Special 8-Day Santorini to Santorini Yacht Charter Itinerary

Route Overview

Arrival in Santorini

Santorini is the embarkation point and the main reason to choose this itinerary. The island is the rim of a collapsed volcano, with Fira, Oia and Imerovigli hanging along the caldera cliffs. The Bronze Age town of Akrotiri, buried by ash after a huge eruption in the 17th century BC, is one of the most important archaeological sites in the Aegean.

We recommend arriving at least one day before boarding. Many of our clients book a caldera-view hotel first, then join the yacht at Vlychada marina on the south coast once they’ve had time to enjoy the viewpoints, wines and restaurants ashore.

Highlights

• Caldera-view stay in Fira, Oia or Imerovigli
• Optional visit to Akrotiri and the black- or red-sand beaches
• Evening welcome and briefing with your captain and crew at Vlychada

Day 1 – Santorini to Folegandros

Leaving Santorini, the yacht heads west to Folegandros, where the pace drops immediately. The island stayed off the radar for years thanks to its dry climate, strong winds and tiny population, and it still feels a long way from cruise-ship Greece.

Karavostasi and Ormos Vathi are the main anchorages. From there, a short ride takes you up to Chora, one of the most dramatic cliffside villages in the Cyclades, with an old Kastro and linked squares full of small tavernas.

Highlights

• Wandering the clifftop Chora and Kastro quarter
• Sunset walk up to Panagia church above the village
• Swimming and snorkelling at coves like Agali, Vorina or Katergo

Day 2 – Folegandros – Kimolos – Milos

From Folegandros the route continues north towards Kimolos, Polyaigos and Milos – a classic west Cyclades coastal day.

Kimolos offers a quiet, local feel with a handful of anchorages and low-key beaches. Nearby Polyaigos is essentially uninhabited and protected; monk seals still use its sea caves to raise their pups, which is one reason we see it as a “treat it gently” stop rather than a party bay.

Milos then delivers the drama: the white, lunar rock of Sarakiniko, the sea caves and arches of Kleftiko, and the colourful fishermen’s syrmata boathouses at Klima right on the waterline. It’s one of those coastlines where a private yacht makes all the difference.

Highlights

• Quiet anchorages and wild coastline around Kimolos and Polyaigos
• Cruising past Sarakiniko’s white rock and turquoise water
• Time at Kleftiko or Klima for caves, cliffs and syrmata houses

Day 3 – Milos to Sifnos

From Milos, the yacht heads north-east to Sifnos, which we often recommend to guests who care about food as much as beaches.

Sifnos has a long tradition of pottery and slow-cooked dishes like revithada (baked chickpeas) and mastelo (lamb in wine in clay pots). Bays such as Vathi, Faros and Platis Gialos work beautifully as lunch and swim stops, with tavernas right on the sand. For the night, Kamares makes a convenient base with easy access up to Kastro and the Church of the Seven Martyrs on its rock.

Highlights

• Swim and lunch stops in Vathi, Faros or Platis Gialos
• Dinner trying traditional revithada, mastelo and local sweets
• Evening visit to Kastro and the Church of the Seven Martyrs

Day 4 – Sifnos – Antiparos – Paros

Today the route bends back towards central Cyclades via Antiparos and Paros.

Antiparos is all about clear water and relaxed bays, ideal for a long swim, snorkel, and toys session off the yacht. The Antiparos Cave, dropping over 80 metres underground with inscriptions going back centuries, is an option if you want an inland detour.

From there, it’s a short hop to Paros, now one of the most in-demand Cyclades islands. In Parikia and Naoussa, you will find a nice mix of fishing boats and chapels with stylish bars and restaurants, so the evening can be as low-key or as polished as you like.

Highlights

Day 5 – Paros to Naxos

From Paros, a short passage east takes you to Naxos, often described as the breadbasket of the Cyclades. It’s the largest and one of the greenest islands in the group, with fields, citrus groves, vineyards and olive trees still very much part of everyday life.

On the coast, Naxos is about big beaches and water sports. Agios Prokopios, Plaka and Agios Georgios offer long runs of sand and shallow, clear water. Above the harbour, the Venetian Kastro and the marble gate of the Portara give the island its signature outline.

Highlights

• Beach time on the west coast with long sandy shorelines
• Early evening walk up to the Portara for views over Naxos Town
• Tasting Naxian potatoes, local cheeses and possibly kitron liqueur

Day 6 – Naxos – Koufonisia – Schoinousa

Day 6 moves into the Small Cyclades, which are almost purpose-built for yachts: short hops, turquoise water, very little development.

First is Koufonisia (Ano and Kato). Ano Koufonisi has a small port village and a chain of beaches like Pori, Italida and Fanos. The coast is full of sea caves and natural pools, and crews know exactly where to tuck in for the best swimming and photos. Kato Koufonisi is uninhabited and perfect for a quiet anchorage and long, lazy swims.

Later, the yacht continues to Schinousa, a tiny island south of Naxos with a slow, easy rhythm. Most beaches are an easy walk or short tender ride from Chora, and the evening usually distils down to: swim, shower, taverna, stars.

Highlights

• Toys out in the turquoise coves of Koufonisia
• Swimming and tender runs to sea caves and rock pools
• Quiet evening on Schinousa with a simple village taverna dinner

Day 7 – Koufonisia to Ios

From Schinousa, the captain sets course towards Ios. Ios has a dual identity: famous for its nightlife, but also home to some of the best beaches in the Cyclades at Mylopotas and Manganari. Up on the hill, Ios Chora is a maze of steps, small squares and churches; higher still, Panagia Gremiotissa and the supposed Tomb of Homer both offer wide views over the Aegean.

This is usually a “choose your own energy” stop: some guests lean into the cocktail bars; others keep it to beaches and viewpoints.

Highlights

Beach and toys at Mylopotas or Manganari

Exploring Ios Chora’s lanes, churches and viewpoints

Optional evening climb to Gremiotissa or Homer’s Tomb for sunset

The final day is a short run back to Santorini, which keeps departure day calm. There’s usually time for a last swim and an unhurried breakfast or lunch at anchor before the yacht returns to Vlychada marina for disembarkation.

We generally suggest planning at least one more night ashore – either back on the caldera or in Athens – rather than aiming for tight long-haul connections the same day.

Highlights

• Final open-deck sail towards the Santorini cliffs
• Last swim and relaxed brunch on board
• Farewell to the crew and onward travel or extra nights on Santorini