Cyclades Sailing Escape – Kea, Serifos & Milos
7-day round trip from Athens through iconic Cycladic islands.
Explore ancient sites, secret beaches & picturesque villages with a private skippered yacht.
Starting Point & Return: Athens
Discover the True Magic of the Aegean
Set sail from Athens and discover the raw beauty of the Cyclades on a carefully crafted Cyclades sailing trip. This Cyclades sailing trip offers a perfect blend of adventure, relaxation, and island hopping across Kea, Serifos, and Milos.
You’ll visit Kea, Serifos, and Milos — each island offering a different kind of charm.
Kea invites you into its timeless Chora and peaceful beaches.
Serifos welcomes you with dramatic cliffs, Cycladic architecture and golden bays.
Milos stuns with volcanic caves, colorful fishing villages and crystal waters.
Whether you’re swimming in hidden coves, walking through ancient ruins, or dining under the stars in a quiet harbor, this trip offers the perfect mix of freedom, discovery and Greek island magic — all from the deck of your private sailing yacht.
Waypoint 1: Athens → Kea
35 nautical miles | ~4–5 hours
Depart from Athens and head southeast toward Kea, the first island of the Cyclades. Relax with an easy first sail and enjoy a calm anchorage in a peaceful bay.
Waypoint 2: Kea → Serifos
35 nautical miles | ~4–5 hours
Continue deeper into the Cyclades as you sail southwest toward Serifos. Expect scenic views, open waters, and the iconic white-washed Chora rising above the port.
Waypoint 3: Serifos → Milos
30 nautical miles | ~4–5 hours
Sail south to reach Milos — known for its volcanic rock formations, sea caves, and colorful fishing villages. A mix of sailing and exploring awaits.
Return Option A: Milos → Kea (Kavia Bay)
55 nautical miles | ~7–8 hours
Start your return with a long but rewarding sail back to Kea’s northern bay for a final night under the stars.
Kea → Athens
40 nautical miles | ~5 hours
Finish your journey with a smooth sail back to Athens across the Aegean.
Nov 09, 2017
Return Option B: Milos → Aegina (Agia Marina)
75 nautical miles | ~9–10 hours
Alternative return route toward the Saronic side. Long open sea crossing ending at lively Aegina.
Aegina → Athens
15 nautical miles | ~2 hours
Short final sail back to Athens, perfect for a relaxing last day on the water.
This Cyclades sailing trip combines iconic landscapes, rich local character, and smooth daily routes — ideal for travelers seeking authenticity with comfort.
Trip Highlights
Each island on this Cyclades sailing route reveals a different face of the Aegean — from traditional villages and dramatic hilltop views to volcanic beaches and historic sites.
Explore below what makes Kea, Serifos and Milos unforgettable destinations for every sailor and island lover.
Explore Chora: Walk through Kea’s traditional hilltop village with stone alleys and panoramic views over the Aegean.
Lion of Kea: Visit the famous ancient lion sculpture carved into rock — a mysterious landmark over 2,500 years old.
Koundouros Beach: Anchor at one of the island’s most popular bays, perfect for swimming and sunbathing in calm waters.
Snorkeling & Wrecks: Dive into Kea’s underwater world and explore nearby reefs and historical shipwrecks.
Chora & Castle: Climb up to the Cycladic Chora and explore the ruins of a Venetian castle with sweeping sea views.
Psili Ammos Beach: Swim in shallow turquoise waters on one of Greece’s best-rated beaches.
Island Trails: Hike between villages and discover secluded chapels, stone bridges and windmills.
Taste Serifos: Try local specialties like chickpea fritters, caper salad and traditional sausage in rustic tavernas.
Kleftiko: Swim through the stunning volcanic rock arches and sea caves in this iconic natural wonder.
Sarakiniko Beach: Walk on the island’s lunar landscape — white volcanic rock meets deep blue sea.
Ancient Theater: Visit the well-preserved ancient theater of Milos with views over the bay.
Plaka & Klima: Stroll through the romantic capital and visit the colorful seaside houses of Klima during sunset.
Cyclades Sailing Gallery
Frequently Asked Questions
Yes. All routes are flexible and can be customized to suit your preferences, weather conditions, and available time.
Absolutely. The Saronic Gulf is known for calm waters, short distances, and safe anchorages – ideal for first-time sailors.
Of course. We can help you arrange water sports, guided tours, or land-based experiences upon request.
Yes, children can absolutely join this sailing trip. While the Cyclades may include longer sailing legs and livelier conditions compared to other regions, we carefully plan the route based on your group and the weather. Many families enjoy this route by adjusting the daily distances and anchoring in safe, family-friendly bays.
Ready to Set Sail?
Sail beyond the postcards and dive into the essence of the Cyclades — where each island reveals a different side of Greece.
Whether you're anchoring beneath white cliffs, strolling through untouched villages, or enjoying a quiet sunset at sea, this journey offers something more than just a vacation.
Let the rhythm of the Aegean guide you, and begin a sailing escape that’s truly yours.