Athens to Santorini: Greek Island Hopping
- # History & Archaeology
- # Coast & Islands
- # Photography
- # Summer Vacation
About this trip
Eight days island-hopping through the Cyclades — Athens, Syros, Mykonos and the sacred ruins of Delos, then on to the volcanic caldera of Santorini.
Itinerary
Day 1 Athens
Kalimera — welcome to Greece. There is little time to explore Athens before the ferry leaves for the islands, so arriving a day or two early is worthwhile if your schedule allows. The changing of the guard at Syntagma Square, the National Gardens, the Temple of Olympian Zeus, the original Olympic Stadium and the Acropolis are all within walking distance of the old town.
After this evening's welcome meeting, step out for gyros and a glass of ouzo with your travel companions.
Day 2 Syros
This morning you take the metro down to the port of Piraeus and board the ferry south into the Cyclades. The crossing to Syros takes about four hours; the Aegean runs from pale aquamarine to deep blue as the islands come into view.
In the heart of the archipelago, Syros is one of the Aegean's most underrated islands — whitewashed houses, terraced fields, sandy coves and the elegant port of Ermoupolis with its neoclassical mansions and 19th-century tenement blocks. Your leader takes you for an included lunch at a traditional taverna before a walk through town. Stop at a family-run loukoumi workshop to see how Greek Delight and chalvadopita are made, then settle at a waterfront cafe as the setting sun turns the housefronts pink.
Day 3 Syros
Morning walk through the fortress-like hill town of Ano Syros, narrow alleyways stacked above the harbour, handmade-souvenir shops and traditional Rembetiko music drifting from family-run tavernas. The rest of the day is free — abandoned windmills on stone-paved tracks, the small archaeological sites around the island, the quieter coves outside Ermoupolis, or simply a beach afternoon on the southern side.
In the evening, taxis take the group to a remote village in the rugged north of the island for an included dinner — local specialities and the sun going down over the Aegean.
Day 4 Mykonos
A two-hour ferry delivers you to Mykonos, the chic Cycladic island named after Apollo's grandson. Your leader walks you through the maze-like old town — squat white houses set against the cerulean sea, chic galleries, flower-lined paths past age-old churches and tiny restaurants tucked down to sandy coves.
After checking into the hotel, the afternoon is yours: swim, snooze on the beach, or walk out along the water to the row of stone windmills above the harbour. Sunset brings Europe's party crowd out; a backstreet taverna keeps things simpler.
Day 5 Delos
This morning a half-day boat trip takes you out to the nearby island of Delos — once the political and religious centre of the Aegean, sacred as the mythological birthplace of Apollo and Artemis. The Terrace of the Lions, the Sacred Precinct, the mansions decorated with frescoes and mosaics: the island is essentially one open-air museum, with more still being uncovered.
Back on Mykonos in the afternoon, a beach, the 19th-century House of Lena, the Aegean Maritime Museum or a taverna in the village of Ano Mera are all options. Sunset is best watched from Little Venice, where colourful balconies hang over the sea.
Day 6 Santorini
A ferry ride of about two and a half hours brings you to Santorini — the iconic image of the Greek islands, whitewashed, blue-domed buildings clinging to the cliff face with the sparkling Aegean below. On the way in, the ferry passes between the two halves of the submerged caldera.
From your base in the village of Karterados, walk into the island's capital Thira (also called Fira) for restaurants and shops, or explore the hilltop ruins of Ancient Thira and the Minoan Bronze Age site of Akrotiri. The island's volcanic beaches — Red Beach, Perissa, Perivolos, Agios Georgios — are an easy bus ride away. The local food is unusually good: Santorini's vines grow in basket shapes low against the volcanic soil, and the cherry tomatoes, fava and white eggplant that grow the same way are the basis of the cuisine.
Day 7 Santorini
About 3,500 years ago the centre of Santorini sank in a volcanic eruption, forming one of the most significant geological formations on the planet — the awe-inspiring caldera. Today you walk along the crater rim from Thira town to Oia, passing little white villages, steep cliff faces and endlessly blue water below.
If the full hike is not for you, the bus runs the same route and you can meet the rest of the group in Oia. A half-day boat trip to the volcano and hot springs in the centre of the lagoon, or a tasting at one of the island's wineries, are alternatives. End the day among locals at a cafe on the cliff as the sun drops into the sea.
Day 8 Santorini
Your Greek Islands adventure ends this morning in Santorini. There are no activities planned and you are able to leave the accommodation at any time. If you would like to extend your stay, we are happy to book additional accommodation, subject to availability.
Before you book you should know
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Is this trip right for you?
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.
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Rooms, and travelling on your own
Trip prices are per person, sharing a twin room. Each traveller picks their own room while booking, so a party can mix the three:
- Twin share — two single beds, shared with someone you are travelling with or with a traveller of the same gender.
- Travelling as a couple — one double room.
- Individual room — a room of your own, for a single supplement on top of the trip price. Availability is limited, and the supplement for a given date is shown next to the option when you book.
Solo travellers are welcome on every departure, and most of our groups have one or two aboard.
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Accommodation
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.
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Passports, visas and insurance
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.
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Your departure is guaranteed — the day can change
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.
Choose a departure date
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Nov. 15, 2026 8 spots left