Greece · Itinerary · Updated September 2026
14 days in Greece: Athens and three Cyclades islands
Island-hopping is sold as freedom and is really a ferry timetable. Which islands you can string together depends almost entirely on which group they are in, so this route picks one group and stays in it. Fares and fees checked September 2026.
Length
14 days
Budget
€2,390 / $2,771
per person, mid-range
Best season
May–Jun, Sep–Oct
July and August are hot, full and double the price
Stops
5
4 bases, 3 ferries, one island group
The route
Three nights in Athens, then Naxos, Mykonos and Santorini, all Cyclades, all on the same ferry line.
Day by day
Days 1–3 · Athens
Three nights, and book the Acropolis before you fly
The Acropolis is €30 with **mandatory timed entry**. You choose a one-hour window when you buy, the site is capped at 20,000 visitors a day, and in June to August it sells out five to seven days ahead. Book it from home. Take the earliest slot: by eleven the rock is full and there is no shade on it. The Acropolis Museum is the other unmissable one, and the rest of Athens is free: Anafiotika, the Sunday flea market at Monastiraki, and the hill of Filopappou at sunset.
Sleep: Koukaki or Plaka for walking; Exarchia for cheaper and livelier.
Days 4–8 · Naxos
Five nights on the island that can hold them
Piraeus to Naxos is 3h15 on the fast ferry, from about €52. Naxos is the biggest Cyclade and the only one on this route with an interior: the mountain villages of Halki and Apiranthos, the marble quarries with their abandoned kouroi lying in the grass, Mount Zas if you want the walk, and a west coast of long sand beaches that never fill the way Mykonos does. Hire a car for two of the five days.
Sleep: Naxos Town for the harbour and the tavernas; Agios Prokopios for the beach.
Days 9–10 · Mykonos
Two nights, and Delos is why
Naxos to Mykonos is 35 minutes to an hour and a half, €30–58. Two nights is the right dose of Mykonos: one evening in the town, which is genuinely beautiful before the clubs open, and one full day for Delos. The boat goes from the old port and the island is an entire abandoned ancient city with nobody living on it. Mykonos is the most expensive bed in the Cyclades and the least interesting daytime.
Sleep: Mykonos Town or Ano Mera inland, which is a third of the price.
Days 11–13 · Santorini
Three nights, and stay on the wrong side
Mykonos to Santorini is from about €82.50, the priciest leg on the route. Stay in Oia or Imerovigli and you pay for a caldera view you will spend most of the day away from. Stay in Pyrgos or Megalochori inland and you pay half, eat better, and take the bus to the rim for sunset like everyone else. The caldera walk from Fira to Oia is three hours, best started at seven in the morning.
Sleep: Pyrgos or Megalochori inland. The view costs double and you sleep facing a wall anyway.
Day 14 · Santorini airport
Out from the island, not back through Athens
Santorini's airport flies internationally through the season and to Athens year-round. Ending here rather than ferrying back to Piraeus saves a full day, an eight-hour boat or a flight plus two transfers. Book open-jaw: into Athens, out of Santorini.
Sleep: Nowhere. This is the day you leave.
Best things to do on this route
If you cut the trip short, these are the ones to keep.
- 01
Delos, from Mykonos
An entire ancient city with no modern town on top of it and nobody living there. The best archaeological site in the islands and the reason Mykonos is on this route.
- 02
The Acropolis on the first slot of the day
€30 and timed. At eight it is cool and half empty; by eleven it is neither, and there is no shade anywhere on the rock.
- 03
The mountain villages of Naxos
Halki and Apiranthos, an hour inland by car. Marble streets, no cruise passengers, and the only interior of any island on this route.
- 04
The Fira to Oia caldera walk
Three hours along the crater rim. Start at seven, finish before the heat, and you will have most of it alone.
- 05
Filopappou hill at sunset
Free, ten minutes from Koukaki, and the view of the Acropolis that the Acropolis cannot give you.
Where to stay
Neighbourhoods rather than specific hotels. Prices move, areas don't.
Athens: Koukaki or Plaka
Koukaki is quieter, cheaper and five minutes from the Acropolis Museum. Plaka is prettier and priced for it.
Naxos: Town or Agios Prokopios
Naxos Town for tavernas and the ferry; Agios Prokopios for the beach and a ten-minute bus into town.
Mykonos: Ano Mera, not the town
Inland and a third of the price. The town is twenty minutes by bus and you will not want to be in it after midnight anyway.
Santorini: Pyrgos or Megalochori
Inland villages at half the caldera price, with better food and a bus to the rim. The view costs double and you sleep facing a wall.
What it cost
Per person, 14 days. International flights not included.
| Category | Cost |
|---|---|
| Accommodation: 13 nights | €1,105 / $1,281 |
| Food and drink | €700 / $811 |
| Ferries: three legs | €185 / $214 |
| Local transport and two days of car hire | €150 / $174 |
| Activities and entry fees | €120 / $139 |
| Climate resilience fee | €65 / $75 |
| SIM, laundry, everything else | €65 / $75 |
| Total | €2,390 / $2,771 |
Converted at €1 = $1.1593, checked 2 September 2026. About €171 a day, between the €120–160 usually quoted for island-hopping and the €150–250 for Greece generally. The gap is the ferries, which no mainland trip pays. The climate resilience fee is charged per room per night and is easy to forget: €5 at a three-star between April and October, €10 at a four-star, dropping to €1.50 and €3 from November.
Getting around
Stay inside one island group
This is the whole trick. Naxos, Mykonos and Santorini are Cyclades and sit on the same ferry lines, so the connections are frequent and direct. Adding Crete, Rhodes or Corfu means routing back through Piraeus or flying, and either way a day. The freedom people imagine belongs to whichever group they started in.
The three fares
Piraeus to Naxos from about €52, 3h15 on the fast ferry. Naxos to Mykonos €30–58, 35 minutes to an hour and a half. Mykonos to Santorini from about €82.50, the dearest leg. Book ahead in July and August, when boats sell out; outside that, a day or two is enough.
Book the Acropolis before you fly
€30, timed entry compulsory, 20,000 visitors a day, and it sells out five to seven days ahead in peak season. It is the one ticket on this itinerary that cannot be bought on arrival.
Fly out of Santorini
Ferrying back to Piraeus costs eight hours or a flight plus two transfers. Open-jaw into Athens and out of Santorini usually costs the same as a return and hands you a full day back.
Photos
Packing notes
The things that are annoying to find locally, or that people forget.
- Shoes with grip. Cycladic villages are marble and stone worn smooth, and Santorini's caldera path is loose scree in places.
- A hat and real sunscreen. There is no shade on the Acropolis, on Delos, or on the caldera walk.
- Seasickness tablets. The Aegean gets rough with the meltemi wind between July and September, and the fast ferries feel it most.
- Timed Acropolis tickets bought from home, before anything else on the trip.
- A light jacket for the evenings. The meltemi drops the temperature more than people expect.
- Cash for small tavernas and island buses, though cards work nearly everywhere now.
Why three islands and not six
Because each hop costs a morning. You check out, you get to the port, you wait, you sail, you find the new place, you buy food again. Two nights somewhere is one full day there and two half-days of logistics.
Six islands in fourteen days is six of those, which is most of a week spent moving between places you then see for a day each. Three islands means three ferries and a genuine sense of what each one is like, and Naxos, at five nights, is the only island on this route you could actually describe to someone afterwards.
The one rule that decides your route
Islands connect within their group, not between groups. The Cyclades (Naxos, Paros, Mykonos, Santorini, Milos, Ios) are a network with frequent direct boats. The Dodecanese (Rhodes, Kos, Symi) are a separate network. Crete, Corfu and the Ionian are separate again.
Every itinerary that mixes them spends days routing through Piraeus or flying domestically. If Rhodes is what you want, plan a Dodecanese trip; it is a better holiday than a Cyclades trip with Rhodes bolted on.
What is deliberately not here
Crete, which deserves two weeks on its own and cannot be a stop. Paros, which is genuinely lovely and is the fourth island most people add. It comes at the cost of two nights on Naxos, and Naxos is the better island. Ios and Paros as a chain, which turns this into the six-island trip above.