Good Morning Greece! – 2 Week sailing itinerary for The Cyclades

Hello, sailors! Say good morning Greece and welcome yourself to the mesmerising realm of the Cyclades. Embark on a 14-day odyssey through this enchanting archipelago, where each island presents a unique charm and a story waiting to be discovered. From the iconic blue-domed churches of Santorini to the vibrant nightlife of Ios, this itinerary promises an unforgettable journey through the heart of the Cyclades, where every port of call unveils a new addition of Greek beauty and culture. So hoist your sails and let the winds of adventure carry you through this timeless Mediterranean paradise!

Good Morning Greece: Day 1: Athens

Begin your sailing adventure in the vibrant city of Athens, a city full of history and culture. Spend the day exploring iconic landmarks such as the Acropolis, crowned by the majestic Parthenon, and delve into the rich tapestry of ancient Greek mythology at the Acropolis Museum. Wander through the charming streets of Plaka, lined with neoclassical buildings while soaking in the lively atmosphere of Monastiraki Square. In the evening, savour authentic Greek cuisine in a local taverna, accompanied by live music and traditional dances. Finally, retire to your yacht to prepare for the journey ahead. As the sun sets over the city, prepare yourself for setting sail for the Cyclades in the morning.

Good Morning Greece: Day 2: Athens to Kithnos 55NM | 7HRS 51MINS

Set sail from Athens and head to Cape Sounion, where you will find the Temple of Poseidon, which can be seen from a distance and is easily reached by foot once ashore. The ideal time to visit is in the morning before the tourist crowds arrive. Arrive at Kithnos and drop anchor in one of the island’s bays such as Ormos Kolona and Ormos Fikiadha. Otherwise, dock at the picturesque port of Merichas. Relax on Kolona Beach, a unique strip of sand connecting Kythnos with the islet of Agios Loukas, offering breathtaking views of the sea on either side. Spend the afternoon exploring the whitewashed villages of Chora and Driopida.

Good Morning Greece: Day 3: Kithnos to Serifos 4HRS | 15MINS

Rise with the sun and set sail from Kythnos towards the rugged beauty of Serifos, a typical Cycladic island. Arrive at Serifos and anchor in the main harbour of Livadi. Spend the afternoon wandering through the narrow streets of Chora, which is situated at the top of the harbour, overlooking the sea with a magnificent view. Also, visit the imposing Venetian castle, dating back to the 13th century. 

As evening descends, dine at a traditional taverna in Livadi. After dinner, stroll along the waterfront promenade, watching the lights dance on the surface of the sea. At last, return to your yacht for a peaceful night’s sleep under the starlit sky.🌟

Good Morning Greece: Day 4: Serifos to Sifnos 1HRS | 50MINS

Prepare to depart from Serifos and continue your journey towards the captivating island of Sifnos. Drop anchor at Kamares or Agios Yeoryios. Spend the day exploring the island’s capital of Apollonia, dedicated to the god Apollo. Visit the historic monastery of Panagia Chrissopigi, one of the 300 churches of the island, and the old capital Kastra. In addition, visit Artemonas surrounded by hills full of windmills. In the afternoon, head to one of Sifnos’ beautiful beaches, such as Vathi or Platys Gialos. There you can swim, snorkel, or simply relax in the sun.🤿

Good Morning Greece: Day 5: Sifnos to Ios 5HRS | 34MINS

Set sail from Sifnos in the morning and arrive at Ios, known for its vibrant nightlife, stunning beaches, and traditional Cycladic architecture. Drop anchor in the sheltered bay of Ormos, the island’s main port. Here, whitewashed buildings cascade down the hillside to meet the sparkling sea. Otherwise, moor at Ormas Koumbaras, Ormos Milopatamou, Ormos Manganari or Ormos Tris Klises.

Spend the afternoon exploring the narrow streets of Chora, Ios’ main town. Visit the hilltop church of Panagia Gremiotissa, where you can enjoy great views. In the evening, immerse yourself in Ios’ legendary nightlife scene, with its beachfront bars, clubs, and live music venues. Dance the night away under the stars, sipping cocktails and mingling with locals and fellow travellers alike.

Good Morning Greece: Day 6: Ios to Santorini 3HRS | 17MINS

Depart from Ios in the morning and set sail towards the iconic island of Santorini, renowned for its breathtaking caldera views, stunning sunsets, and picturesque villages perched on cliff edges. Anchor at the port of Skala Thira. From there, sit comfortably on a donkey and climb up to Fira, the capital. Experience this charming town with its old Frankish quarter and its magnificent view of the bay where you can see Kamenes, two tiny islands made of lava. 🔥

Thirassia is also worth visiting, the second largest island left from previous eruptions. Make sure you also visit Oia, famous for its iconic blue-domed churches and stunning sunset views.

Good Morning Greece: Day 7: Santorini to Folegandros 3HRS | 55MINS

Bid farewell to Santorini and set sail for the tranquil island of Folegandros, a hidden gem in the Cyclades. Arrive at the port of Karavostasis and head inland to the main town Chora, perched on a cliff overlooking the sea. Visit the historic Church of Panagia and admire its stunning Byzantine architecture and the surrounding countryside.

In the afternoon, relax on one of Folegandros’ beautiful beaches, such as Agali or Livadaki. As the sun begins to go down, enjoy a delicious dinner at a seaside taverna, sampling fresh seafood and traditional Greek dishes while watching the sunset.🌅

Good Morning Greece: Day 8: Folegandros to Milos 5HRS | 42MINS

Raise anchor from Folegandros and arrive at Milos. Drop anchor in one of the island’s secluded bays or dock at the port of Adamas. Spend the day exploring the unique geological formations of Milos, including the iconic moonscape of Sarakiniko Beach and the colorful rock formations of Kleftiko.

Discover the island’s rich history and culture at the archaeological site of Ancient Milos, where you can explore ancient ruins dating back to the Classical and Hellenistic periods. In the evening, dine at a seaside taverna in Adamas, sampling local specialties such as fresh seafood and traditional Greek mezes, accompanied by a glass of chilled Assyrtiko wine.🍷

Good Morning Greece: Day 9: Milos to Hydra 9HRS 15MINS

Depart from Milos in the morning and set sail for Hydra. An island with many admirers, among the international community of writers, actors and artists in general. Perhaps because of its unique charm, or perhaps because of its rare combination of simplicity and sophistication. You can moor in Hydra main harbour, but we suggest getting there early as it is a favourite for the Greeks. Other mooring places include Mandraki, Petassi, Ag. Nikolaos, Nisis Dhokos and Ormos Skindos.

For a taste of adventure, hike to the Monastery of Profitis Ilias, perched high above Hydra Town. You can walk, under the shade of grapevines, or on narrow cobblestone streets almost to the top of the steep hills. Or you can just rest, lying on a rock by the sea. Hydra, with its well-preserved architecture, its numerous churches, and its donkey transportation, is one of the most picturesque islands in Greece.

Good Morning Greece: Day 10: Hydra to Poros 1HRS | 47MINS

Prepare to embark on the next leg of your sailing adventure towards the charming island of Poros. Just two or three miles off the mainland shore, stands Poros, decorated with green hills that reach the sea and main port with numerous seaside cafés and tavernas. An ideal spot for those who want both a quiet swim and intense nightlife. Across the water, on the Peloponnisos shore, you can enjoy an evening stroll among the lemon trees in the renowned ‘lamonodassos.”🍋

Good Morning Greece: Day 11: Poros to Epidavros 3HRS | 08MINS

Continue your sailing expedition towards the historic town of Epidavros. Head to Epidauros Marina on the north-eastern Peloponnese coast in Argolis. From there, explore the huge 4th century amphitheatre with its impressive, intact stadium, rising up in perfect symmetry. This ancient ruin, together with Mycenae, are important archaeological sites in Greece. Make sure you snorkel the sunken city of Epidauros to see ancient underwater ruins.

Visit the Sanctuary of Asklepios, dedicated to the Greek god of healing. Wander through the archaeological site, where ancient temples, sanctuaries, and baths offer a glimpse into the religious and therapeutic practices. After dinner, take a leisurely stroll through the town while soaking in the charming ambiance of Epidavros. Admire its historic architecture and serene atmosphere under the moonlight, before returning to your yacht for a peaceful night’s sleep.

Good Morning Greece: Day 12: Epidavros to Aegina 2HRS | 08MINS

Depart from Epidavros in the morning, bidding farewell to its archaeological treasures and serene harbor. Allow the gentle breeze to guide your yacht across the sparkling waters of the Saronic Gulf, towards Aegina. Aegina is the closest island as you depart from Kalamaki marina and is usually the first or last stop of your trip if you are sailing the Saronic Gulf. Explore the town of Aegina and visit The Temple of Alphia. You can go by taking the bus from the main harbour or moor in Agia Marina and take the caique. This is one of the most beautiful classical temples in Greece with its impressive Doric architecture.

As the sun begins to set, watch the fishing boats return to the harbour under the golden hues of the evening sky. Before you leave for your return to Athens, don’t forget to stock up on pistachios as they are produced on the island of Aegina and are probably the best in Greece!

Good Morning Greece: Day 13: Aegina to Athens 2HRS | 17MINS 

As the final day of your two-week sailing holiday dawns, it’s time to make the journey back to where it all began – Athens. Depart from the picturesque island of Aegina in the morning, filled with memories of the stunning landscapes, charming villages, and captivating history you’ve experienced throughout your sailing adventure in the Cyclades and Saronic Gulf.🌊

Arrive back in Athens, greeted by the iconic landmarks that define this ancient city – the Acropolis towering above, the bustling streets below, and the vibrant energy that pulses through its veins. Dock your yacht and take a moment to savour the sense of accomplishment and fulfilment that comes with completing such an unforgettable journey. Reflect on the sights you’ve seen, the experiences you’ve had, and the connections you’ve made along the way.

As you make your way back home or to your next destination, carry with you the spirit of exploration, adventure, and discovery that defines the magic of sailing in the Greek islands with Click&Boat!⛵