Yachting Live-aboard...in about 5 yrs.

We retired, sold everything, and moved aboard 4 years ago. We have been boaters for decades, spending weekends aboard; so living aboard wasn't new to us. Being retired, and being in Florida [we're from Tennessee] was new, and required some adjustment. All said, I wouldn't change a thing.

My wife and I did something very similar 5 years ago. No experience at all and chucked everything and did a full two years up and down the east coast. Learned a LOT before jumping in and during the whole adventure.
If you have never owned a "big" boat before, insurance will be your biggest hurdle. If you have time and the means, I would start now by buying a smaller boat to learn on so that you are not faced with the insurance company demanding that you use a captain for the first year.
We were very lucky and bypassed this with some good training and a sympathetic insurance agent. Our first boat was a 55' Neptunus and it was a great boat for our purposes.

A number of pilots live near us in the Keys; MIA is just 2 hours away [depending on traffic, there's just 1 road down here]. I'd do what Jimmi suggests and get as big a boat you can manage in your area; take classes from the USCGAux and Power Squadron; if possible, take a captain's course from Sea School. The more experience you have the easier the boating part will be for your move. As for living aboard, look at the creature comforts that you have and determine what are "must haves". All boats are compromises; just make sure that what you give up isn't something that you'll need to make life aboard enjoyable. For us, we had to have an on-board washer/dryer, satellite TV, a big enough galley for the Admiral, sufficient head/holding tank so the Admiral wouldn't have to use a shoreside toilet/shower, and a king size bed. It will take you a while to figure out what your essentials are.

Make sure you keep a log of all training that you take. Date, hours, subject etc. Count everything, even maintenance courses etc at boat shows. If you go out on a friends boat, log it as training as well. If you have a comprehensive log that you can offer the insurance company it will help (it did for us). Power squadron courses, boat safety courses, diesel or other mechanical maintenance courses. We basically provided a complete resume.

Search for "Yachting for Newbies" in this forum. I put together a lot of the basics for this type of situation.

The longest I've lived aboard was 60 days. But several things I find crucial. The shower and head, size of holding tank, comfort of the stateroom, lack of noise, being able to walk around without a bunch of steps everywhere, a galley and refrigerator that are usable and not tiny.

Neither of those boats mentioned would I want to live aboard for any time. A Hatteras 60 MY, would be ideal in that size range. Quality boat, very large salon and galley and master stateroom, very large flybridge with enclosure and air conditioning, nice aft deck table etc.

My wife and I raised our 4 kids living aboard since 2012. At first, we had the exact same plan as you... live aboard once we had an empty nest. But, since our kids were always involved in boating with us and some of the best experiences we had were always on boats we asked "why wait?" Yes, it is absolutely financially stupid, but buying a boat and living aboard has been the best decision we made as a family. The memories and lifestyle and bond we made together in the past 7 years is amazing. Life throws us curve-balls. Money comes and goes, memories can't be taken away. Enjoy it while you can!

I agree with just about all the points made above. When we were boat shopping some of the priorities were: Real fridge/galley/appliances. Washer/dryer onboard so you aren't always using the marina laundry. Real bath/shower. Flush deck so you aren't up/down steps all day. Master berth area separate from other berth area (the most privacy from kids or in your case guests). Reliable functioning head/waste holding tank so you aren't walking to the marina bathrooms. King size bed. Real salon furniture instead of the 3/4 scale built-in stuff you find on a lot of boats. Closet space! Accessible/serviceable machinery separate from the living area (for example; not having to remove the salon floor to do engine maintenance... hah!). If the boat is equipped with appliances or "things" that look like they belong on an RV or a Searay... nope. Function before form!

Although the common train of thought is "buy the smallest boat you can feel comfortable in" I see very little disadvantage to a slightly larger boat and many disadvantages to a smaller boat for a full time liveaboard. You don't want to feel like you are camping. I'm not saying a larger boat is better, but just don't be afraid of looking at a slightly larger boat than you think you will need.

Figure out what kind of cruising you will do and what kind of range you will need. Like captainwjm said above, all boats are compromises. We started looking at bigger boats around 2010 and found our boat in 2012. We looked at mostly older vintage Hatteras MY, Chris Craft, Burgers and even some Vikings... but ended up with something a bit "different" that ticked all the boxes with some compromises we can live with.

Having lived aboard for six months at a time, there are lots of things you need to consider. We lived on a 46 foot sailboat in a couple of really good live aboard marinas. Where you will be living, if you stay in one place for a period of time, will have a major impact on what boat will work for you. For example, the quality of the air conditioning was much less important for us when in Connecticut than it was in Florida. Outdoor living space importance also differs from place to place.

I would second the comments about a larger boat if you can handle it even though it adds costs. My wife still claims that the reason we spent so much time living on the boat was to make sure that when we sold our 5 bedroom house and bought a condo, she would be very happy with the size of the condo. The ability for each of you to have a place to sit, work, read, etc without being together 24/7 often means you need a little more boat.

As we all get older, you also have to think a bit about making sure that you can navigate the interior of the boat even if you have a sprained ankle. Our Sabre 45 powerboat minimizes the number of steps but our sailboat had a wicked ladder to the cockpit. Just one more thing to consider.

Most of all, do it while you are young enough to enjoy it.

Hello everyone, to continue the theme of "doing it while young or healthy enough".
I have little experience with big boats except when I escape from Vietnam on a 36 ft fishing boat. I have small bow-rider when young in the U.S.

My wife was diag with stage 4 lung cancer recently, not operable. she is doing chemo monthly. I'm 51, she's 60. She wants to be on the water and cruising, I do too. we have enough to retire from work to live her wishes. I'm looking at high 40fts to low 50fts 2 or 3 cabn, 2 hds. I have research online and walk on tour of several boats hatter, searay, azimut, and have come to the decision about layouts. large cockpit flush deck, cabins under is fine, molded steps to flybridge and galley up. What I need to do now is to do a series of rd trips to see as many boats with those characteristic. Are there any retired experienced boaters here that is willing to go on these trips with me on my dime. I pick u up do the trip food and hotels paid by me. I have set a goal of getting my wife on boat in 4 months and figure will have 2 years until she won't be able to enjoy it. please let me know if anyone can help. We are in Ga and want to look for boats from Florida up to Maryland maybe the Great lakes.

Thank you
Nam

Hi Nam. As a 4 time survivor I tell your wife Good for her. We're old the day before we die at whatever age. Live your life fully right up until that day.
The first thing you need do is narrow down your budget. Even in the mid-40 to mid-50' range you're talking anywhere from $100K to $1.5M. Also consider that you'll probably need to have a captain aboard for the 1st year, especially once you go over 50'. That's expensive. Separate out your shopping budget (how much you can spend traveling around boat shopping), the purchase budget (price of boat you're looking for including refit costs) and your cruising budget (what you can afford to spend on maintenance and repairs, fuel costs, local and transient dockage, etc.). As much as you want to make every day your wife has special I'm sure she wants to know that her family will be secure after she's gone.
Next consider where you want to cruise. Are you looking to do extensive ocean travels or staying in more protected waters like the ICW or Great Lakes?
There's lots more considerations, but that should give you a good starting point.