Anek ferry from Heraklion to Santorini........
 

and Blue star ferry from Santorini to Rhodes

For beginning of May, how soon do I need to get tix? Is there advantage in buying early online? Can I wait till I get to Chania? Will have my laptop with me, should I go through an agent?
I read the ferry departs early. I am thinking I can drive there with a rental car the day before, do some sightseeing on the way and spend the night either somewhere close to the ferry terminal or.....? What would you recommend for sight- seeing and spend the night? What car company allow drop off at a different location?
I think I read I should buy all the insurance policies that comes with car rental in Greece. My credit card comes with some of that stuff but I guess I should buy the whole package anyway, is that the case?

http://www.gtp.gr

So far I'm only finding the SeaJets Superjet for early May, nothing from Anek. You can wait until you're there to buy your tickets, the ferries wont' be full in early May. Just find a ticket agent in Chania, prices are fixed and they don't change during the year. You can drive a rental car or take a bus to Heraklion. Ask at your hotel for car rental agency recommendations. There are hotels near the port. Visit the archaeological museum if it's open and go to the Palace of Knossos just out of town. There's a bus to Knossos so you won't need a car. Definitely take out all the insurance coverage you can get locally. Be sure to go to your local AAA office to pick up an International Driving Permit, no test or membership required, for $15. Bring 2 passport photos with you so you don't have to pay the photo fee.

Wait until you are in Greece to buy the ferry tickets directly from an agent. There is no advantage to buying online except during high season and around Greek holidays.

You do realise the Anek ferry runs only twice per week, currently on Wednesdays and Fridays? Also, I would wait until Blue Star releases its May timetables to insure there is a ferry between Santorini and Rhodes. I have no reason to believe there won't be, but currently its only stop in the Cyclades is at Syros. Probably when summer timetables are released it will resume stopping at Santorini three times per week.

Incidentally, the same Anek ferry that runs from Heraklion to Santorini also goes from Santorini to Rhodes on the outbound leg of its journey — five stops in-between, though, so a longish trip. :-)

Thanks brother and Heimdall.
The ferry is an issue because am prone to motion sickness. I don't like enclosed space, as long as I have fresh air I should be fine. Do only Anek and Blue star have open space? When do their schedule for May come out?
I like art and history but love nature more. I want to see beautiful scenery in Crete. Where would you recommend? Plan to base in Chania but nothing is booked yet. Driving is OK. We are flexible.

The only ferries that don't have open decks are fast ferries (highspeeds, flying cats, and hydrofoils). There are dozens of companies operating conventional ferries with open decks. Greek ferries sail between the mainland and islands on defined routes. The problem here is that Crete, Santorini, and Rhodes are on three different main ferries routes, and cross-route connections are limited.

The Anek ferry (Prevelis) is a year-round route, stopping at many different ports in the Cyclades, Crete, and Dodacanese on two day round trips. Blue Star has a route from Piraeus to Kos and Rhodes, stopping at Syros in the Cyclades en route. For the last several summers it has stopped at Santorini on alternate days, but there is no way to be sure it will be stopping there in early May until timetables are released.

With a little patience and flexibility you should be able to work a route that avoids enclosed ferries. The Anek ferry stops at Santorini first, then goes on to Crete and Rhodes. On its return to Piraeus it reverses those stops, Heraklion first, then Santorini. You could, therefore, start your trip at Santorini, taking Prevelis to Heraklion. After spending time on Crete pick up the same ferry to Rhodes on one of its subsequent trips the following week.

Another possibility would be Santorini to Heraklion on Prevelis, and Heraklion to Rhodes by the Olympic Air Dash 8 flight.
:-)

Interesting...I tried a dummy booking on http://www.bluestarferries.com/site/...?sel=812&loc=2 for Syros to Rhodes and it is already showing sailings on Blue Star 2 in May and June 2012. When I tried doing the same for Santorini to Rhodes it came back with: "There is no sailing on this Day and/or this Route". It may be that a Santorini-Rhodes timetable will be added later in the spring, though. ((?))