Absolute Newbie

Welcome to YF. Think about a trip to Miami Boat Show. You will get educated in a mind-blowing environment.

What do you plan on doing with the yacht? Cruising areas? Speed? Schedule? How many guests?

This is the fun part because everything is in front of you. Walk the docks. Sniff lots of boats. Get a sense of layout. (I’m a flybridge man myself)

As a fellow midwestern Missourian, baby steps on the Intracoastal Waterway (ICW) around FLL/Miami, Biscayne Bay & Keys are a great start. Then venture north on to Savannah/Charleston. 2nd year pop over to Bimini or West End. Get your Captains license online. Find a great Cap’n who can manage your boat, find you dockage and teach you how to travel.

Living aboard for a few months is challenging to find a Marina, but not impossible.

3 bedrooms (2 nice) and 1 smaller (place for Cap’n or kids) to sleep is the right number.

Don’t get afraid of well maintained older boats.
And get used to estimating everything on the high side and then multiply by 1.5

S Fla is the easiest place to find inventory, has great cruising options, and has no stops from STL.

Good luck.

I hope you have a great adventure. So much fun to be had!

Best input I can give is to really define your needs and intended use as well as where you plan to cruise. It’s easy to get star struck at a boat show. With boats, bigger is not always better. You need to think of things like; how many staterooms/beds, how many heads, how many showers, what kind of weather will you be in, how much range do you need, how much water, cold and dry food storage, what max draft for your intended cruising, do you need stabilized, what’s your comfort level maintaining and fixing systems, what’s your winter storage plans.

I could go on and on but you get the picture. Also consider insurance. Older boats can be difficult to insure and your lack of experience will add some challenges. Yes, hiring a CAPT will help but only so much.

Bigger boats also cost more for moorage and can limit your options.

Not trying to scare you off by any means. Given your background you’ll pick it up very quickly I’m sure. Just trying to give you some tips so you make a great a first purchase and really enjoy it. I’ve seen folks buy the wrong boat and get turned off to boating entirely because of it.

Lastly, there are good brokers and bad ones. Their goal is to make a sale of course. Some are much better at helping you define your needs and working to ensure you purchase correctly. Others are just looking for a quick, easy sell. I’m sure you will spot the difference quickly.

BUSINESS OWNER

I'm putting that in bold so you don't forget it. Why? Because I've seen too many good business persons suddenly forget everything that made them successful when looking at boats. Buying a boat is like every major business decision you've ever made. You carefully figure out your requirements, then you research and find boats that meet those requirements. You look carefully at builders and brokers and enter into any relationship carefully, as you would in business. I've seen the most skeptical non-trusting business persons suddenly fall for a fast sales pitch and shiny boat and question nothing.

My point is that you have the skills, you've long ago figured out how to evaluate new things and where and how to get help when needed. You have a plan for what you hope to accomplish. You know how and when to say "no." You know how to deal with and avoid charlatans and when to evaluate someone as not giving you the whole truth. You've long evaluated, not just products, but companies. You know how to do due diligence so do so.

To get straight to the point, with your flying experience, which seems quite extent given multi engine/instrument...this is good for any voyaging in the future.
I would start by visiting some well known brokerages & walking the docks. See the boats, talk to owners, brokers & especially those that run the boats.
The fact you are not into "high cruise speed" says that perhaps a good quality pilothouse would be perfect. As in 62 to 72 Offshore, Outer Reef, Fleming (if you can find one). If you then decide that the voyage is the essence & not just the destination, then look at brands such as Selene, Nordhavn & other displacement yachts.
At the same time, be open minded & see as many vessels as you can. Judy is right in suggesting the Miami Boat Show as this will be a lot of fun & at the same time offer you different options.
Have no doubt that with your flying & engineering background, you will feel right at home within a short time.

One good option is to charter first. Charter a boat somewhere nice like the Bahamas for a week or so. Just being aboard for that period will give you a feel for what size y0u might need, what size you will be able to manage, and most important, will tell you if you like being aboard a boat underway.

Experience is a huge factor when being rated for insurance. Keep track and start gathering any boating history you may have. Key factors are year, make, model, length of boat and particular years/dates that you owned and/or operated them. More is always better. When I submit a client for insurance I have them complete a boating experience form I attach with their submission. It def helps.

Jim, I’m a fellow STL guy myself. DM if you’d like, maybe grab coffee. I’ll give you my 2 cents as newbie in this whole yachting thing. I’m coming up on 5 years, and still trying to figure it out. Ha ha

I got into boating as a pilot (multi commercial instrument) and I think it is a far bigger advantage than most people realize. Not just because of wx and nav skills but the attitude for lack of a better word. Checklists, quick analysis of conditions, effects of wind on landing whether on a runway or dock, and being aware of the fact that weather flying or boating, you can’t just pull over of the side of the road and call AAA. Well.. yeah a boat can be drifting for a few hours unlike a plane

Sadly insurers may not recognize this ... but your transition will be much smoother than you may think

From a fellow newbie, welcome!

But V1 is. Alway better to be wishing you had then wishing you hadn’t. Good luck!