Cyclades Islands Sailing Itinerary from Lavrion - 7 Day Island Hopping through Kea, Mykonos, Paros, Serifos and Kythnos
31 October 2026 - 7 November 2026
Cyclades Islands, GR
7 days trip
10 places avaliable
Sailboat
Price may vary depending on the cruise date.
Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
A 7-day sailing holiday through the western and central Cyclades, navigating between Athens and five Greek islands with Aegean winds, clear anchorages and traditional island harbours.
The Cyclades form the most iconic sailing destination in Greece and one of the most consistently rewarding in the entire Mediterranean. The 39 islands of the archipelago are distributed across a compact area of Aegean water, close enough to each other to allow daily island hopping while remaining distinct enough in character that each stop feels genuinely different. The combination of reliable winds, clear turquoise water, whitewashed villages and ancient history concentrated in a small sailing area is difficult to find anywhere else in Europe.
This 7 day sailing itinerary departs from Lavrio, on the eastern Attica coast approximately 40 minutes by car from Athens International Airport, and develops eastward and southward through five of the most accessible and visually striking islands in the western Cyclades: Kea, Mykonos, Paros, Serifos and Kythnos. The route is designed to balance sailing distances with time ashore, alternating longer passages with shorter day sails and overnight stops in harbours and bays that each offer a different atmosphere.
The defining natural feature of Cyclades sailing is the Meltemi, a persistent northerly wind that builds from early July through mid-August and can reach force 7 or above in exposed passages, particularly around Mykonos and in the open channels between islands. In the months before and after the main Meltemi season, from early June to late June and from September onward, conditions are considerably more moderate and suited to a wider range of sailing experience levels. Understanding the Meltemi is part of sailing the Cyclades, and navigating with it rather than against it shapes both the daily routing and the overall experience of the week.
The route passes through some of the most photographed and historically layered places in Greece. Mykonos is one of the most internationally recognized islands in the Mediterranean, with a cosmopolitan harbour, a legendary nightlife and the nearby sacred island of Delos just a short sail offshore. Paros offers a contrast with its traditional Cycladic architecture, quieter atmosphere and excellent anchorage options on multiple sides of the island. Serifos and Kythnos represent a different character again, less visited, more rugged and anchored in the everyday life of small Aegean island communities. Kea, the closest island to the mainland, rounds out a circuit that covers a wide range of what makes the Cyclades such a compelling sailing destination.
Itinerary
Day1
Lavrion, Boarding and First Sail to Kea
Boarding takes place at Lavrio Marina on the eastern coast of Attica. The morning and early afternoon are useful for provisioning from the shops near the port before the week begins. Departure in the early evening allows the boat to reach Koundouros Bay on the southwest coast of Kea before dark, a well-protected cove surrounded by low hills and clear water well suited to a first night at anchor. Dinner is served onboard with the first views of the Aegean under the evening sky.
Day2
Kea to Mykonos
After breakfast and a morning swim in the clear water of Koundouros, the boat sets sail for Mykonos on the longest passage of the week. The northerly wind typically fills in through the morning, creating beam reach conditions for much of the crossing and rewarding sailors who time their departure well. The approach to Mykonos in the late afternoon reveals one of the most recognizable harbours in the Aegean, with the iconic windmills on the hill above the waterfront and the maze of whitewashed streets rising behind the quay. The evening is free to explore Mykonos Town, its restaurants, waterfront cafés and the animated nightlife for which the island is internationally known.
Day3
Mykonos and Delos
A full day in the Mykonos area with the option of a morning sail to the nearby island of Delos, one of the most significant archaeological sites in the ancient Greek world and the mythological birthplace of Apollo and Artemis. The ruins of the ancient city, including the famous Terrace of the Lions, are remarkably well preserved and the island is visited only by day since no overnight stays are permitted. Alternatively, the day can be spent exploring the southern coastline of Mykonos by sail, with several sheltered bays and beaches accessible only from the water, or simply relaxing ashore in Mykonos Town.
Day4
Delos to Paros
Morning departure toward Paros, a shorter sail that leaves time for flexibility on route. Depending on wind and sea state, the skipper may suggest a brief stop at Rhenia, a small uninhabited islet just west of Delos with free anchorage and clean water well suited to a morning swim before the final approach to Paros. The arrival harbour is selected based on conditions: Naoussa in the north is lively and well-protected, Paroikia on the western side offers easy access to the main town, and Antiparos just offshore provides a quieter option with golden beaches and a relaxed island atmosphere.
Day5
Paros to Serifos
An early departure is recommended for this longer westward passage, which leads away from the busier central Cyclades and toward the more remote western islands. Serifos is one of the least developed islands in the archipelago, with a dramatic hilltop Chora visible from the sea long before the boat enters the harbor at Livadi. The port is small and fills quickly in high season, making an early arrival worthwhile. The evening reward is dinner in the tavernas below the hill or a walk up to the upper town for panoramic views over the Aegean at sunset.
Day6
Serifos to Kythnos
Navigation continues northward toward Kythnos, with the route following either the east or west coast of Serifos depending on wind direction. The channel between the two islands is one of the more demanding sections of the itinerary in strong northerly conditions, and the skipper may choose to sail further west before tacking northeast to avoid the most accelerated wind in the strait. Kythnos offers two distinct stop options: the fishing harbour of Merichas with its waterfront tavernas and easy provisioning, and the bay of Kolona, a remarkable natural sandbar connecting two sections of coastline that creates a double-sided beach accessible by anchor. Both are worth time. Overnight in Merichas or at anchor in Kolona Bay.
Day7
Kythnos to Lavrio and Disembarkation
The final navigation heads northwest back toward the Attica coast. Time is reserved for a last swim at Kolona Bay before departure, and the route passes below Cape Sounion, where the Temple of Poseidon stands on the headland above the sea, visible from the water in clear conditions. A brief anchoring stop in the bay below the temple is a natural close to a week in the Aegean before the final approach to Lavrio Marina in the afternoon. Guests spend the last night onboard and disembarkation takes place the following morning by 09:00.
Important Note
This itinerary may vary depending on weather conditions, currents and marine activity. Daily navigation planning is adjusted by the skipper to ensure safety and the best possible sailing experience throughout the week.
Cruise price details
Entire yacht price
€ 2900
€ 2175
Book the entire yacht for a private trip
Included in the price
Entire boat rental
Tender
Mooring at the base
Complete equipment of the boat
Outboard engine
Bed linen, towels and blankets, one set per cabin per week
The Dufour 430 Grand Large is a 43-foot monohull designed by Umberto Felci that navigates the balance between genuine sailing performance and onboard comfort without sacrificing either. Wide hull windows, large overhead skylights and a forward galley arrangement that opens the saloon make the interior feel considerably more spacious than the boat's length suggests.
The Dufour 430 Grand Large was nominated for Best Boats 2020 in the cruising monohull category, a recognition that reflects how successfully the design manages the transition between a hull shaped for performance and an interior built for comfortable living over multiple days at sea. Naval architect Umberto Felci, the same designer behind the Dufour Catamaran 48, carried both the hull and interior concept, producing a boat with high sides, a wide stern and a full bow that gives the 430 its immediately recognizable profile in a marina.
On deck, the cockpit is well organized for both sailing and socializing, with twin helms, a central cockpit table and enough room to move freely when the full group is onboard. Side decks are wide and passage forward past the lower shrouds is straightforward, which makes day-to-day boat handling less demanding than on comparable-sized monohulls. The twin-wheel setup gives clear visibility over the stern and contributes to the direct, responsive feel the 430 delivers under sail in conditions ranging from light thermal breezes to stronger coastal winds.
Below deck, the interior is the boat's strongest argument. The three-cabin version uses a forward galley arrangement that positions the cooking and preparation area against the forward bulkhead, separating it from the main seating area and creating a saloon that reviewers consistently describe as feeling closer to a 48-foot vessel. Natural light enters through two forward portlights, two panoramic side windows and overhead skylights, keeping the interior bright throughout the day. The master cabin forward features an island queen berth that benefits from the full beam of the bow, while the two aft cabins offer above-average sleeping width at 1.68 meters, each with comfortable access and headroom for a cruising week.
The four-cabin charter version replaces the forward galley with a linear galley along the starboard side to accommodate a fourth cabin forward. Both configurations share the same quality of light, ventilation and general finish below deck.
The exact configuration will be confirmed before departure while maintaining the same standard of onboard comfort.
What to pack for a sailing holiday?
Pack smart for your yacht charter: choose a soft bag instead of a hard suitcase, bring lightweight layers, reef-safe sunscreen, and non-slip shoes for onboard use. A couple of swimsuits and motion sickness remedies can also make a big difference. Each boat has limited storage, so pack light but wisely! Need help building the perfect list? Read our full guide: What to pack in a suitcase for a yacht charter
What’s a Typical Day Like on a Yacht Charter?
Start your day with a swim in a quiet bay, sail to hidden beaches or seaside villages, and enjoy a slow lunch on deck. Afternoons mean snorkeling, sunbathing, or exploring ashore. As the sun sets, your boat anchors in a scenic cove or near a harbor, ready for a relaxed dinner and a night under the stars. Curious about the full experience? Discover more in our guide: What’s a typical day like on a sailing holiday?
Who Handles Cooking and Cleaning on a Yacht Charter?
On skipper-only charters, guests usually share cooking and cleaning duties think salads, pasta, and good teamwork. If there's a hostess, light meals and tidying are included, but it's still a casual, collaborative vibe. On fully crewed yachts, you’ll enjoy full service with a chef and crew managing everything. Want to know what’s included in your setup? Read the full guide: Who takes care of cooking and cleaning on a sailing charter?
What Happens in Case of Bad Weather During a Sailing Holiday?
Summer sailing holidays rarely face major weather issues but when the sea gets rough, skippers adjust the route for your safety. Expect protected bays, marina stops, or a change in plan. These moments often lead to unexpected gems: local towns to explore, time to relax on board, or cozy dinners ashore. Curious about how crews handle these changes? Read the full FAQ: What to do in case of adverse weather conditions or changes to the itinerary
Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
