Congrats on the award tickets and turning 40! I am not an Australia expert but we did a DIY trip a few years back and can give you some insight into what we found.

We did 11 days in Australia in November 2008 - 2 nights 1 day in Melbourne, then drove from there to Monrington Peninsula, Great Ocean Road, Cape Otway, Grampians National Park, and McLaren Vale (wine country), then flew from Adelaide to Sydney and spent 5 days in Sydney.

Sydney was glorious - a sexy, vibrant, lively international city. Five days was perfect for us - we spent two days in a boutique hotel in the city center and three at Ravesi's on Bondi beach. The weather did not cooperate (you will have much more beachy weather) but we were never bored. Just a wonderful city.

Melbourne was much more laid back. I think 3 days tops should do it (although many others will disagree). One and a half days was more than enough for us actually.

We did not do the Great Barrier Reef or the Blue Mountains so I cannot comment on that.

I will tell you that we had an amazing trip from Adelaide to Melbourne. I will explain what we did backwards.

Adelaide Airport to McLaren Vale (Wine country). We stayed at B&B in MacLaren Vale (two days). Visited some wineries, including the glorious Coriole winery that does a fantastic and affordable lunch on Friday afternoons.

McLaren Vale to Dunkeld (Grampians National park). Stayed at the fantastic Royal Mail Hotel and ate at their award winning restaurant. We just stayed one night to ennjoy the scenery.
http://www.visitvictoria.com/Regions/Grampians/Destinations/Dunkeld.aspx but could have easily spent a lot more time.

Before that we stayed at The Great Ocean Ecolodge in Cape Otway. Run by conservationists, with alittle animal hospital, they will take you on a tour of the reserve to see wildlife in its natural habitat. Plus they have loads of kangaroos bouncing around the property. One of the most unique and amazing places I have ever stayed. Easy to get to off of the Great Ocean Road. http://www.greatoceanecolodge.com/

Before that we drove the great ocean road, starting in the Mornington peninsula south of Melbourne. I believe that's where you can see the penguins. We stayed at the Portsea Hotel http://www.visitvictoria.com/regions/Mornington-Peninsula/Accommodation/Hotels/The-Portsea-Hotel.aspx
and loved it. Very homey - like an aunt's guest bedroom in Cape Cod.

Our trip from Melbourne to Adelaide (via McLaren Vale, the Grampians, Cape Otway, Great Ocean Road, and Mornington Peninsula) took about six days and felt a bit rushed. It was still fun but we spent a lot of time on the road. Driving in Australia takes a lot longer than the quoted driving times plus it is kind of stressful - long stretches without signs. Lots of rotaries and you are on a different side of the road. But we had a marvelous time.

Hope that helps.

Thanks, UserName! I was definitely looking into staying at Cape Otway for one or two nights before. I should probably revisit their site soon as I know they don't have many rooms there.

Hmmm, so an idea might be - do Sydney for a few days, then fly to CNS for the Great Barrier Reef/Daintree stuff, then fly from CNS to ADL (but would probably have to connect in Syd, which would suck but oh well), and THEN renting a car in Adelaide and doing something similar to your itinerary backwards, getting us back to Melbourne by March 3rd!

I would definitely check with the experts around here about time management but I think 3 days in Sydney, 5 days in the GB reef area, then 7 days from Adelaide to Melbourne (ending in Melbourne) sounds doable.

Accomodation at the Ecolodge is extremely limited - we basically planned our trip around the one night we were able to book there! But it was so so worth it. The young couple who run the place (and built it) are national treasures.

I'm not sure I fully understand your flight arrangements. Presumably, you're flying CX ORD-HKG-SIN (which are not A380 flights) and then taking the QF A380 flight from SIN-SYD?

The period you have in the middle (2/23 - 3/3) presumably covers the trip up to Cairns and the GBR. I would fly SYD-CNS and then CNS-MEL. I wouldn't try to fit in another destination unless you really, really want to (and it sounds like you don't). The amount of time in Sydney, Cairns and Melbourne can presumably be adjusted once you finalize what you want to do.

When you go to Cairns, stay in Palm Cove or Port Douglas, rather than Cairns itself which, in my view, has little to recommend it.

For Melbourne, you can take a couple of days and drive the GOR. Either pick up a car at the airport when you arrive and do it straight away or take a couple of days in the middle to do it.
http://www.visitvictoria.com/Regions/Great-Ocean-Road.aspx

If you want some wineries, visit the Yarra Valley, an easy day out from Melbourne. If that's of interest, specific wineries can be suggested and several wineries can provide a good lunch.
http://www.visitvictoria.com/Regions/Yarra-Valley-and-Dandenong-Ranges.aspx

You might also want to think about a day or two in Daylesford, the spa capital of Victoria. It's an easy hour and a half drive from Melbourne. If you're in that part of the world, consider visiting Bendigo and Ballarat.
http://www.visitvictoria.com/Regions/Daylesford-and-the-Macedon-Ranges.aspx
http://www.visitvictoria.com/Regions/Goldfields.aspx

As for Phillip Island, to each their own! I live here and have never had the slightest inclination to drive 2 hours to watch a bunch of penguins come ashore but lots of people seem to like it.

There are any number of threads around here with more information on what to see and do in Melbourne (and Sydney) so I won't repeat them. However, if you have questions, please ask ....

You're right TT7, the Cathay flights are not A380... I think it's a 747. Just the Qantas part is the 380. I'm functioning on only two hours of sleep and got that part screwed up.

Enjoy your flights! I did LAX-SYD/MEL-LAX on the A380 in first for my 40th b-day this year and am totally spoiled now. How can I ever go back to business? Make sure Qantas has your contact information if you want to book a spa treatment in the MEL first lounge. The lounge hosts will contact you the day before your flight to schedule. Enjoy the Park Hyatt in Sydney too! We stayed at the Marriott this time just for something different which was fine but I was really kicking myself for not staying at the Park Hyatt again.

I think either 3 or 4 locations would work depending on how you normally like to pace your vacations. Our first trip was a bit of a whirlwind and we went to Cairns, Tasmania, Adelaide, Kangaroo Island and Sydney over 16 nights. I felt the pacing was fine and am glad we got to experience all of those places. I fell in love with Tasmania so that's where we spent most of our time on this last trip but I'm more of a nature/wildlife person though I do enjoy cities as well. Kangaroo Island and Tasmania are excellent for wildlife so are the Atherton Tablelands outside of Cairns. I'm just not sure about the weather at that time of year as both of our trips were in the winter.

Good luck with your plans!

Since you're flying via Singapore, you should come on over to Perth! Only five hours from Singapore!

We have loads of wineries, plenty of unique animals, brillaint beaches and coastline, massive trees in the spectacular SW and the world's biggest rock - Mt Augustus, which is two and a half times bigger than Uluru!

Okay, just read that you'll be here in February, so scratch that. WA is ungodly hot in Feb.

jenblase,
Congratulations on the award tickets.

With regards to Cairns, reef and rainforest: as that time is not any kind of peak and schools have returned there will not be a need to book ahead. I suggest you keep an eye on the weather and book accordingly for the reef and fill in the other time with the rainforest. What do you want to see in the rainforest: Platypus, Tree-kangaroos, bower-birds, ancient plants? If the last then head for the Daintree area and cross the river, for any of the others or the endemic mammals of the region it is best to go into the mountains and the Atherton Tablelands is the spot to do that.

Some good coffee and cheese places up in the mountains too.

I'm not sure that the flight from ORD to SYDNEY will include a stopover in Singapore - Hong Kong is Cathay's hub city.

I personally would recommend SYD- CNS, then CNS-MEL. I don't think it would be a good idea to fly to ADE and drive across to MEL...it's a big country, distances are vast, that's why the poster above said that driving from Adelaide to Melbourne in 6 days felt a bit rushed.
I agree with tt7's...stay in Port Douglas or Palm Cove, the latter would be my choice but Port Douglas is bigger and have more shops, but both very nice IMHO. The Daintree is beautiful, you might spot a cassowary in the wild if you are lucky! The Atherton tableland is marvellous also.
Pick up car from MEL and drive to GOR, easily achievable as the MEL airport is on the west side of the city so you don't have to worry about traffic driving across the city. There is a lot to see along the GOR and the region warrants a few days...there are numerous walks in the Otway national Park (you can do the multi-day great ocean walk which would be so beautiful in Feb - google for info, you can join a group or do self-guided), visit the shipwreck coast plus there is a farmers market in Apollo Bay every saturday. Any days left over I would do day trips out of Melbourne, as already suggested - Daylesford or the Yarra Valley. Good luck and have a great trip!

If I can suggest 1 thing, do NOT use Greyhound (bus company) for your travel - I used them because I was in a remote part of Australia, and when I asked the driver about my connection, he told me to get off at the wrong city and left me there... So I had to spend the night there and wait for the next bus the day after, and the company doesn't even want to refund my ticket or the price I had to pay for the room ($50)...

Since flights are quite cheap, I would definitely go by air, especially if you don't have too much luggage to carry - try Jetstar, Virgin Air, Quantas. They always have "last minute sales" and you can usually get around for less than $100 per flight If you do have to use a bus company, use Murray's coaches. You can also hire a van (wickedvans.com.au) or a car, but petrol costs quite a lot.

Melbourne is a great city with lots of personality, and the Great Ocean Road is very scenic, if you do come down south in Victoria.

Have an awesome trip!