Is this feasible?

Absolutely, but spend the time with good people getting the lessons.
RYA scheme works best

Abso-bloody-lutley it is feasible.

I have been around boats all my life too, but mainly the powerboats. I did have a Catalina 28 for a little while but it spent most of its time in the pen. Two years ago now I bought a 47 footer in Brisbane with the intention of bringing her home to Perth. I had previously done RYA training, done a few bareboat charters in the Whitsundays and helped very, very rarely crew a boat, plus a total of 5 one day trips on my new boat before heading off for a 6 month sail. So I was considered fairly much a Greenhorn and I was the most experienced on the boat.

So from first hand experience, this is what I learnt.

1. Ask questions. Do not be afraid to ask anybody and everybody. There is no room from pride here. Ask people you meet, and ask people on this forum.

2. Don't be afraid to ask for help. On at least two occasions on the east coast in sh!tty weather we decided to make for a marina instead of our desired anchorage. My family (wife and two boys under 10) were new to sailing and if they felt safer in a marina then I wasn't going to argue wth them. We asked for help coming into the docks and held off until it was available. But nearly everywhere we went unsolicited help was offered. We usually accepted it. A solo sailer that spend a few months sailing along with us was always asking for help and advice. She is now in Trinidad.

Don't discount mental and psychological help either. After 4 1/2 months and 4 weeks of that belting into 20-30 kts southerlies down the west coat (funny how that wind didn't bother us up the east coast), we were spent. Close to home but so far away still. We asked FreeRadical (from this site) to help us for a Week. FreeRadical flew from Perth to Shark Bay and spent a week with us sailing to the Abrolhos Is then to Geraldton before he had to fly back to Perth. The weather did improve and we had a nice time. But I don't think FreeRadical has any idea on how much he lifted our morale and spirits.

3. Safety First. Know your limits. Often comfort limits are reached before physical limits. Stop when the comfort limits are reached and slowly but surely they will expand. If you have to ask the question, you already have the answer eg, Should I reef... Reef. Should I put on a life Jacket.... Put on a life jacket. Be prepared to leave a beautiful anchorage early is needed for weather, but conversely be prepared to stay in a crappy one longer if required too.

You will start out with a bag full of luck and an empty bag of experience.
The trick is to fill the bag full experience before you empty the bag from all its luck

4. Are you sailing with young kids and do you want them to enjoy it? If the answer is Yes, then on your boat you don't have winches, halyards, sheets, clutches, pulpits, pushpits or any other of these items. What you do have is.... That round silver thing, the white rope with the black fleck, or the green rope with the white fleck. A bunk is a bed, a head is a toilet and the galley is the kitchen. They will be to overwhelmed as it is to remember outdated and irrelevant terms. My two (now 12 and 9) started to understand and enjoy the sailing once I realised this and now call everything by the said outdated and irrelevant terms and we are a well oiled machine.

5. And you will be ok if you can follow my golden rule:
Stay on boat
Keep water off boat
Keep boat off land.

Sorry for the long winded post. Once I got typing I couldn't stop. The rules and suggestions above are just commonsense really. Don't let anybody tell you that it is not feasible. But just do it (with the proper preparations). You won't regret it.

Thinking of a Top Hat then go to and join

http:/www.tophatyachts.com

There you can contact Top Hat owners who may take you on and as well there are Top Hats for sale right now.

My first [and only] yacht is a Top Hat [SV SEAKA] and there isn't a better yacht to learn in or cruise if your funds are limited.

Another reply here that its totally do-able.
Your nearly half way there having a general idea about weather, and common sense. The hardest part will be getting to the day you actually leave, the rest is easy.
I left Port Bundaberg this morning and hada fantastic sail, currently anchored behind Big Woody Island in the Great Sandy Strait, in a Top Hat 25,southbound after going to the Whitsundays. Its been a brilliant trip, i have enjoyed it and loved every second.
I have been sailing in company with a couple of other single handers since Shaw Is, which is awesome fun. One in a S&S34 and another ina Mottle 33, and the little TH has not been disgracing herself, very little distance between us at the destination

And another invite for a ride out on PPB with me on my Compass 28 (sort of like a TH's bigger brother) out of Sandringham.

Take up all these offers, be hungry for experience, sail a lot before you buy anything.

Cheers, Graeme

Thanks so much for the support and warm welcome. I'll definitely be taking up those offers to other's boats and really appreciate the generosity. Its exciting to know that it can be done. Time to put the plan into action!

You read stories about people with no boating experience buying a boat, getting a 3-4 hours lesson from the owner and off they go. And they manage.

Since you have some boating experience, you do know a thing or two, which is a big plus.
Sailing is relatively easy but compared to a tinnie it is much much involved in every way.

Ton of good advice in the comments above, remember practice makes perfect and nobody is perfect at the start.
And there is no such a thing that too old for something.

Everything is relative. I had known people, who owned boats for years, yet rarely took their boats out and called themselves experienced. Than there is this other guy, who was only boating for 6 months but he was out every 3 days. They called him a novice. Who do you think had more experience?

Also, read articles and watch you-tube how to videos. Not everything is gold, but it certainly will broaden your knowledge. Nothing beats hands on and experience, so just do it and sail away!