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Thinking of flying somewhere (ideally north) late winter with the family. Requirements are: Shops for wife, sailboard hire for me, and some fun stuff for the kids to do- and no need for passports. Ideally want to simply get off a plane, hire a car and drive to the final location. Where's somewhere that looks good, is warm, has some shopping and wind? Flatwater, waves, open ocean, don't really care. Just need a holiday!
Cheers for any info 
Easy
Cairns/Green Island/Port Douglas.
Book for the GI Nationals week, Frerace or Slalom M-F. (BYO Windy Gear)
Family can come to the island some days (very sheltered in close) whilst you sail in the wind zone, stay on the island or main land.
Heaps to do on main land, shops, food, restaurants, cafes bars, Day Spas's, movies, cable ski, mountain bike, rainforest, rain forest cable car, train ride to baron falls, Port Douglas is nice also, Barron falls, whitewater rafting, windsurfing GI, Kitesurfing Port Douglas, SUP, Sailing, Reef Diving Snorkelling , Fishing, Casino, Horesriding, Motor bike riding..etc etc etc
+1 Green Island/Cairns. As mentioned they are having Nationals there again this year. It is probably one of the best places in Aus over winter for consistent wind and warm, as the trades are generally pretty good throughout winter.
It is only 30 min ferry ride from Cairns, so if you want to actually drive to the destination you may need a Bond Lotus
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Shopping around Cairns and plenty activities near Cairns for the kids. Could always stay at Trinity beach (nice for the Fam.) to the north and windsurf near there or Yorkeys Knob (if you really want) not that far away from Cairns. But I think GI is by far best spot to windsurf. The land can afffect the wind near the coast so you have to head a fair way out on the mainland depending on wind.
GI is windsurfable flat water blasting most days and some chop hop further out. Toody on Green Island did do hire last year at a reasonable rate and good gear but you would need to make some enquiries.
Just returned home from Port Douglas, with wife and 2yo daughter. A magic, hassle free holiday with some of, if not the best sailing I've had in my two years windsurfing.
Flying Qantas really made It easy. I was able to use my, and, as 2 year olds require their own ticket, my daughter's checked baggage allowance for my gear. 1 bag with 2 race sails and 1 mast, and the other with my 122 board, boom, harness, extension, fins, and some fill e.g - clothes. My gear didn't make it on the plane on the way up, but was delivered to my door in Port Douglas the next day!...undamaged
This left myself and my daughter with 7kg of carry-on each, heaps, if you can wash whilst away.
Port Douglas was great for relaxing and eating and not bad for shopping either. Not a lot for the kids, but the Daintree was a great day trip, as was Kurranda and Mossman Gorge. We spent no time in Cairns but looks good also and only an hour down the road. Ports local sailors are very friendly, and are very helpful if you need help with local knowlege or gear, like spare lines, thanks Ed 
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Pretty much bump and jump at Port, but yes, GI is an easy day trip giving 5 hours on the island for $86 per adult. You can stay on the island also!
We will definitely return for more.
Good luck.
Granted, Hawaii would be great, but trying it with kids?, the flight might not be that fantastic
. No need for passports was also mentioned.
My mate just got back from Maui and loved it, he took the whole family including kids 3 and 5. They all had a great time and the windsurfing is not fair. Steady 30 knots nearly every day and a choice of flat or waves within sailing distance. The only thing I have against that suggestion is jealousy.
By the way the shopping is not bad for the windsurfer either. He brought back a nice Kode 103 carbon pretty cheap
If you can't afford Maui or it is too far then Cairns is pretty good. I have stayed at Port Douglas and travelled to GI. I windsurfed right from my back door at Port Douglas but the brownish water full of debris and fear of Crocs makes GI much nicer. I think the water color changes depending on conditions. I prefer closer to Cairns but Port Douglas is as mentioned a nice spot for the family. By the way I also took heaps of gear (QANTAS), make sure it's an A330 or 787 if Jetstar not smaller planes. Also, I used the hire gear on Green Island for simplicity.
The fly to Cairns, stay up Port Douglas way, then head back to Cains and scoot out to Green Island for a few nights might be a winner. Hard to please eveyone, and I can't handle the endless "Are we there yet?" chant of doing trips that are too long range. So FNQ it may well be. Cheers for all the info.
Maui definitely, kids, no prob, a million things for them to do, been there done that. My daughter got many great memories that lasts forever, above and below water, highly recommended. Try to hit the non-summer season with them, just before, or just after their summer, not so crowded, and better prices.
Maui +1
Great family holiday destination for younger kiddies
Happy kids
Happy wife
=
Happy life
and the bonus is windsurfing everyday and being able to see some of the sports best at work out at Hookipa in the waves or round the corner past the airport for flat water blasting
