A sailing adventure around the Cyclades Islands is an incredible way to explore some of Greece's most beautiful and iconic islands. This itinerary balances time for sailing, sightseeing, relaxation, and cultural immersion.
Day 1: Athens (Alimos Marina) to Kea (40 NM)
Highlights:
Depart from Athens’ Alimos Marina and sail towards Kea, a quiet island with beautiful beaches and quaint villages.
Relax in Vourkari Bay and enjoy dinner at a waterfront taverna.
Must-See: The ancient stone Lion of Kea and the charming village of Ioulis.
Day 2: Kea to Kythnos (Loutra) (25 NM)
Highlights:
Sail to Kythnos, known for its hot springs and peaceful ambiance.
Anchor at Loutra, a small village famous for its natural thermal springs.
Must-See: Relax in the hot springs at Loutra and explore the nearby beaches.
Day 3: Kythnos to Syros (Ermoupoli) (30 NM)
Highlights:
Head to Syros, the capital of the Cyclades, known for its neoclassical architecture.
Explore the lively port of Ermoupoli, with its cosmopolitan vibe, restaurants, and cafes.
Must-See: Visit the Apollo Theater and stroll through the charming Vaporia district.
Day 4: Syros to Mykonos (Delos Stopover) (20 NM)
Highlights:
En route to Mykonos, stop by the uninhabited island of Delos, a UNESCO World Heritage site and one of the most important archaeological sites in Greece.
After exploring Delos, continue to Mykonos, known for its vibrant nightlife and whitewashed houses.
Must-See: Explore the ruins of Delos and enjoy a sunset cocktail in Mykonos Town.
Day 5: Mykonos
Highlights:
Spend a full day exploring Mykonos, its beautiful beaches, windmills, and chic boutiques.
Enjoy the glamorous beach clubs or take a quieter route and explore remote beaches by dinghy.
Must-See: Windmills of Kato Mili and Paraga Beach.
Day 6: Mykonos to Paros (Naoussa) (20 NM)
Highlights:
Sail to Paros, a Cycladic gem with charming villages and crystal-clear waters.
Anchor at Naoussa, a picturesque fishing village known for its traditional tavernas and lively nightlife.
Must-See: Stroll through the narrow streets of Naoussa and visit the Venetian castle ruins.
Day 7: Paros to Antiparos (10 NM)
Highlights:
A short sail to Antiparos, a peaceful and less crowded island perfect for relaxing.
Visit the famous Antiparos Cave and enjoy the serene beaches.
Must-See: Explore the cave, known for its impressive stalactites and stalagmites.
Day 8: Antiparos to Sifnos (Kamares) (25 NM)
Highlights:
Sail to Sifnos, a foodie haven known for its traditional pottery and delicious cuisine.
Dock at Kamares port and explore the island’s picturesque villages.
Must-See: Visit the whitewashed monastery of Panagia Chrysopigi and sample local dishes like chickpea stew.
Day 9: Sifnos to Milos (Adamas) (20 NM)
Highlights:
Sail to Milos, famous for its colorful rock formations and unique volcanic landscapes.
Anchor at Adamas port, and explore the island’s breathtaking beaches like Sarakiniko and Kleftiko.
Must-See: Swim in the turquoise waters at Kleftiko, with its dramatic sea caves.
Day 10: Milos
Highlights:
Spend a full day exploring Milos, including the ancient catacombs and the site where the Venus de Milo was discovered.
Enjoy a day of swimming, snorkeling, or visiting the traditional fishing villages.
Must-See: Sarakiniko Beach and the ancient theater of Milos.
Day 11: Milos to Folegandros (Karavostasi) (30 NM)
Highlights:
Sail to Folegandros, an unspoiled island with dramatic cliffs and charming villages.
Dock at Karavostasi and explore the island’s capital, Chora, perched on a cliff with stunning views.
Must-See: The Church of Panagia, located high above Chora, offers panoramic views.
Day 12: Folegandros to Ios (20 NM)
Highlights:
Sail to Ios, a party island with a relaxed vibe during the day and lively at night.
Explore Ios Town’s whitewashed houses and beautiful beaches like Mylopotas.
Must-See: The tomb of Homer and sunset from Chora.
Day 13: Ios to Santorini (Thira) (25 NM)
Highlights:
Head to the iconic island of Santorini, with its dramatic cliffs and white-washed houses overlooking the caldera.
Dock at the port of Athinios or Vlychada and spend the day exploring Oia and Fira.
Must-See: Sunset in Oia, the archaeological site of Akrotiri, and a hike along the caldera path.
Day 14: Santorini to Athens (Alimos Marina) (120 NM)
Highlights:
Depending on your departure time, spend the morning in Santorini before starting the long sail back to Athens.
Reflect on the beauty of the Cyclades as you return to Alimos Marina to conclude your adventure.
Tips:
Wind Conditions: The Meltemi winds can be strong during summer, especially in July and August. Be prepared for changes in the sailing plan based on wind conditions.
Provisioning: Stock up on supplies in larger ports like Syros or Paros.
Dining: Greek tavernas are an essential part of the experience, offering fresh seafood and local dishes. Try traditional Cycladic dishes such as fava in Santorini, mastelo in Sifnos, and koufeto in Folegandros.
This itinerary blends vibrant nightlife, cultural exploration, and serene landscapes, making it a comprehensive Cyclades sailing adventure.
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