Explore Greece's Gems: Cyclades Sailing Trip for Thrilling Adventures

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7 Days30 Days!

Extra Cancellation Days
only for the first TripMate

Guided trip
What's special?
special Sailing Experience
special Embrace Nature in Tranquil Anchorages
special Foster Bonds & Lasting Memories
We will sail from island to island and bay to bay onboard my yacht that has just completed a sail around the world and is equipped with many nice toys like a SUP and a watermaker that makes life on the sea comfortable and chill. We will do a good mix of swimming around the boat in anchorages, visiting 1-2 island towns and explore there, visiting beach bars and Tavernas and maybe take a scooter to drive around an island. We will pool about 200 Euros per person at the start of the trip for the "crew kitty" to get food and drinks for the week and for marina fees and for re-fueling the boat at the end of the trip.

About Me! I am a 37-year-old German journalist who quit his job to sail around the world. I have also worked as a yacht skipper as a side job for 10+ years. I have also a masters degree in Political Science and Sociology. I am easygoing and uncomplicated as a person.

The boat has 4 double cabins. You share your cabin usually with another crew member of the same sex unless you want it differently. We also have 2 mattresses to sleep on deck and 2 hammocks. We have two bathrooms. In the middle of the boat is the salon with kitchen and big table with sofa area to hang out, cook and eat. Any questions about the trip? You can let me know in the Q&A section!

What's included?
Swimming toys
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Ex-Journalist and professional skipper

You can chat with Moritz once you reserve your spot.
Trip Itinerary


Day 1-2
We start our trip in the elegant island town of Poros with its long winding promenade full of sailboats and chic Cafes and Tavernas. Poros can be reached easily from Piraeus/Athens via a 1 hour ferry ride across the Saronic gulf that in itself is an experience. Poros is also strategically well-situated to reach the island-world of the Cyclades. But first we must do some food-shopping with the crew on day 1 to prepare for the week.


Day 2-3
The island of Serifos is one first stop on our way into the Cyclades. For instance we may anchor in an isolated bay on the south side where we can swim around the boat, climb up the hill with the goats to stretch our legs and enjoy the view - or make a beach bonfire in the evening and dance around it with a bottle of rum.


Day 3-5
In Kithnos, another entry point in the Cyclades we might stay 1 or maybe even 2 nights at the start or end of the trip. The amazing Kolona beach - a strip surrounded on each sides by water is famous, also for having volcanic springs where we can bath in a hot pool and then cool down in the sea.


Day 5-6
The capital city of the Cyclades is very Greek, you wont find (m)any foreign tourists here but otherwise a very nautical atmosphere with the shipyards, but also chic tavernas and a nice old town to stroll through before choosing a taverna for the evening.


Day 6-7
Milos is a possible stop if we sail southwards. In one day it is possible to see most sites by renting a scooter to see the white cliffs on the north coast, the windmills and the fields, the beaches of the south coast and the harbor town in the middle of this islands big natural harbor.


Day 7
At the end of our trip we sail back to Poros in a longer sunrise sail, a bit bigger dose of sailing to go back to our base. Back in Poros we either check out another taverna or cook the rest of the food we have and then explore town afterwards. Maybe we walk up to the clock tower to stretch our legs and enjoy the view over the sound.
Trip Summary
7 days trip
Poros, Serifos & 4 more
What's excluded?
Transport to start harbor
Diesel for boat
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