Sailing Greece: A Tour of Milos on a Traditional Wooden Boat

Reading Time: 4 minutes

Table of Contents

Want to sail the Greek islands on a traditional sailing ship? Maybe you like being in boats, but you don’t want to buy your own? Milos Trips is the ideal opportunity to sail in the Aegean Sea.

What is Milos Trips?

Milos trips is a family-run company in Milos that offers sailing experiences on Milos Island. They offer cruises around Milos and the surrounding islands in traditional wooden sailboats.

Stella and Stamatis

The Ship: Thalassitra

Thalassitra is a traditional wooden sailing ship which was completed by the owner, Mr. Lillis, who has a passion for the sea and since he was a small child, he dreamed of sailing on the waves of the Aegean.

Photo by Thalassitra Sailing
Thalassitra on the Right | Photo by Thalassitra Sailing

Thalassitra’s Sister: Leloudo

Leloudo is a traditional wooden boat that is usually referred to as the “sister” of Thalassitra. The owners of Leloudos and Thalassitra are brothers. Leloudos runs a similar route to Thalassitra and makes a daily trip around Milos, with a visit to the island of Polyaigos.

Leloulo in Red | Photo by Thalassitra Sailing
Sailboats in Greece | Photo by Thalassitra Sailing

What Happens on Your Tour?

What exactly do Thalassitra and Leloudo offer on their cruises? The journey starts from the port of Milos (Adamas) and follows a route around the islands of Milos and Polyaigos. During the journey, the boat stops at beaches and sea caves, which are only accessible from the sea.

 

You can take photos, swim in the crystal clear waters, and enjoy the hospitality. Traditional food is prepared before your eyes as you travel. High-quality ingredients and local products are the focus of the trip.

 

Breakfast, Lunch (buffet with 10 different local traditional dishes and salads), sweets, coffees, beers, and soft drinks is offered. During the stops, you can swim as much as you like and there is also equipment for snorkeling. There is also a tour guide, who will inform you about the history of the places you will see.

Photo by Thalassitra Sailing

Booking a Trip

The boats normally depart from the port of Adamas every day at 9.30 am. and return around 7.00 pm. Depending on the weather, the boats may also depart from Pollonia or Paleochori. The tours include stops at the top beaches and parts of Milos.

 

You can book a trip here.

Photo by Thalassitra Sailing

About Milos

Milos Island is like the little sister to Santorini. It is located nearby in the Cyclades and is known for its whitewashed houses and legendary sunsets. Out of all the islands with white buildings in Greece, it is less visited when compared to Santorini, while also being close to Athens. There are many caves and volcanic rock formations that kids love to explore, and also hidden caves where pirates used to hide.

 

About the Stops

Kleftiko

The famous cove of Kleftiko is a popular spot on Milos island and used to be a pirates’ hideout. It is known for its pristine water, its network of caves, and incredible rock formations. During the summer, many boats stop here because it is only reachable by boat.

Photo by Thalassitra Sailing
Kleftiko | Photo by Thalassitra Sailing

Sykia Cave

Thalassitra also stops at Sykia Cave, which is special because the roof has collapsed. There is a round opening that acts as a natural skylight, and the cave lights up from this unique feature. This is the biggest sea cave of Milos and is found in the southwest area of the island. The only way to reach Sykia Cave is by boat, and only small boats can enter through the passage. 

Photo by Thalassitra Sailing
Sykia Cave | Photo by Thalassitra Sailing

Polyaigos

Polyaigos roughly translates to “island full of goats” and it is the largest island of the Aegean without residents. It is unique for its wild landscapes, stunning beaches, and untouched natural beauty. It is a great destination for a day trip from Milos, especially for swimming.

Sailing in Greece

The Aegean is known for its strong winds, also called the “Meltemi.” The Meltemi are a katabatic wind that comes down from northern Greece and shoots through the Cycladic islands. The Meltemi peak at 15-20 knots. As a general rule, they start in the early afternoon and die down in the evening, but can also blow for multiple days nonstop. 

The Cycladic islands, including Milos, are affected by the Meltemi, especially when the land heats up in the summertime. The Meltemi winds fade away in the Autumn, making for good late-season voyages.

Looking for something in particular?
BlogLifestyle

Exotic Fruits in Greece That Will Surprise You

Most people associate Greek produce with olives, grapes, or citrus fruits like oranges and lemons. But did you know there’s a surprising variety of exotic ...
Nafplio
Regional Guides

Nafplio: A timeless destination to call home

Where history, lifestyle, and smart investment meet In the heart of the Peloponnese, just under two hours from Athens, lies Nafplio: A city that combines centuries ...
Expat working remotely in Greece with a sea view
BlogRegional Guides

Working and Living in Greece as an Expat

Have you ever thought of working and living in Greece as an expat? For many people, Greece is more than a summer escape; it’s a ...
Elxis at the Second Home Expo
BlogIn The News

Second Home Expo: Meet Elxis in Ghent

Dreaming of a holiday home abroad? The Second Home Expo in Ghent (Belgium) is where it all begins. On October 11 and 12, 2025, Flanders ...
BlogPress Releases

Press Release: Elxis – At Home in Greece: New Thessaloniki Offices Now in Operation

A few days ago, Elxis – At Home in Greece (https://elxis.com/) inaugurated its new offices in Thessaloniki, having moved to a larger and more comfortable ...
Homeowner calculating rental income tax Greece savings in 2026
BlogIn The News

How Upcoming Tax Changes Benefit Property Owners in Greece

During the 89th Thessaloniki International Fair, the Greek Prime Minister Kyriakos Mitsotakis announced several property tax changes that directly affect primary residence owners and potential ...
Your search results

Compare Listings

Featured in

Receive the latest news

Join over 20.000 subscribers and stay informed on the latest market insights, updates, tips and more

We’ll send you our best articles, expert insights and newest listings.​

Personalized Greek Real Estate Guidance

Tell us more and our team of real estate specialists will get in touch! 

This quick form takes less than a minute to complete. We only need minimal information to get started.

Step 1 of 3

Your inquiry will be reviewed within 24 hours on business days.