Two Weeks in the Greek Islands: Three Routes

Two weeks in the Greek islands is the first length that gives you a real choice. Ten days forces the standard Cycladic run; see the 10-day itinerary for that. Fourteen nights buys four Cycladic islands at a civilized pace, or one big island done properly, or a Cyclades week and a jump to the Dodecanese. Here are all three, and which is yours.

What two weeks does not buy is seven islands. The arithmetic has not changed: every island change costs roughly half a day once you pack, wait, sail and find your room, and three nights per island is the sensible floor.

The three routes at a glance

Route	Shape	Best for
1. The Cyclades Four	Mykonos or Paros, Paros, Naxos, Santorini, Athens	First-timers who want the postcard Greece and do not mind crowds
2. Crete Properly	Chania, Rethymno, Agios Nikolaos, Heraklion	Drivers, walkers, eaters, anyone tired of packing
3. Cyclades and Dodecanese	Naxos, Santorini, Kos, Rhodes	Repeat visitors who want two different Greeces in one trip

Why the shapes differ

Route 1 works because everything on it sits on the main corridor out of Piraeus, which in summer carries up to eight to ten sailings a day down to Santorini. Fallbacks everywhere. Route 2 removes ferries from the equation almost entirely: one crossing in, one flight out, and a car for the rest. Route 3 is the only one that crosses between island clusters, which is the classic island-hopping trap and needs a whole day budgeted for it.

All three end where your flight home is. Route 1 returns to Athens for a buffer night, because Athens has the flight volume and the airport hotels Santorini does not. Routes 2 and 3 end on islands with direct European summer flights — Heraklion and Rhodes — which is what lets them skip the return leg. Read the ferry guide before committing to any of them.

Route 1: The Cyclades Four

Nights	Where	Why
3	Mykonos, or Paros again	Delos, the Chora, the nightlife. Expensive and windy. Paros is the cheaper substitute.
3	Paros	Naoussa, Lefkes, beaches on every coast, buses that work.
4	Naxos	The one to give an extra night: mountain villages, kouroi, the longest sand beaches in the Cyclades.
3	Santorini	Caldera walk, Akrotiri, and then leave before the prices wear you down.
1	Athens	The buffer night before your flight.

Sail from Rafina if you start on Mykonos — 30 to 40 minutes from the airport by bus for €3 to €4, fastest crossing 1h50 — but Rafina is more exposed to the meltemi and has fewer fallback sailings than Piraeus. Mykonos is the island the wind hits hardest and the most expensive after Santorini. If neither Delos nor the nightlife is the draw, skip it: start on Paros from Piraeus and give the spare nights to Naxos.

The moves are all short: Mykonos to Paros and Paros to Naxos are about an hour each, Naxos to Santorini around two on a fast boat. Coming back, a conventional ferry from Santorini to Piraeus costs from about €50 and takes five and a half to seven and a half hours — only an hour slower than the quickest catamaran, and far more likely to sail in wind.

Route 2: Crete Properly

Nights	Where	Why
5	Chania	Venetian harbor, the west: Elafonissi, Balos, Falasarna, and the Samaria Gorge as a full day out.
3	Rethymno	Old town, Preveli, the road up into the Amari valley.
3	Agios Nikolaos	The east: Spinalonga, the Lasithi plateau, Vai, quieter beaches.
3	Heraklion	Knossos, the archaeological museum, and an airport to fly home from.

Crete is the argument against island hopping. Moving between bases feels like a road trip rather than a ferry day, and both airports, Heraklion and Chania, take direct European summer flights. Fly into Chania, drive east, fly out of Heraklion. No Athens buffer night is needed, because your last night is already at the airport you leave from. By sea, Piraeus to Heraklion starts around €33 and takes six to fourteen hours, mostly overnight.

You need a car. There is no version of Crete that works well on buses, and the best parts — the gorges, the south coast, the mountain villages — are exactly what buses do not reach. Four bases in fourteen nights means one move every three to five days, the calmest itinerary on this page.

Route 3: Cyclades and Dodecanese

Nights	Where	Why
4	Naxos	The best all-round Cycladic island, and a hub with frequent boats.
3	Santorini	The caldera, before you leave the Cyclades entirely.
1	In transit	The cluster crossing. Budget the whole day and do not plan anything else.
3	Kos	Flat, green, easy cycling, Roman ruins in the middle of town.
3	Rhodes	The walled medieval city, Lindos, and a direct flight home.

This is the ambitious one, and the only route here that breaks our own rule about crossing clusters. Cyclades to Dodecanese sailings exist but run a handful of days a week rather than daily, often overnight and often via Astypalaia or Kalymnos. Check the timetable for your dates before booking anything else: if the day does not line up, the honest fix is to fly. Athens to Rhodes and Athens to Kos are short domestic hops, and reversing the route — Dodecanese first, home from Athens — is often easier to schedule.

The reward is that the Dodecanese feel like a different country: Ottoman and Italian layers on top of the Greek, greener islands, a Crusader castle in the middle of Rhodes town. Both Kos and Rhodes have direct European flights, so you finish without doubling back.

Which one is yours

• First trip to Greece, want the images you have already seen, traveling in June or September: Route 1.
• You drive, you walk, you would rather unpack once and eat well: Route 2, also the best of the three for families.
• You have done the Cyclades, you like logistics, and a lost day in transit does not ruin your holiday: Route 3.
• You want quiet above all: none of these. Take the western line instead — the quiet Cyclades itinerary.

What these itineraries are not

None of them is off the beaten track. Routes 1 and 3 both include Santorini in high summer, the busiest place in the country. If crowds are what you are avoiding, go in October — see the best Greek island in October — or switch to Sifnos, Folegandros and Milos on the western line, a different set of boats out of Piraeus.

Route 3 is not for a first visit. If these are your only two weeks in Greece for the foreseeable future, spend them on Route 1 or 2 and come back for the Dodecanese. And with ten days rather than fourteen, do not compress any of these — use the 10-day itinerary instead.

What it costs

Indicative, per person, for fourteen nights, excluding flights to Greece.

Route	Transport within Greece	Rooms and food, shoulder	Rooms and food, July–August
1. Cyclades Four	€160–230 in ferries	€1,500–2,200	€2,400–3,600
2. Crete	€45–90 ferry or a domestic flight, plus €350–600 for a car	€1,300–1,800	€1,900–2,700
3. Cyclades and Dodecanese	€180–280 in ferries, more if you fly a leg	€1,400–2,000	€2,100–3,100

Crete is the cheapest per night and the only one where the car is a required cost rather than a convenience. Santorini is the biggest variable on Routes 1 and 3: caldera-view rooms can double the accommodation line for those nights. See also the cheapest Greek islands.

Booking this trip

Still deciding? Take the island quiz, then read the ferry guide, because on all three routes the boats decide the itinerary and not the other way round. The shorter versions are on the island-hopping hub.

Frequently asked questions

How many islands can you visit in two weeks in Greece?

Four, comfortably, if they sit on the same ferry line. Five is possible and usually regretted. One large island such as Crete for the whole fortnight is a legitimate answer rather than a consolation prize.

Is two weeks in the Greek islands too long?

No, but two weeks of packing every third morning is. The complaint after a long island-hopping trip is travel fatigue, not boredom, which is why every route here slows down rather than adding stops.

Can you ferry from the Cyclades to the Dodecanese?

Yes, but not daily. The links run a few days a week in summer, often overnight and often calling at Astypalaia or Kalymnos, and a Mykonos to Folegandros style hop between clusters can take over five hours with long waits. Budget a whole day, check your dates first, and treat a domestic flight via Athens as the fallback rather than a failure.

Last updated 2026-09.