Cyclades Island Hopping Sailing Itinerary from Paros
24 October 2026 - 31 October 2026
Paros, GR
7 days trip
12 places avaliable
Catamaran
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 relaxed sailing journey through the Small Cyclades and southern Aegean islands, combining sheltered bays, traditional villages, swim stops and authentic Greek island atmosphere.
Starting from Paros in the heart of the Cyclades, this sailing itinerary explores a combination of well known islands and quieter anchorages connected by short to medium navigation legs. The route is designed for balanced cruising, alternating open sea passages with protected bays, traditional harbors and relaxed evenings ashore.
The navigation follows the typical rhythm of Cycladic sailing, shaped by the Meltemi winds, whitewashed villages and clear Aegean waters. Guests experience a mix of lively island ports, remote coves accessible mainly by sea and authentic fishing villages where local tavernas remain part of daily island life.
Daily life onboard revolves around outdoor living, with breakfasts at anchor, swim stops in turquoise bays and evening moorings in small marinas or natural harbors. Navigation distances remain comfortable for a one week cruise while still allowing time to enjoy the atmosphere of each island.
The itinerary is suitable for travelers looking for a sailing focused holiday with a balance between exploration, relaxation and traditional Cycladic scenery.
Itinerary
Day1
Paros Embarkation and Navigation to Antiparos
Arrival in Paros and embarkation in the afternoon. After boarding, guests settle into the cabins and receive a short onboard briefing before departure. Depending on weather conditions and arrival time, the first navigation heads toward nearby Antiparos. The short sail offers an easy introduction to the Cyclades, passing along rocky coastlines and small uninhabited islets. Arrival in a protected bay or harbor in Antiparos for the evening. Time for a first swim stop or a relaxed dinner ashore among the narrow whitewashed streets and waterfront tavernas.
Day2
Antiparos to Despotiko and Koufonisia
Morning departure toward the uninhabited island of Despotiko, known for its transparent waters and quiet anchorages. A swim stop allows time for snorkeling and relaxing onboard before continuing east through the Small Cyclades. The afternoon navigation reaches Koufonisia, one of the smallest inhabited islands of the archipelago. The harbor atmosphere remains relaxed, with small fishing boats, waterfront cafés and walking paths connecting sandy beaches and rocky coves. Overnight in port or at anchor depending on conditions.
Day3
Koufonisia to Schinoussa and Iraklia
After breakfast, a short sail leads toward Schinoussa, a quieter island with sheltered bays and a slower rhythm of life. Time for swimming and paddle activities before continuing toward Iraklia. Iraklia offers a more traditional Cycladic atmosphere with low tourism development, peaceful anchorages and hiking paths overlooking the Aegean Sea. The evening is spent in a small harbor or natural bay with dinner onboard or ashore in a local taverna.
Day4
Iraklia to Ios
A longer navigation day begins with a crossing toward Ios. The route passes through open Aegean waters where wind conditions often create more active sailing opportunities. Along the southern coast of Ios, several bays provide optional swim stops before arriving at the island’s main harbor. Ios combines traditional Cycladic architecture with a lively waterfront atmosphere. Guests may explore the hilltop Chora, known for its narrow alleys, sea views and local restaurants.
Day5
Ios to Folegandros
Departure toward Folegandros, one of the most scenic islands in the southern Cyclades. The approach by sea reveals steep cliffs rising directly above the water and small isolated coves accessible only by boat. After anchoring for swimming in a protected bay, the route continues toward the island harbor. In the evening, guests can visit the upper town of Chora, perched above the cliffs and connected by winding pedestrian lanes and small squares.
Day6
Folegandros to Sifnos
Morning navigation north toward Sifnos, an island known for traditional villages, terraced hillsides and a strong culinary heritage. The sailing route includes possible swim stops along the southern coast depending on sea conditions. Arrival in a harbor or bay near Apollonia or Kamares. The island atmosphere remains more relaxed compared to larger Cycladic destinations, with opportunities to explore local pottery shops, walking trails and waterfront tavernas.
Day7
Sifnos to Paros and Disembarkation
Short morning navigation back to Paros. Breakfast onboard and final moments to enjoy the harbor atmosphere before check-out and disembarkation around late morning depending on marina procedures and weather conditions.
Important Note
This itinerary may vary depending on weather conditions, currents and marine activity. Dive sites and schedule are adjusted daily by the team to ensure safety and the best possible underwater experience.
Designed for comfortable coastal and offshore cruising, the Lagoon 42 combines spacious outdoor living areas with an easy and balanced sailing experience. Its open layout, stable navigation and bright interiors make it well suited for couples, families and small groups looking for relaxed sailing with modern onboard comfort.
The Lagoon 42 is a modern cruising catamaran built to balance comfort, practicality and smooth sailing performance. The wide beam creates generous living spaces both inside and on deck, allowing guests to move easily between the cockpit, saloon and foredeck lounge areas. Large panoramic windows bring natural light into the interior while maintaining continuous sea views throughout the day.
The cockpit is designed as the social center of the boat, with a large dining table, shaded seating area and direct connection to the saloon. This open-plan layout creates a relaxed onboard atmosphere, ideal for shared meals, sunset aperitifs and quiet evenings at anchor. Forward, the trampoline and cushioned lounge spaces offer additional areas to relax while sailing or during swim stops.
The elevated helm station provides good visibility and keeps sailing operations connected to the social areas without isolating the skipper from the group. The sail plan and maneuvering systems are designed for smooth handling, making the Lagoon 42 comfortable both under sail and during marina maneuvers. The catamaran’s stable platform also reduces motion while anchored or navigating in moderate sea conditions.
Accommodation layouts may vary between owner and charter versions, typically offering three or four double cabins with private bathrooms. Cabins are designed with practical storage, good ventilation and large hull windows that create a bright and comfortable atmosphere for longer stays onboard.
The Lagoon 42 is appreciated for its balance between sailing efficiency and onboard livability, making it suitable for island hopping itineraries, family sailing holidays and multi-day cruises in destinations such as the Mediterranean, Caribbean and tropical archipelagos.
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.
