Santorini Itineraries: Day Charters and Multi-Day Routes
Santorini’s caldera is the centrepiece, but the surrounding islands offer variety and contrast that turn a short charter into a genuine Cycladic adventure. The itineraries below cover different ground and can be combined into a 7-day or longer voyage.
Day Charter Routes
Caldera and Volcano Day Charter
Depart from Vlychada Marina or Athinios Port and cruise into the caldera. Anchor beneath the cliffs of Fira and take the tender ashore (or ride the cable car) for a morning in town. Cruise to Nea Kameni for a hike to the volcanic crater and a swim in the hot springs. Continue to Thirassia for a quiet lunch at a harbourside taverna. Return to your caldera anchorage for a sunset dinner on the aft deck beneath Oia. Total: roughly 15 nm, 7–9 hours.
South Coast Explorer Day Charter
Cruise south from the caldera to Red Beach, anchoring off the dramatic red volcanic cliffs. Swim and snorkel in the cove. Continue to White Beach (accessible only by boat) and then east to Perissa, a long stretch of black volcanic sand. Your chef prepares lunch on the aft deck. Cruise around to Kamari for a late swim, then return to the caldera for sunset. Total: roughly 20 nm, 7–8 hours.
3-Day Santorini Yacht Charter Itinerary: Santorini, Ios and Sikinos
Day 1: Santorini Caldera, Nea Kameni and Akrotiri
Board at Vlychada Marina. Cruise into the caldera and anchor beneath Imerovigli. Take a tender to Nea Kameni for a volcanic-crater hike and hot-springs swim. Return to the yacht for lunch, then cruise to Akrotiri for a guided tour of the Bronze Age site. In the late afternoon, anchor off Red Beach for a swim beneath the towering red cliffs. Return to the caldera for a sunset dinner on the aft deck – Santorini fava, grilled octopus, cherry tomatoes, and a glass of local Assyrtiko.
Day 2: Ios
Cruise north to Ios, 20 nautical miles (roughly one hour). Anchor off Manganari Beach on the south coast – a long crescent of golden sand in a sheltered bay, one of the finest beaches in the Cyclades. Swim, snorkel and paddleboard in turquoise shallows. After lunch onboard, take the tender to the harbour and walk (or take a bus) up to the hilltop Hora – a tumble of white lanes, blue-domed churches and rooftop terraces. For the curious, Homer’s Tomb on the northern tip is a small archaeological site said to mark the poet’s final resting place. Dinner onboard or in the Hora’s atmospheric lanes.
Day 3: Sikinos and Return to Santorini
Cruise west to Sikinos, roughly 12 nautical miles from Ios. Sikinos is one of the least visited islands in the Cyclades – tiny, quiet and deeply authentic. Anchor in the small harbour of Alopronia and walk to the clifftop Chora, where life moves at a pace that feels unchanged for decades. Visit the Episkopi Monastery, built on the ruins of a Roman temple, with views across the sea to Folegandros and Ios. After a peaceful morning, cruise back to Santorini (20 nm, one hour), arriving for a farewell caldera sunset.
4-Day Santorini Yacht Charter Itinerary: South Through the Cyclades to Milos
Day 1: Santorini and Thirassia
Board at Vlychada Marina. Spend the morning exploring the caldera: hot springs at Nea Kameni, Akrotiri archaeological site, and a swim at Red Beach. After lunch onboard, cruise to Thirassia on the opposite rim of the caldera. This quiet island has a handful of houses, a tiny harbour, and the feeling of Santorini before the tourists arrived. Dine at a caldera-view taverna in the village of Manolas, then anchor for the night in Thirassia’s sheltered bay.
Day 2: Folegandros
Depart west for Folegandros, roughly 30 nautical miles (about 90 minutes). Anchor off Katergo Beach – accessible only by boat, a strip of sand and turquoise water beneath sheer cliffs. Swim and snorkel in solitude. In the afternoon, go ashore at Karavostasis harbour and walk up to the clifftop Chora – whitewashed houses, bougainvillea-draped lanes, and the Church of Panagia perched above a 300-metre drop. The sunset from the churchyard is one of the finest in the Cyclades. Dinner in one of the Chora’s intimate tavernas.
Day 3: Kimolos
Cruise north-west to Kimolos, roughly 35 nautical miles (about two hours). Kimolos is Milos’s quiet neighbour – a volcanic island with just 900 residents, excellent beaches, and a charming Chora with a Venetian castle at its centre. Anchor off Prassa Beach for a morning swim in crystal water, then explore the Chora’s narrow lanes. The island is known for its ladenia – a traditional flatbread topped with tomatoes, onions and olive oil. Cruise around to Bonatsa Beach on the south coast for an afternoon swim. Overnight in Kimolos harbour.
Day 4: Milos
A short 3-nautical-mile crossing brings you to Milos. Head south to Kleftiko – the island’s unmissable natural wonder: white rock arches, sea caves and turquoise pools once used by pirates. Snorkel through stone archways and explore hidden chambers. After lunch on the aft deck, cruise to Sarakiniko – the lunar white volcanic landscape – for a late swim. End the charter in Adamas harbour, or continue to Plaka, Milos’s clifftop capital, for a farewell sunset with views stretching across the Aegean.
Guests looking for a longer voyage can combine the 3-day Santorini–Ios–Sikinos route with the 4-day westbound route (Thirassia, Folegandros, Kimolos, Milos) for a comprehensive 7-day charter covering the volcanic southern Cyclades without repeating a single stop.
