Aegean Islands Odyssey
Greece · 8 days · May – October · Max 12 guests
Overview
The trip, in one breath.
Eight days across the Cyclades at the pace the islands were designed for: slow. You'll base yourselves in Santorini's cliff villages, island-hop to Naxos for empty beaches and mountain towns, then sail to a lesser-known island we keep deliberately quiet. Private catamaran crossings mean you never queue for a ferry.
Highlights
- Private catamaran day sail around the caldera with a sunset swim
- Two nights in a whitewashed cave suite carved into the cliff
- Guided walk through Naxos' marble mountain villages
- Taverna dinner cooked by the third-generation family who runs it
- Small group of twelve — never more
Day by day
The itinerary.
Day 1
Arrival in Santorini
Airport meet-and-greet, private transfer to your cliff-side suite and a welcome dinner with views over the caldera.
Day 2
The Caldera by Catamaran
A full day on the water — hot springs, a swim in the middle of the bay, and a slow sail into the sunset.
Day 3
Fira to Oia on Foot
The famous cliff path at first light, before the day's heat, ending with long lunch in Oia's narrow lanes.
Day 4
Ferry to Naxos
Private transfer to Naxos, then an afternoon on the marble old town's cafe terraces.
Day 5
Mountain Villages & Beaches
A drive into the island's heart: hilltop villages, a monastery lunch, and a deserted southern beach for the evening.
Day 6
The Secret Island
A short sail to our quiet favourite — think 1970s Greece before it was discovered.
Day 7
At Leisure
A free day: swim, read, or join an optional sailing masterclass. Sunset dinner at the family taverna.
Day 8
Departure
Leisurely breakfast and a private transfer back to the airport, memories packed.
Included
What the price covers.
- All accommodation (4-star & boutique, en-suite)
- Breakfast daily, 4 dinners & 2 lunches
- Private catamaran sail & all island transfers
- Licensed local guides on all walking days
- Airport meet-and-greet on arrival
- 24/7 in-trip support from our concierge team
Not included
The honest list.
- International flights
- Travel insurance (we can arrange it)
- Optional activities & personal spending
Insurance is required on all journeys — we can arrange it through our partner in under five minutes.