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If it helps at all we were in the same situation as you about 4 years ago.
We were in the UK, just retired at the same age, modest income and sold everything to buy a boat.
We have now been living aboard and sailing for the last three years and the only thing we regret is that we did not do it sooner. It is an amazing life and if we can advise in any way then please just contact us.
Our website is below with regular blogs, photos and an idea of what this living aboard life is really like.
Cygnus III | How not to cruise around the world in a sailing yacht
 

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That's great thanks for the positive tilt on this. Looking at a lot of the posts on live aboard matters there does appear to be quite a lot of negativity about the idea. We were just starting to wonder why people were actually doing it at all! Love the web site, great idea and what a great way to preserve those memories! Do you tend to spend most of your time in the Med?
I am presuming here that you are replying to us.
The website is like a diary to us as otherwise you will find that all the wonderful places you visit and people you meet get a little mixed up.
Besides we enjoy writing the blogs and having some fun on them.

We have never planned more than a few days in advance all the way down. If the weather is right, If we feel like moving on or staying longer we do. We never know if we are turning left or right until the wind tells us so. If you don't make plans then you cannot fail at them. We will just keep going as long as we can and decide where next on a whim.
 

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There are other things to consider that worked for us but obviously may be different for you.
We bought the boat in October and even with an excellent survey we still needed to make various changes to make the boat ready for world cruising as we did not know when we would be back.
We used the winter period in the UK to do this . Chandler's are cheaper there than the rest of Europe.
There are friends and family to say goodbye to as well.
It also gave us chance to become accustomed to our new boat/ home and get to know all the systems before setting out.

Don't under estimate the change from bricks and mortar and a working life to one aboard a boat. We have met many cruisers and can say from personal experience that the man will adapt quiet quickly but it is sometimes harder for the woman. They are leaving behind jobs, family, friends, the life they built behind and are alone again for the first time in a long time.
My wife had real problems to start with. Luckily Europe is easy for her to fly back to the UK so she always could do it if she felt the need. It really helped.

Now after three years she really does love the life and is so happy. She still misses friends and family but would not change for anything.
 
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