Thanks everyone to take the time to share your experiences.
Let me try to explain my situation and the reason to get into sailing.
I've been triying to have the sailing experience since I was 30. Familiy, kids, etc stopped me (I stopped myself). Now I'm 50 and my son and daughter are independent so I think is the right moment.
On the other hand, this year my life kinda turn upside down with this worldwide casedemic. I don't know you guys, but I don't want to get trap on a quarantine concentration camp or to be forced to get a poisoned vaccine. Before this, I was dreaming about sailing freely from port to port, ,,, now I'm not sure about that would be possible. Every country is taking draconian/dictatorial meassure against citizens and traveling from country to country I think is not going to be like it was.
I did my dayskipper few years ago in UK, unfortunately I didn't continue sailing so I forgot pretty much everything, so I need to refresh it.
My plan is during the next Oct/Nov to get a charter with a good skipper for few weeks, or as many weeks need it to get a decent understanding of sailing (like a private lesson), then I'll start to search for a sailing boat. I am in Italy right now but I think we will expend the winter in Greece and during that time I'll be checking on possible boats to buy.
Choosing the right boat isn't easy at all. We want to get a blue water cruiser, we want to do mediterranean and caribe if we can. Too many options and very little knowledge from our side to decide the right one. So I though that it could be an option to pay somebody to help us to choose the boat. First we though about getting a 20K eur boat, just to learn and see if we like it but I know that if we like to sail we will want to get a bigger and better boat and selling the boat is going to be a pain for sure, so maybe is better to buy a boat that has the right specs.. I see 40-50K boat that looks good. Obviously I'll get a survey on the boat before buying..
So going back to the begining my concern is with the situation that we are facing in every country and expecting to continue like this with more lockdowns, do you guys think that life will be harder living in a boat than living in a country house?
My reply to chicory83
Are you planning to work or are you retired?
I am not planing to work, just try to make enough money with my investments
What kind of space do you need to live happily with two people aboard?
after checking on many boats, around 40' seems to be the right one
Do you want to stay in one place or move around?
We want to move around, from continent to continent.
How important is it for you to be near friends and family?
at this time we are not conditioned for that
What are your shore side transportation and storage needs if any?
we want to travel as light as possible, so I'll be selling or giving away everything
What kind of health care access do you need?
Fortunately we still ok, but we probably will need to get some kind of insurance at some point
What kind of exercise do you need to stay healthy?
We like to do crossfit, montainbike, ... is going to be hard if we are sailing!
Do you have the skills or mechanical ability to repair and maintain a boat?
I can consider myself handyman so I am good with tools, electrics, etc
Can you afford to maintain your boat?
If we are talking about light repairs, TLC, probably with a little info I'll probably be able to do it myself. If we are talking about big jobs probably I'm not capable to do it. At this time I do have some money to fix some mayor dissaster.
Do you have time and patience to deal with the added complexity of everything from grocery shopping to laundry to personal hygiene concerns?
Sure, we can do that