Unless you plan to fly you don't have enough time to see 4-5 islands. You can get from Mykonos-Santorini-Crete easily enough by express catamaran, but Rhodes is a 13 hour ferry trip from Crete, assuming you can make the connection work.

I suggest you start by flying to Crete, to Chania, then make your way to Heraklion for the fast ferry to Santorini, and ending up on Mykonos. From there you can either fly back to Athens or take the fast ferry to Rafina and a bus back into Athens. Rafina and the airport are about the same time difference outside of central Athens.

Here are the links to the ferry websites as well as to Aegean Airlines, they're much more reliable than Olympic these days as well as less expensive.

www.gtp.gr

http://www.greekislands.gr/hfd/

http://www.bluestarferries.com/ENGLISH/defaultmain.htm

http://www.aegean-air.gr/aegeanen/home/

The most beautiful village on Santorini is Oia and May is the perfect month for a visit, warm and not too crowded.

Here's a list of hotels on Santorini separated by village and quality:

http://www.santorinihotels.com/hotels.php

If you want something really special, check out the Aspaki Suites at

www.artmaisons.gr

These are self-catering facilities with daily maid service, so beautifully decorated and with the perfect caldera view.

Hello. You will find fodor's people very willing to share info and experiences. But first please do a search, this question gets asked every week. Then you can ask more specific questions and people will be eager to help.

Thanks brotherleelove for the wealth of information you provided. Is there any way of seeing Hydra? Also, do you have any suggestions for any other beautiful hotels on the other islands? I remember travelling there years ago and thought it was a special island? Thanks, madvee

Thanks brotherleelove for the wealth of information you provided. Is there any way of seeing Hydra? Also, do you have any suggestions for any other beautiful hotels on the other islands? Thanks, madvee

I've heard Hydra is lovely, and no cars are allowed which makes it extra special. But never having been there I can't make any first-hand recommendations. I do know, however, that it's fairly close to Athens by ferry, only 1.5 hours by hydrofoil.

By the way, the express boat route from Crete to Mykonos also would allow you to stop at Ios, Naxos and Paros on the way to Mykonos, so you do have some other options.

Please note that those ferry websites I gave you are not going to give you current information for next May, you won't get that until late April or so. Also, the schedules can change without notice. The best and most reliable information will be found on each separate island a day before departure to your next destination. The good thing about May is that waiting until the last minute poses no problem as far as space available is concerned.

I must say that you have given me such excellent help. Can you recommend other hotels on the various islands which are centrally located and have good views? Thanks

The temperatures may be a little cool in May. My daughter and I were in Mykonos and Paros and the water was ice cold in May.

Paros is close to both Mykonos and Santorini, has some lovely beach areas, and the port town of Paroikia is interesting and offers much to see and do. Sorry, no hotel recommendations, but here's a link to a friend's website with inexpensive private apartments for rent:

http://parosparadise.com/

May is an excellent time to visit Greece, and it is possible to swim if you don't mind it a bit chilly. Certainly by the end of May (when I usually visit) the water is bearable.

For reasons stated above, recommend you eliminate Rhodes from your itinerary and stick with the Cyclades and Crete. Spend enough time in Mykonos to visit the island of Delos, and then move on. You could stop in Naxos or Paros on your way to Santorini.

Save Athens for the end of your trip. If you haven't had enough of the islands by then, Hydra is an easy day trip from Athens (Pireaus).

Thanks again for all your wonderful suggestions. If I eliminate Rhodes, what island/islands would you add the extra 3 days?
Also, I will be arriving in Athens at around 10 in the morning and want to know if it is advisable to stay there for the day, or head on to Mykonos leaving Athens entirely for the last part of my trip? Thanks

Naxos and Paros are both on the ferry route between Mykonos and Santorini, and either would be a good choice.

If you choose Paros, plan to spend one day on nearby Antiparos, a 30 min ferry ride from the main port of Paroikia, where you can see the cave and walk to the beaches. Paros itself has some interesting villages, a little flavor of island life away from the tourist areas.

Naxos, like Paros, is a fairly large island, with much to see away from the beaches.

Recommend you visit www.islandstrolling.com for some great photos and information about the islands. This is a private website run by a Norwegian who has been visiting Greece for many years. Some of the pages even have Greek music to get you in the mood.

It is always best to leave a couple of days for Athens at the end of your trip just in case weather or strikes stop the ferries running.

Whether you spend a day in Athens or go straight on to Mykonos is personal choice. You may be tired from your flight and want a day to recover. On the other hand, there are afternoon ferries to Mykonos departing each day from both Rafina and Pireaus. You can find a room with one of the many hotel owners waiting at the docks in Mykonos. You even get a free ride to the hotel (so you won't get poached by one of their competitors).

When you arrive at Athens Airport, get a copy of the Herald Tribune, which has an insert called Kathimerini, that shows all the day's ferry sailings from Rafina and Pireaus.

Hi madvee,
I think that it will be better to leave Athens for the end of your trip. You can do shopping there too...

I'm not sure where you're flying in from, but you could be really jet lagged the first day or two. My husband and I flew to Athens from Philly and he needed a full day to recover. We spent 3 days in Athens and then took a ferry to Spetses, 2 days, ferry back to Pireaus, then flew from Athens to Santorini for 4 days, one more day in Athens adn then an early morning flight home.

I would recommend the longest time on Santorini - beautiful! We stayed at the Oia Mare and would 100% recommend it. If I could do it again I'd cut out Spetses entirely and take the entire time on Santorini.

Hi Madvee: I'm so jealous you get to go to beautiful Greece! I, too, had an 18-day trip this summer. I took a cruise that stopped on exactly those islands you mentioned (plus Turkey). Except for Hydra, which we went to separately. The cruise was not for me, but perhaps you would be better suited for it. I felt rushed and the accommodations were uncomfortable. We chose our cabin poorly and perhaps should have opted for a longer cruise.

But, you might check into it:
http://www.travel-guide-greece.com/Cruise-greece/greek-islands-mediterranean/golden-adventure.asp

I believe it was Golden Star Cruises.

If I could do it all over again, I would have gone to Santorini or Mykonos and stayed for a few days.

Also, I must say that Hydra was the absolute highlight of my trip. So quiet, peaceful, beautiful. We stayed at the Hotel Angelica and would highly recommend it. Just be aware that there is no sandy beach in Hydra - there is a rocky beach a short boat ride away. But it's really a peaceful place to explore.

Somehow I just can't see the point of taking a cruise in the Greek islands when ferries run like buses. The middle of May is the perfect time to travel there independently - hop on a ferry, stay on an island as long as you like, then move on. There is a surplus of accommodation that time of year, so reservations aren't even necessary.

I realize this sort of travel doesn't appeal to everyone, but if you have a sense of adventure you will enjoy it.

I would like to thank everyone for their responses. I still have not firmed up my plans. I would like to get deluxe accomodations in Santorini with caldera views. Any recommendations would be welcome. Has anyone stayed at the Porto Fira Suites there? If so, what is it like? Also, I need hotel recommendations for Chania. Has anyone stayed at the Porto Veneziano there? What did you think of it? How is the Mykonian Ambassador Thalasso Spa in Mykonos? Has anyone stayed at the Rhodos Park suites in Rhodes? Thanks, madvee

Can't help you with Fira, but in Oia you have your choice of several luxury hotels: Esperas, Katikies, Perivolas, Oia Mare, The Residence, La Perla, Fanari, Canaves. If you prefer self-catering, check out the luxury Aspaki Suites.

Thanks brotherleelove, but would Oia be as much fun as Fira for a 19yr. old?

Probably not if "nightlife" is a preference. Oia doesn't have any discos or any singles scene to speak of. At night the restaurants and a couple of quiet bars are the only options.

Thanks Brotherleelove. How far is Fira from Oia? Which do you think is a better place to stay, Porta Fira or Katoikes in Oia?. By the way, I took your advice and I am not going to Rhodes, but I am still going to 4 places, Athens for 3 days, Mykonos for 4 days, Santorini for 5 days, and Crete for 5 days. Do you think it is still too many islands and what do you think about the time I have alotted for each?

I've never seen the Porto Fira so I don't have anything to compare it to.

The Katikies properties (one now renamed Kirini) are all quite lovely. The excellent service and amenities there are well-documented. Katikies has the added bonus of being in Oia, which for me is much more desirable than Fira. Be aware that Katikies and Kirini are more expensive than Porto Fira.

I did have a look at the Porto Fira website, and it appears that this hotel is not actually right in Fira, but a short distance away. If you want to stay there I recommend you ask how far a walk it is to the bus square in Fira. This will give you an idea of your location and the time you might spend getting to and from the shopping and restaurants. It might require a taxi each time you do.

I don't think 3 islands is too many. As long as you can make your connections between them on the days you choose to travel, and as long as you plan to fly back to Athens from Crete you should be fine. Keep in mind that the highspeed ferry that connects Mykonos to Santorini and Crete will probably not be making a daily run in mid-May, if last year's timetable is any indication.

You say that Oia better like better than Fira, but how long does it take to get between the two? Thanks once again for all your help.