Cyclades Islands Sailing Adventure Itinerary

Day 1 Board Your Sailboat in Athens

Your tour begins at the dock in Athens where you’ll board the sailboat and get settled in your cabin. The crew will give you a tour of the boat and a safety briefing before you set sail. The destination for your first sail will be Kythnos Island.

When you arrive at the port in Loutra you can visit the natural hot springs and enjoy dinner on this lovely island.
Overnight Location: Sailing yacht at Kythnos Island
Meals: None

Day 2 Cape Sounio/ Kythnos island – Serifos island

What better than a morning dive from the boat, under the imposing temple of Poseidon, before even taking breakfast?! After breakfast on board, you will set our compasses with direction the island of Serifos, where you can find the Cycladic simplicity you might be looking for.

In case you are in Kythnos, you can go on a morning hike, before setting sails to the unspoiled and charming island of Serifos (≈ 44nm, ≈ 6 hrs sailing).

Once we reach the port, we welcome you to walk with us uphill all the way to Chora, the main town of the island. It is a steep, yet short walk up and the views, especially from the Venetian fortress will captivate your senses! Stroll through the narrow streets and get lost in Chora! Enjoy your dinner in one of the traditional tavernas and why not, some drinks afterwards in one of the fancy bars.

Overnight Location: Sailing yacht at Serifos Island
Meals: Breakfast, lunch

Day 3 Serifos – Kimolos island

Today you will sail towards one of the least touristic and most authentic Cycladic islands, Kimolos (≈ 21nm, ≈ 3 hrs sailing). Kimolos is another volcanic island, whose name derives from the Greek word “kimolia”, which is translated into chank. The island is the perfect getaway for those looking to escape the crowds and enjoy peacefulness and tranquility, among some spectacular white sandy beaches and tiny villages.

You will spend the day anchored at one of its pristine beaches (depending on the weather), before reaching the port, from where you can walk to Chora, the main town, explore its narrow, cobbled streets and locally run restaurants and bars.

Overnight Location: Sailing yacht at Kimolos
Meals: Breakfast

Day 4 Kimolos – Polyegos island – Milos island

Right opposite Kimolos lies the small uninhabited island of Polyegos, a secluded paradise with turquoise crystal clear waters that will definitely captivate your senses. This will be your first swimming stop for today. You will have time to enjoy swimming, snorkeling, dives from the boat or simply relax on the deck and sip the sun.

You will then sail along the south coastline of Milos to reach the spectacular coves of Kleftiko, probably the most photographed beach of Milos and for a reason! Kleftiko is a former pirates’ hideout with imposing volcanic rock formations, countless caves and turquoise crystal clear waters, accessible only by boat or on foot via a hiking trail.

There will be time for swimming, exploring the numerous caves and enjoying lunch on board, before sailing towards the port of Milos, where we will spend the night.

Overnight Location: Sailing yacht at Milos
Meals: Breakfast, lunch

Day 5 Milos – Sifnos island

After breakfast on board, you can go on a morning tour around the island to see some more of Milos’ highlights, such as the moonscape-like Sarakiniko beach, the 2nd most well-known landmark after Kleftiko, the catacombs, the place where Venus de Milo was discovered, the ancient theatre and the picturesque fishing village of Klima with its colorful postcard – like houses (tour duration approx. 3hrs, at an extra cost).

You can then say goodbye to Milos and set sails to your next destination, the charming and aristocratic island of Sifnos (≈ 20 – 24 nm, ≈ 3 – 4 hrs sailing). The exact spot/marina where you will spend this evening depends on the weather conditions.

Once in Sifnos, do not miss the chance to visit the traditional and historic settlement of Kastro, a lovely cliff-top village, which literally means Castle. Kastro is built on top of the ruins of the ancient capital of the island, it has a strong medieval character and it offers spectacular panoramic views over the Aegean sea!

Overnight Location: Sailing yacht at Sifnos Island
Meals: Breakfast

Day 6 Sifnos – Kythnos island

After breakfast, you’ll set sails to Kythnos island, another hidden gem of the Cyclades that has managed to maintain its authentic character (≈ 38nm, ≈ 5 – 5.5 hrs sailing).

You cannot visit Kythnos, without going to the unique beach of Kolona, one of the island’s landmarks! Kolona is actually a strip of sand joining Kythnos with the islet of Agios Loukas, creating a landscape of unparallel beauty! Once there, you can enjoy swimming and snorkelling, as well as lunch at the only tavern on the beach. You can also walk all the way up on top of Agios Loukas islet and enjoy the panoramic views it offers.

Later you will head to Merichas, the main port of Kythnos, where you will spend the evening (unless you prefer to spend your last night before returning to Athens anchored at a secluded beach, gazing at the stars and enjoying all the tranquillity our sailing yacht can offer.

Overnight Location: Sailing yacht at Kythnos
Meals: Breakfast

Day 7 Sailing Day and Return to Athens

This morning you’ll start sailing back to Athens. Go for a final swim or snorkel during a stop on the way and enjoy a delicious lunch onboard.

When you arrive at the Lavrio marina you can visit some of the sights in Athens, and then return for your last night on the sailing yacht.
Overnight Location: Sailing yacht at Athens
Meals: Breakfast, lunch, dinner

Day 8 Disembark in Athens

You’ll have to check out of your cabin this morning and begin your journey home or continue on your Greek adventure. Book ahead to spend some extra time in Athens!
Overnight Location: None
Meals: None