Christina--I think your friend is the guy who rented me my boat; he spoke with a kind of funny accent, I couldn't quite place it. But quasi-Greek sounds about right. From where in Quasi does he come?

well, if you only have 2 weeks, deifnitely do not try to do more than 3 islands. Santorini is a must. it is absolutly stunning. you can spend a week there easily. there are plenty of posh accomodations. Paros is nice too. beautiful beaches and there is this very nice restaurat right next to the sea. very very romantic!

Crete is a wonderful island, and big enough to have some high end accommodation, if not roads. You could fly there from Athens, i think, then boat to santorini.

Otherwise, i like the cruise idea as the best fit for your needs.

Good luck!

Ever tried doing some research for yourself first and then asking specific questions. When you say 'all these islands' do you mean the whole 2,000, you will be away for a long time won't you.

First, Thanks for all the replies, by saying "No backpackers" don't get me wrong, been there done that, just too old and crotchety, OK so Santorini seems like a must, also big marks for Mykonos (from some)and of course 2 days in athens is a must...So what kind of itenerary can people suggest from NA (Montreal) and again what are the popular ways to get from island to island...fly...boat etc...

oneillchris - why don't you rent a fully-staffed yacht? If we were a five-star family, that's what we'd do.

I am booked on a cruise to Greece in May. We are starting in Athens and ending in Istanbul including some of the islands. I have been to Santorini and can't wait to go back-it is so beautiful.

There are upscale ships that you will be very pleased with and all you need to do is choose excursions in advance if you like everything planned out and paid for, and you will be good to go.

I suggest the discreet 5* M/Y Ekali from Amphytrion.gr or M/Y Proton.

Sorry it´s amphitrion.gr

Well, chris, if you are so "five star" (meaning, I guess, that money is no object), go to any travel agency and get professional help, period. Rather than wasting the time of posters who are here to give free advice to people who actually enjoy travel.

Chris - I think what many people here are trying to say is that you sound like a real do*che bag. IBM and 5 star family. This sight is not for or about backpackers. It is for people who actually enjoy travelling and there is advice for all budgets from luxury to backpackers.

Geez, why is everyone being so nasty? Greece can be all things to all people. Just last summer, my husband and I thought it would be fun to do the overnight ferry from Santorini to Athens (ie. we did the backpacker thing). Well, at the end of the trip we just looked at each other and said 'never again'! Chris, there are many lovely places you can stay in Santorini - have a look at www.slh.com for some ideas on luxury. It is by no means exhaustive but gives you a good idea of what's out there. Here are some more sites which might help:

www.chicretreats.com
www.i-escape.com
www.mrandmrssmith.com

Happy to help you plan - I think you will find Greece surprisingly beautiful and unforgettable...

this looks like a lovely place to stay on Santorini...
http://perivolas.gr/
Being more of a 'backpacker' type, I tend to stay in the smaller, family run pensione's in the villages so I can get a feel of the local culture, get to know people who don't speak my language (while I am trying to speak theirs!), be able to walk into the village and sit by the harbor for a tsipouro and mezes... BUT, that said, I'd love a week at Perivolas!

Hi Dukey, sorry I didn't mean to sound condescending. I just wanted to give oneillchris a broader picture of travels in Greece. My husband's half Greek and his family still maintains a farm there. Quite honestly, after many trips to Greece, I have to say that my favorite moments were not sleeping in the same suite that Michael Eisner slept in the week before or hiring the same private boat that Angelina Jolie chartered a few weeks before. My best times have been in the little inns and tavernas that would be of no consequence to a "luxury" traveler. I can't back down on this one. Greece is different, in many respects, than most destinations.

I have to share a funny story...one of my husband's former clients was a wealthy Greek-American who was invited to go on a fully paid Greek Islands Cruise with one of his clients. He told us he that he and his wife finally couldn't take it anymore, packed their bags and jumped the boat in Mykonos. The captain of the cruise ship chased them down, trying to convince them to get back on the ship. Instead, they paid some guy on a motorcycle with a sidecar, to take them to the nearest hotel. That's Greece and the Greeks for you!

Oops, I don't want to offend anyone or start a battle about cruises vs. independent travel to the Greek Isles. Cruises are a fine way for people to see many islands with a limited amount of time and without having to unpack their bags. I was only trying to illustrate the many views, opinions and styles of people who travel to Greece. It's not Hawaii.

Has anyone mentioned the Elounda Mare hotel on Crete as a suggested place to stay? It is a member of the Relais & Chateaux hotel organization and is a wonderful, 1st class property that is personal and luxurious. I stayed there 8 years ago and would love to return some day. Be sure you don't confuse it with other "Elounda" hotels; htere are several different properties in the same area.

Meant to include that you can fly into Heraklion on Crete and the hotel will arrange a car service to transfer you to the hotel.

Loved the replies especially the sarcastic ones, having used this board for years I know you must get everyone's attention, I also find it funny when some people claim the board is theirs.

What I always find curious is the polarization...Thats not what travel is about...Who am I or you to judge anyone elses travel preferences

Here is a travel agent that caters to five star families. They will do a good job for you:
http://www.truegreece.com/

Don't let the nasty replies get to you. This ia a wonderful site to get ideas that a travel agent would never think of.

in 2005 I did a 3 week trip to Sicily and Malta (never been there either) and this group gave great ideas and many of the recommendations were 4 and 5 star. We did a blend of 3, 4 and 5 depending on the town, location and time.

I suggest you and your wife by a travel book on Greece, see how big it is, decide how many times you want to unpack and the make a list of things you DO want to do.

Then return to this site for comments on your research. You can also search for trip reports from people who have traveled. Everyone has good ideas and experiences to share. Sometimes your best memory may be from a small 3 start inn with an incredible host. You never know. Better a 5 star meal than a 5 star lodge since you will be out and about anyway.

Good luck