A sailing holiday around Santorini and the surrounding Cyclades islands would make a fantastic trip. I'd suggest combining beautiful anchorages, swimming and snorkelling, traditional Greek villages, archaeological sites, lovely tavernas and a little island hopping.
My recommendation would be a circular itinerary starting and finishing in Santorini, with a mixture of sailing days and time ashore. I'd aim for a relaxed pace rather than trying to visit too many islands.
Suggested route: Santorini → Nea Kameni → Thirasia → Ios → Sikinos → Folegandros → Anafi → Santorini.
This gives you a lovely mixture of volcanic scenery, quieter Greek islands and traditional villages.
The day-by-day programme
Day 1 – Santorini and the volcanic caldera
- Collect the yacht at Vlychada Marina.
- Sail along the spectacular volcanic coastline.
- Visit the volcanic islands of Nea Kameni and Palea Kameni, with a swim where conditions permit.
- Enjoy dinner ashore overlooking the caldera, perhaps in Fira or Imerovigli.
Day 2 – Thirasia
- Short sail to the quieter island of Thirasia.
- Explore Manolas village, with its traditional whitewashed houses.
- Walk up to the village viewpoints.
- Lunch at a traditional Greek taverna.
- Afternoon swimming and snorkelling in a sheltered bay.
Day 3 – Ios
- Sail to Ios and anchor or berth at Gialos.
- Visit Chora, a beautiful traditional village with winding streets and windmills.
- Explore the shops and cafés.
- Visit Mylopotas Beach for swimming and watersports.
- Dinner in Chora overlooking the island.
Day 4 – Sikinos
- Sail to this quieter, less-developed island.
- Visit the beautiful hilltop village of Kastro.
- Explore the traditional lanes and churches.
- Enjoy a leisurely lunch in a family-run taverna.
- Spend the afternoon swimming in clear water.
Day 5 – Folegandros
- Sail to Folegandros.
- Visit Chora, one of the prettiest villages in the Cyclades.
- Walk up to the Church of Panagia for spectacular views.
- Enjoy a leisurely lunch and browse the boutiques.
- Spend the afternoon at a beach such as Agali, subject to anchorage and weather conditions.
Day 6 – Anafi
- Sail towards Anafi, a beautiful and relatively unspoilt island east of Santorini.
- Explore Chora and its traditional Greek architecture.
- Visit the impressive Kalamos rock formation and Monastery of Zoodochos Pigi.
- Enjoy a final island lunch and a relaxing swim.
- Overnight in a suitable sheltered anchorage or harbour.
Day 7 – Return to Santorini
- Sail back to Santorini.
- Enjoy a final swim and lunch on board.
- Return to Vlychada Marina.
- Finish with a special farewell dinner overlooking the caldera.
When to go
My preference would be June or September:
- June: warm weather, lovely swimming conditions and generally less crowded.
- September: warm sea temperatures, a slightly quieter atmosphere and beautiful evenings.
- July/August: busier and potentially much windier, particularly because of the Meltemi.
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