Description
Private Skippered 14-Day Athens to Santorini & Cyclades Grand Tour aboard Astrea 42 Maestro
Two weeks, countless shades of blue. Depart Athens with a professional skipper and trace a sweeping arc through the Cyclades: hushed coves, classical temples, sculpted villages and sunset anchorages you will talk about for years. This extended itinerary layers culture and scenery with ample time to swim, wander and linger over dinners where the sea is always in view. It is the ultimate slow-sailing exploration of the Aegean.
About Our Service in Athens and the Wider Cyclades
We cast off from a premium marina in Athens designed for smooth departures and easy provisioning. With the city fading astern, we follow a thoughtfully sequenced route that balances open-water reaches with relaxed daily distances. Over fourteen days we call at Sounio, Kea, Loutra on Kythnos, Syros, Mykonos, Delos, Paros, Ios, Sikinos, Thira (Santorini), Folegandros, Kimolos, Sifnos, Serifos, Merichas on Kythnos, Poros and Aegina before returning to Athens. The skipper adapts the cadence to your preferences and the breeze, keeping the experience personal and unhurried.
Day 1 - Athens Embarkation
Arrive late afternoon, meet your crew and settle into bright, welcoming cabins. A concise safety briefing is followed by sunset cocktails and a relaxed dinner onboard or at a nearby taverna. The city lights glitter as anticipation builds.
Day 2 - Athens → Sounio → Kea (Vourkari) - ~40 NM
We trace Attica’s coast to Cape Sounio and the cliff-top Temple of Poseidon, a stirring sight for sailors. By evening we are moored in Kea’s Vourkari, a charming anchorage with cozy tavernas and a gentle harbor scene.
Day 3 - Kea → Loutra, Kythnos - ~20 NM
Loutra’s thermals invite a soak after a swim in translucent water. Explore Chora’s lanes, then return for a mellow sunset afloat. Dinner ashore features Greek meze and delicate island wines.
Day 4 - Kythnos → Syros → Mykonos - ~40 NM
We pause in Syros to admire Ermoupoli’s neoclassical grace before a short hop to Mykonos. Wander Little Venice and view the windmills, then choose between the island’s vibrant dining scene or a quiet evening under the stars in Ornos Bay.
Day 5 - Mykonos → Delos → Paros - ~25 NM
A morning visit to sacred Delos connects you to antiquity among marble columns and myth. By afternoon we are in Paros, splitting time between sandy beaches, boutique-lined alleys and a waterfront dinner that glows pink with sunset.
Day 6 - Paros → Ios - ~25 NM
Ios greets us with gold-rimmed bays ideal for paddleboarding and long swims. Stroll Chora’s whitewashed lanes and blue-domed churches before a tranquil night on the hook.
Day 7 - Ios → Sikinos → Thira (Santorini) - ~20 NM
We anchor off quiet Sikinos for a swim, then time our approach to Santorini for a caldera sunset. Explore Fira and Oia’s cliffside paths and savor world-class cuisine with views you’ll remember forever.
Day 8 - Santorini → Folegandros - ~30 NM
Folegandros is dramatic and serene. Swim in luminous water, then climb to Chora for a panorama where sea and sky seem to meet. Dinner is simple, local and perfect.
Day 9 - Folegandros → Kimolos → Sifnos - ~20 NM
We pause at Kimolos for a swim in a quiet bay before continuing to Sifnos for an evening exploring Apollonia and Kastro. Expect artisan shops, elegant lanes and exquisite island cooking.
Day 10 - Sifnos → Serifos - ~20 NM
Serifos offers rugged beauty and crowd-free beaches. After time in the water, we ascend to Chora for sunset views and dinner in a tavern where the night sky feels close.
Day 11 - Serifos → Merichas, Kythnos - ~15 NM
A relaxed day in Merichas brings long swims, paddleboarding and beach time. Evenings are quiet, marked by the sound of water against the hull and a dome of stars overhead.
Day 12 - Kythnos → Poros - ~45 NM
The scenery shifts to Poros’ pine-draped shores and neoclassical waterfront. Kayak in protected bays, browse harbor boutiques and enjoy an elevated dinner with harbor views.
Day 13 - Poros → Aegina - ~30 NM
Aegina’s pistachio groves and the Temple of Aphaia invite exploration. Swim at a sandy beach, taste local sweets and soak in the island’s gentle pace on your final island evening.
Day 14 - Aegina → Athens - ~25 NM
We glide back toward Athens, pausing for a last swim in a quiet cove. By late afternoon we are alongside for a smooth disembarkation. Your photos will be beautiful, but the true souvenir is the way this route re-sets your sense of time.
About Our Yacht – Astrea 42 Maestro
Purpose-built for Mediterranean cruising, the Astrea 42 Maestro balances sailing capability with abundant space. Five cabins comfortably host up to ten guests, with large windows, clever storage and excellent airflow. The saloon and cockpit share a single-level layout that keeps everyone connected, whether prepping lunch, lounging with a book or lingering over dinner. Forward sunbeds and a wide foredeck feel like your private beach club; aft, a stable swim platform simplifies dips and water-toy launches.
With a responsive rig and modern electronics, passages are smooth and engaging. At anchor, refined finishes and panoramic glazing make even quiet moments memorable. Coupled with your experienced skipper and optional concierge extras such as provisioning, transfers and early check-in, the yacht becomes the ideal home base for a long, luxurious Aegean odyssey.
If you have always dreamed of a deeper dive into the Cyclades, this two-week private charter is the way to do it: iconic sites, secret coves, gracious villages and time enough to savor them all. Secure your dates and let Athens be your gateway to a grand, unhurried adventure at sea.
