See Seeking Advice. Add this to the question.

"My current thinking is to play around in the Caribbean again for a while then perhaps over towards Central America. Pleasure boating experience is nil. Some deck experience when on the Navy ships."

Important self-reflection on boating experience being nil. That's central, IMO.

You're coming to boating like we did, later in life. (The navy experience, while formative, isn't quite the same as owning a little fiberglass boat.)

As with all things nautical, there's a balance here. A sailboat lives between the aerodynamic forces pushing her over and the hydrodynamic forces that permit forward motion. When sailing requires people, then the dynamics of the crew is a lot like the dynamics of wind and water. There's a balance point there, and not everyone can find it.

Starting late means learning faster. Preparation is an individual thing, but it's also a balance between who owns what roles.

CA and I started this journey in 1998. While that's a long time ago, it's also a later-in-life kind of thing. I bought my first boat at age 42. First. Prior to that I had spent only a few hours on boats going to and from SCUBA destinations. A few hours on the Finestkind (https://www.finestkindcruises.com) in Maine. The Cape May-Lewes Ferry. A fun outing on classic America's Cup sailboats in Narraganset bay. My boating experience was essentially nil, also.

Talking with folks who grew up on or around boats is helpful. But, for those of us coming to boating later in life, we can't follow their path. We're forced to find a different approach that optimizes speed of learning, without getting knocked over by an unexpected gust of wind or a splash of wake from a crossing boat.

How do we go from essentially no useful experience to living aboard? For CA and I, it seemed to work like this:

• Armchair Sailing

• Training

• Small boat

• Chartering

• The Jump

I sail into each of these bays and check their depths and plot some landmarks.

Sailing Far in the Living Room

This isn't hands-on sailing. But. I started as an avid armchair sailor. Stacks of books. Fiction and non-fiction. Does it help? I think so.

I read aloud to CA. Have read aloud for decades. Some good books and some bad. I act it all out. I do voices. We discuss. Some of my choices were bad. Some were good. Currently, I'm reading S. A. Chakraborty's City of Brass. Before that it was N. K. Jemisin's Broken Earth trilogy.

Sailing books included Suzanne Geisemann's first book, Living a Dream. (http://libertysails.com) I'm not sure I can recommend other titles, but this was helpful.

Fastnet Force 10. Unpleasant but also helpful.

The Hal Roth's Seafaring Trilogy is brilliant writing. Some of the best there is.

The live-aboard cruising books are a lot more useful and interesting than the heroic adventure books. Beth Leonard's Blue Horizons, for example, doesn't have a lot scary-situation heroism. It has a lot of planning and pragmatism. Indeed, all of Beth Leonard's writing was helpful for us.

You get the idea. Back in the olden days when print magazines were a thing, we had Cruising World and Sail magazine delivered to our house. Plus Practical Sailor for a year or two. Ocean Navigator for a year, I think.

All of the "sail off into the sunset" books are fun. Not all of them are helpful.

There are several galley companion books that explain how cooking on a limited energy budget with limited refrigeration works. My partner loved this. Absolutely fell in love with the idea of optimizing energy use while cooking well. Adopted using a pressure cooker years before we bought a boat. Almost everything we've eaten for at least the last 15 years is a pressure-cooker modified recipe. It's simply more efficient, and requires creativity to explore the opportunities.

Training

Sailboats are tricky things. I would not put anyone on a sailboat without a fair amount of hands-on training under the watchful eye of someone who knows what they're doing. Powerboats — as long as the engine starts — are considerably simpler.

For sailing, it seems like ASA https://asa.com/learn-to-sail/ is a good choice. USSailing is a little more geared toward competition. They do have a recreational program, but I never participated.

We took several courses at several different times. A YMCA learn-to-sail on small boats. A PSIA learn-to-sail on a bigger boat in San Diego in 2000 — essentially a skippered charter. The ASA 101-102 combination course in Rock Hall, Maryland in 2003. And, a skippered charter in the Tampa Bay area. Really a kind of long weekend on a boat.

After the PSIA class, we were ready to go on our own in a bigger boat. We continued to take other classes to move beyond simply sailing toward cruising. Living aboard is a bit more difficult than day sailing. The additional skills of monitoring consumables, and understanding the weather were important. Troubleshooting problems is big.

Small Boat

In '98 I bought a Chrysler Buccaneer. It's a racing boat. Was this necessary? Maybe. It taught us some skills, some of which are applicable to our current very large boat. It also showed us who we are as sailors. Could we maintain a boat? Did we like the places we could go?

At first it was craziness. CA wanted no part of it. But family time was a good thing, and the more we learned, the less terror it held.

Small boats are tender. Finding the balance between wind and water is hard. Who sits where. What the ropey thing does. How the wind shifts across a lake. What happens when you tack or gybe. When you fail to find the balance point, you tip them over. It's an "involuntary swim break." It can be scary and unpleasant; but that's sailboating. After a while, you don't tip them as much. Then you don't tip them at all. Then you wonder how you could have made that kind of mistake.

Powerboating is going to be different because they're not as tender as a sailboat. In many places, powerboat day rentals require essentially no experience. Where sailboat day rentals require some evidence of experience and skill (i.e., a sailing resume.)

Chartering

We did several week-long charters. Our 25th wedding anniversary was a week on a charterboat in the BVI's. This was 2007, so we'd been sailing for almost ten years on the little racing boat and and we'd been taking different cruising training courses on and off for almost seven years.

While not obvious at the time, we were looking for a new balance point.

Part of the trip answered the question, "Do we want to commit to this? Or do we want to continue to charter?"

We'd been chartering for years. In 2004 and 2006, we'd chartered a 30' sloop in Lake Champlain for week. Provisioned. Sailed around. Anchored in random places. We knew we had the skills.

The trip to the BVI amplified the answer to a resounding "Yes."

One of the big reasons why it was a resounding "yes" was the number of unknowns. Not everyone likes sailing into the unknown. It turns out, we liked it. In particular, sailing to Anegada was a scary and successful day. You can see almost all the BVI — it's volcanic caldera filled with ocean. You can't see Anegada: it's low, flat reef raised up a few feet above sea level. It's proper old-school compass navigation. Can you steer by the compass? Do you understand the chart?

Are you comfortable with this? Is there where you're finding balance? We did.

The Jump

In 2009, we sold the suburban house and moved to Norfolk, VA. This is a HUGE jump from house to boat. Not everyone is willing or able to do this.

For a lot of people, home equity is all the money they have. Selling a house to buy a boat destroys that equity. Period. A boat has no ROI. It is a hole in the ocean into which you throw money. Real property can often have a positive return. (There are complex politics behind housing stock and zoning and related issues that can prop up valuations artificially. That aside, a boat carries a price tag like real estate but no ROI.)

We'd chartered. We'd looked at boats casually.

When we started looking, we weren't totally clear on what — precisely — we were looking for. If we'd been super-duper careful, we might have stayed with a 34′ or maybe 36′ sloop. Instead, we went for a 42′ ketch, a dramatically different kind of boat.

Lots of folks move through 10′ jumps in 5- to 10-year intervals. An 18′ racing boat to a 28′ day sailor to a 38′ cruiser. Each step adds skills, boat systems, and complexity at a sensible pace. Each step is a measured change, a gentle increase in wind and wave height.

We went from an 18′ racer to a 42′ boat capable of circumnavigation. Jump.

We spent three years rebuilding parts of the boat, day-sailing, and figuring things out before we finally departed for a two year cruise down to Florida and the Bahamas, up to Annapolis, back to Florida, and then back to Deltaville, VA. I'd guess that it was about 4,000 miles.

tl;dr

I'd suggest the reading - training - chartering as three essentials. Owning a smaller boat may have been helpful, or may not. This seems to vary a lot. It depends on the balance between the various crew-members.

For most of the ten years we had the racing dinghy, I handled tiller and mainsheet. Guests (or one of the kids, or CA) would handle the jib.

The last year we had a fine day, and I offered CA the tiller. Keeping track of tiller and mainsheet can be very tricky. You're driving through a crowded lake and also optimizing the wind. It's a big jump.

Throughout the afternoon she began hauling in the mainsheet harder and harder, and pointing us higher and higher into the wind. This combination provides huge speed, but also makes a sailboat heel. The skipper and crew need to hike out to counterbalance the force on the sail. A little more mainsheet trim means a little more hiking and a little more speed.

To a limit.

If you go too close to the wind, the sail can lose it's aerodynamic shape and start luffing like a flag. On a big boat, the transition is gradual. On a small boat, it's often instant. One moment fast. The next moment the sail is luffing and you're stopped. Or. If you're not paying attention, the boat's turning the wrong way and the sails are on the wrong side of the boat.

As you build a feel for it, though, you raise the tiller to push off the wind or you ease the main sheet. Or a little of both. You're balancing the two controls.

This is not a thing you learn in an afternoon. Indeed, I think this is a thing you acquire by feel when someone else is driving. You try to emulate the feeling when you are driving. I know I'd learned a lot from the summer I raced. I was crew — my job was to trim the jib and hike out, raise the spinnaker and move aft, and drop the spinnaker. The perfect balance between tiller and mainsheet was a thing I felt from the way my racing buddy drove the boat. By the end of the summer, I'd learned what well-handled felt like.

I think CA might have learned it from me.

That afternoon, CA drove the boat hard and well. She took us further down the lake than we'd ever been before. She found the point of balance where the sail power was in perfect opposition to keel and helm.

Consequently, CA drives under sail. I pull ropey things. The complexity of a ketch rig means CA tells me when the boat's being pushed up or pushed down by the wind. Often, it's a sail trim mistake I can recognize and fix. (I tend to overtire the main and mizzen.) Sometimes, we have to talk it through, because it can be tricky to figure out how to balance the rig.

Balance

CA is safety officer, giving the final word on any plans. This also means CA checks all the below-the-water-line apparatus. Mostly this means hose-clamps. CA has the official hose-clamp nut-driver and my job is to replace the clamps found to be loose or rusty or sketchy in some way.

I do engine and most systems work. Who really wants to change the oil? Same for the water filter. It's awkward and requires brute strength. I can take orders as well as anyone.

CA does the anchoring and mooring. I'm not as careful about feet and fingers.

I try to avoid operating things too many times on my own. CA can flip circuit breakers and check for leaks as well as anyone. The inverter's a right pain in the ass, but, it's manageable. I don't need to be the only one who can turn on the 110V AC systems. Indeed, it's bad if I am the only one.

One steep learning curve is the new chart plotter. It has a lot of options. CA has a preferred panel that shows the chart and the wind instruments. It's important to play with the controls to see what it can do, and how to get it back to displaying something useful. I can suggest, but CA knows that night watches require self-sufficiency with all the helm equipment.

The next big thing to learn is the new autopilot. It has five steering modes, of which two seem useful. The old autopilot steered a compass course. We need to spend time with the new one it until we're comfortable with how it works and how to control it. CA's impetus is to avoid the potential complexities of the fancy software and focus on the key issue of taking action to avoid hazards.