h00. You are naturally most welcome to come earlier and say hello! Your yacht is being cleaned for you at this moment so we need to wait a little. We leave the port on the next day.

We need to leave the boat on the last day of the trip, by 09h00. The boat will be back in port on the evening before.


There will be 2 – 6 yachts in Cyclades flotilla.

Join The Adventure !