Absolute Newbie

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!

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.

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

From a fellow newbie, welcome!

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