Two-weeks "Deep Cyclades" Islands Sailing Trip

Hosted by

Moritz

7 Days30 Days!

Extra Cancellation Days
only for the first TripMate

28 Jun 25 → 12 Jul 25

Guided trip

15 days

10 stops

4 - 7 Mates

Greece

What's special?

Sailing

Sunrise-Watching

Island-Hopping

Sailing two weeks allows us to go deeper into the island world of the Cyclades, past the must-see but well-trodden paths and islands of Kithnos & Milos, Mykonos and Santorini. We will also go to places you cant go withouth a sailing yacht, we will explore the hidden small islands and anchorages that are the reason why many people consider the Cyclades to be the heart of sailing in Greece. Explore and adventure around with our young crew of single travelers and roam around the beaches near our boat, swim around the boat and into caves, cook together and then watch the sunset, stroll through almost-forgotten island villages and the must-see bars of Mykonos or places like Santorini as well. And make new friends and memories, get your dose of Magical Ocean Sailing :-)

I am a 38-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 and I love teaching people sailing.

My sailing yacht Free Spirit is a professional charter boat that I run myself with all safety inspections and gear. I have sailed around the world with her the last two years and in 2025 we will sail in Greece - where I started in 2022. The boat has 4 double cabins, 3 of them have a queen-size double mattrass, one cabin has bunk-beds. If you don't come with a partner or friend to share the cabin with you will share a cabin with another crew member, usually of the same sex. Free Spirit also has a spacious salon equipped with a kitchen. On deck in the cockpit we steer the ship and eat. On deck , the boat has two big sun-tanning mattrasses and more space in the front to lay in the sun while enjoying the view and the feel of the wooden teak deck on your feet. Any questions about the trip? You can let me know in the Q&A section!

What's included?

Beddings

Towel

Swimming toys

Tender boat

Stand-up-paddle board

Your Booking includes free protection from Trip cancellations.
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Gallery

Greece - Poros - Two-weeks "Deep Cyclades" Islands Sailing Trip

Greece - Kithnos - Two-weeks "Deep Cyclades" Islands Sailing Trip

Greece - Ermoupoli - Two-weeks "Deep Cyclades" Islands Sailing Trip

Moritz

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Poros

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.

Kithnos

Day 2-4

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.

Ermoupoli

Day 4-5

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.

Naxos

Day 5-7

Be it in the backpacker-bars of Naxos town or rather anchoring at its nearby beaches: We will do what we are in the mood for. We might stop at another anchorage to explore more of this big amazing island.

Amorgos

Day 7-9

Anybody wants to go diving or snorkeling? Amorgos has amazingly clear water to do so. We will also look for the cute remote anchorages where we maybe even will have a bay just for ourselves to swim around the boat and soak in the sun and isolation.

Fira

Day 9-10

Its a must-see, so we will drive by too and explore the famous sunset-watching spot and watch other tourists ;-) But unlike them we dont have to sleep in crazy over-priced rooms but can go back to the boat after exploring the famous mountain village.

Folegandros

Day 10-11

We will start with a sunrise-sail to go to this off-the-beaten-path island and spend some more time at sea after the hustle-and-bustle of Santorini. Anchored in the clear waters of Folegandros, we do some chilling and swimming around the boat, maybe some cliff-jumping?

Milos

Day 11-13

From the white cliffs on the north coast and its amazing landscape via the high-lands to the beaches on the south-coast: This island is nice to explore with a scooter - something not to be missed on a sailing trip in Greece. It also has nice bars and restaurants in the harbor-town.

Serifos

Day 13-14

On the east coast of Serifos there are some of the most beautiful beaches in the Cyclades. Lets go there and enjoy the crystal clear water and some food in the beach taverna which overlooks the bay. The sporty ones might hike the island, the rest of the crew will just soak up the sun in the fine sand.

Poros

Day 14-15

We end our trip in the elegant island town of Poros with its long winding promenade full of sailboats and chic Cafes and Tavernas. Poros is a sailors town. With many others, we will strol along the promenade and have some food in a taverna in the evening to end the trip. Poros can be easily left via ferry to Piraeus/Athens.