Best transportation for Greek Island Hopping

That's an awful lot of places for two weeks. Crete is a really large island--not the sort of place that would be recommended for only 3 nights, and you have barely more than an average of two nights per stop. I would definitely shelve Crete for next year. You'll need a second trip to Greece. (That's good news.)

Exactly how many nights will you have in Greece (not counting the overnight flight)?

Mykonos and Milos seem to have flights only to and from Athens, not to other islands. Santorini has service on Ellinair (never heard of it) to Heraklion, Crete, as well as Athens.

Between the islands, most travelers take ferries. Several companies provide ferry service.
Olympia is wonderful but you plan to travel far to the Western side of the Peloponnesean Peninsula without seeing any other places in that area, or in the eastern areas, Mycenae, Napflion?

Ferries are definitely part of a Greek experience. Some are fast and some are slow. You pay more for the faster ones. There are also different classes with different experiences. Some of the really nice ones have reserved seating like airplanes.

Hydrofoils are the fastest but also the most likely to cancel due to high waves.

I’d suggest taking a flight to one island and taking ferries to other islands nearby.

If you have a long ferry ride and you're expecting to be tired (or jet-lagged), I highly recommend spending a small amount more to book a cabin. We thought it was a great bargain after comparing our comfort (four bunks for the four of us and a good shower!) to what people were putting up with elsewhere on the boat. Most were fine, to be fair, but some were trying to snooze in extremely awkward spots.

Also, having traveled in Greece twice I'm no expert like some here, but I strongly endorse their advice to cut your list of destinations. Crete could fill up your whole time. Also, if you're not going to famous places because they're famous, consider omitting over-touristed Santorini and Mykonos, to spend more time on the rest of your destinations.

Also, having traveled in Greece twice I'm no expert like some here, but I strongly endorse their advice to cut your list of destinations. Crete could fill up your whole time. Also, if you're not going to famous places because they're famous, consider omitting over-touristed Santorini and Mykonos, to spend more time on the rest of your destinations.

hi er -- When you want useful advice, best to share more facts. "Next summer" covers up to 5 months, and July-Aug is Waay different from June or September... hotter, vastly more crowds, costlier.

Agree with previous posters: too man destinations. Did you look at a map?. To even spend a couple of days in each, you'd need to have the Star-trek teleporting device ("beam me up Scotty") to instantly get from one place to another.... in fact it takes at least 1/2 day, sometimes a day. Crete isn't an "island" like others, it's more like a country -- think Californa, but with no trains, no planes. Crete has only one big road along the north edge, small roads curving around mountains to reach south, NO road along south coast. Hmmm.

Clicking your name, I see you've been to France, Italy Switzerland, and you can cover a lot of ground on their excellent train systems. Greece right now, has virtually NO trains. Intercity busses are modern & used by all classes of society, but don't go everywhere.

If you want Crete, a realistic list, and do-able sequence might be something like this:
ARRIVE in A.m. - day 1 -- fly to Westernmost town of CRETE (CHANIA) 2 days, rent car, drive S then No to HERAKLION area
FERRY am DAY 6 - Santorini (2 days) FErry to MILOS 3 days)
Fly on day 11-12 to ATH (3 days)

I will be a bit contrary about Crete, yes, it is large, yes, you could spend weeks, but you could just hit Heraklion if that is what interests you, or just Chania, just like any other island or country, they won't revoke your travel card.

My concern with your itinerary is flow. Athens, Mykonos, Santorini, and a quick jaunt to Crete is not bad for two weeks, since that pretty much follows the ferry route, giving you 3 nights at each island and a good buffer in Athens on each end.

Olympia however is not a quick jaunt from Athens, figure 3 days and 2 nights minimum, maybe less with a bus tour or if you have a car. Your only option is really out of Athens and back into Athens, so if you miss a connection to mykonos on your travel day for example, it may mean another night in Athens.

Milos is another issue. It can be reached from Santorini, or Athens, but not easily from Mykonos or Crete, so you are probably looking at Santorini to Milos, then back to Santorini before heading to Crete, maybe having to do another night in Santorini, there may also be the issue that ferries are not running on the day you need it.

Basically, transport between islands, and even on the mainland, is not quick, figure for the transfers you are looking at a good chunk of the day, and often the best part of a day, will be travel. Second, transfers follow very specific routes. You cannot just pick two spots and go directly from one to the other, sometimes the island you can see on the horizon may mean going back to Athens, staying overnight, and then to that island, blowing two days and a night. Even flights (each of those islands have airports) mostly fly only from the island to Athens, or vice versa, not island to island. Lay out connections first, then figure at least two nights, probably three at any stop, then add up from there.