Athens to Santorini: Greek Island Hopping
Eight days island-hopping through the Cyclades — Athens, Syros, Mykonos and the sacred ruins of Delos, then on to the volcanic caldera of Santorini.
Athens layers five millennia of history into one walkable city — from ancient temples to vibrant neighborhoods still alive with the scent of olive wood smoke.
From the Acropolis ridge, the modern city spreads in every direction below — a grey-green patchwork of apartment blocks, neoclassical facades, and church domes. The Parthenon's honey-coloured columns catch the afternoon light while below, the streets of Plaka hum with the sound of serving spoons on clay dishes and the low murmur of Greek conversation.
Athens has been continuously inhabited for over three millennia, and the ancient sites are woven into the city rather than cordoned off as museum pieces. Walking through the Ancient Agora, you pass the weathered stones where Socrates once debated with young men who would later become his accusers. Fig trees shade the temple of Hephaestus, remarkably intact above the Stoa of Attalos. On Areopagus Hill, you stand where the Aeropagus Council met and where the Apostle Paul addressed the Athenians.
Monastiraki Square fills each evening with visitors and locals crowding the taverna tables spilling onto the flagstones. To the east, Syntagma Square marks the city's centre, watched over by the parliament building where the evzones — the ceremonial guards in their pleated skirts and pompom-topped boots — maintain their slow, precise march at the Tomb of the Unknown Soldier. The changing ceremony on Sundays draws a crowd.
At dawn, the city has a different texture. The smell of roasting coffee drifts from kafeneia that have been serving the same recipe for generations. Cat's eyes track you from doorways. By nine, the archaeology museums are opening their cool marble halls.
The Glypton Hill path leads to an open-air theatre carved from rock, still used for summer performances. From Lycabettus Hill, the whole city lies visible — the Saronic Gulf glinting to the south, the mountains of Parnitha and Penteli rising behind. The walk down through the pine-scented slopes brings you back to the city in its evening rhythm, when the neighbourhood ouzeri are filling with regulars and the first lights are coming on over the Acropolis.
Eight days island-hopping through the Cyclades — Athens, Syros, Mykonos and the sacred ruins of Delos, then on to the volcanic caldera of Santorini.
Our groups are capped at eight travellers, which is about a third of what the industry calls a small group. Eight people share one vehicle, one table at dinner and one guide's attention, and the day can change on the road without anybody being left behind. If you are looking for a coach, a fixed script and a microphone, this is not that.
Most days involve real walking, often on ground that was laid two thousand years before walking shoes: marble worn smooth, cobbles, uneven steps and long site paths with little shade. Bring shoes you can spend a morning in.
Some days move between regions and are largely a drive, with stops along the way. Summers are hot — well over 35°C inland — and winters are colder than most people expect, so layers, a hat and sunscreen earn their place in the bag whatever the month.
How demanding a particular trip is, is written on the trip itself: the physical rating in the header, and the day-by-day itinerary above.
Trip prices are per person, sharing a twin room. Each traveller picks their own room while booking, so a party can mix the three:
Solo travellers are welcome on every departure, and most of our groups have one or two aboard.
The hotels named in an itinerary are a guideline rather than a guarantee. Where one is full, or has dropped below the standard we booked it for, we substitute a property of a similar standard in the same area — we would rather change the hotel than the trip.
Check-in is usually mid-afternoon. If you arrive early we will ask for the room, but no hotel can promise one before its own check-in time; luggage can normally be left at reception in the meantime. If you want the room from the night before, ask us and we will add the extra night to your booking.
Entry requirements depend on your nationality and change without much notice, so the only reliable source is the official one: the government of the country you are travelling to, and your own foreign ministry's travel advice. Check both before you book a flight.
Many countries ask for a passport valid for at least six months beyond your travel dates, and for blank pages. It is worth looking at yours now rather than at the airport.
We ask every traveller to carry travel insurance covering medical treatment and repatriation, and we would strongly encourage cover for cancellation and for your luggage as well.
Once a departure is on the calendar it runs. We do not cancel a trip for want of a minimum number of bookings, so a booked date is one you can plan flights and leave around.
What can move is the shape of a day. Museums and archaeological sites change their hours, roads close, weather turns, a local holiday lands in the middle of the week. Where that happens your guide reorders the day, or swaps a stop for one of the same weight, and tells you why. Changes to a booked itinerary are covered by our Booking Terms & Conditions.