The ferry dock area in Santorini was very crowded when the ferry arrived, chaotic. We had the hotel pre-arrange a taxi for us and I was so glad that we did that.
Why don't you stay near the ferry in Heraklion the night before?

If you have a choice go with the Hellenic Seaways FlyingCat4. The SeaJets Superjet isn't as reliable. It has a history of breakdowns.

As far as comfort and amenities they're about the same. If the seas are rough it won't be very comfortable.

In May you can buy your ferry tickets in Chania a day or two in advance at a reliable travel agency your hotel will recommend. Do this and save yourselves the stress of having to buy them at the last minute the morning of your departure for Santorini. Seats are assigned at the time of purchase. Try to get seats along the centerline of the ferry so the side-to-side rocking motion will be kept to a minimum.

Santorini's port won't be crazy-busy in May. You will have the option of taking a taxi to your hotel or you can take the port bus into Fira and make your way to your hotel from there. You can also rent a car at the port if you want one. Your hotel may also offer a transfer service which can simplify things.

Considering it takes 2-2.5 hours to make the trip, there is nothing else available in the early morning from Chania to Heraklion besides the bus unless you want to rent a one-way car.

I agree that FlyingCat 4 is preferable to Superjet. Sea Jets Consortium also operates a much larger catamaran, Megajet, on the Heraklion - Santorini route. Magajet is a car-carrying catamaran, and would be more stable in rough seas than FlyingCat 4. Last year Megajet began its season on May 27th, so might or might not be running on that day in 2013. No need to rush into making a booking — wait until all the ferry timetables are out and then decide. I always buy my ferry tickets after arrival in Greece.

Unfortunately there are no later options for ferries from Crete to Santorini. The catamarans doing that run are all based in Heraklion, making round trips from there, leaving Heraklion in the morning and returning in the evening.

If you were willing to leave a day earlier, Prevelis, a conventional ferry, departs Heraklion on Sundays at 4 pm and arrives on Santorini at 9:40 pm. You will have to wait until next spring to confirm, but this is a year-round route and changes little from month to month.

Outstanding. And greatly appreciated.

bdj

When Lee states to book the ferry in Chania at a "reliable" travel agency - how does one make the distinction? We are staying in an apartment and will not have the luxury of staff assistance.

If unable to purchase advance tickets for the ferry in Chania, just how stressful is the process of deboarding, finding the proper ticket office, purchasing the precise tickets and catching the ferry?

Given the KTEL bus leaves at 5:30am, are tickets for that purchased in advance as well? If not, what time should one arrive at the station to secure tickets, luggage and a seat?

Finally, is there ANY chance that both the bus and ferry tickets can be purchased at the same venue in advance? Can one get a ferry ticket at the bus station?

Much obliged...bdj

Maria Mylonaki at Diktynna Travel in Chania is an excellent incoming tourist agency specializing in Crete; agents worldwide book their Crete portions through her. She arranged out trip there for us. She may not deal with something as small as bus or ferry tickets but if not, at least she can lead you to a good agency in Chania to help you.
sales@diktynna-travel.gr
www.diktynna-travel.gr

The busses to Heraklion, leave from a very very central square of Chania. You can buy bus tickets a couple of days in advance if you want.

There are many travel agencies in Chania, so finding one to buy the tickets should be easy.
All travel agencies are reliable in the city of Chania, i wouldn't worry about that. It also makes no sense to compare prices, as the tickets have one price, regardless of where you buy them.

You can't buy KTEL tickets anywhere else than at the KTEL office, that is near 1866 Square.

Diktynna is a good incoming ( and not only) agency, but as i said all travel agencies in the city of Chania are reliable, buying them in the old town would be the easiest option.

I remember seeing a travel agency as you walk down the main street to the old town ( Chalidon Street)

Just look for the Hellenic Seaways logo sticker in the window of the travel offices. That's where you'd want to buy your tickets.