Communication
To attempt to answer your question, I went to my
highest authority: my wife, Marie, who had zero sailing experience 43 years ago, and now has over 100,000
blue water miles "under the keel". Here are her comments:
Does your wife swim? Does she love being on the water, or at the water's shore? Is she adventuresome?
Why is your
wife not enthusiast about a
boating retirement? You have to have this very
basic communication with your wife to be successful.
If the answer is "No" to these you are going to have an up hill battle and the chances for success are not necessarily good.
If the answer is "yes", Then your chances are far better.
We used to give lectures on both our adventures, and getting into boating/cruising--my wife's comments were more important than mine, despite my having much more experience. We followed many cruisers for years, and determined what worked, and what didn't.
Find
books to read and videos to watch for her--stressing the woman's role in sailing/cruising.
What are
her fears? Loss of her home, being out of touch with
children and friends? Discomforts? Pirates? Foreign travel? Meeting people? Being away from accustomed activities? Concern for parents? Phobias? Fear of something happening to the
skipper, and she left to handle the boat?
Our philosophy is that the partner (Admiral) has to become skilled in boat
maintenance, handling,
navigation, first aid, crisis management.
First step is both taking one of the
Power Squadron or Coast Guard Auxiliary courses. Do not be "overbearing", or "knowing" (For example, I took a basic course with my wife early in her sailing career. I didn't try and show that I knew anything about the material--and only gave suggestions when asked. Even then, I asked questions back, to lead her to her own conclusions--right or wrong.)
Make friends who people who have boats. This may come from the
boating classes, or from hanging out at--or joining a yacht club or organizations (such as sailing club, boat sharing club etc) Get your wife out on the water with a competent
skipper, who does not get upset or yell!. Get her out in the water.
As you both read
books about sailing, or watch videos, discuss them, and find out what are her concerns, based on that subject matter.
In our case, we first converted a 16 passenger commuter van/bus, into a small RV. This allowed Marie to have input as to what was important in a "magic carpet" we would travel in. It also introduced her to tools, and techniques:
wood working,
fiberglass, painting,
plumbing and
electrical (12 V DC and 110V AC),
flooring, bedding etc. With the knowledge that we were going to shortly transfer these skills to boat building. A year later we acquired a 38 foot sailboat
mold (Bankruptcy auction) with a lot of building materials. We laid down a 2 year plan,
both of us building this boat after our professional jobs, to complete this boat. We then took a 4 month sabbatical from our jobs to see how she liked the life. As it turned out, when we got as far North as Cape Mendocino, CA. from Long Beach, CA. she proclaimed: "
Buy me a pilot house boat, and take me where it is warmer---I will go anywhere warmer".
We found a good deal on an almost new 62'
LOA Ketch, and were able to buy it, with the
sale proceeds from our home, and the profit from the boat we had built. We had saved enough for at least years cruising, without touching any savings or
retirement funds. We worked side by side modifying and upgrading that vessel.
This path is not for everyone--and I had taught Marie how to sail, along the way in smaller boats, including getting her racing in Sabots, and
crewing in near shore and coastal races. However by the time we started our first 4 year voyage, she could handle all
maintenance chores and
repairs, plus had become a skilled sailor.
Go slow, be very aware of signs of discomfort--both physical and mental, in your partner. Stop, when you see these, and talk them over. Either cruising will strengthen your marriage, or it can destroy it. We followed over a dozen boats we had become very close to, who had survived the 1982 Cabo Storm and had goals of a long
cruise, as we did. Only 3 of us made our goals--sort of. One finished over 8 years later in a different boat--after they
lost the first one on a reef in the S. Pacific. The other also
lost her boat, but bought another, and continued to cruise--until an incident off
Baja years later spooked her out of continuing sailing. The other boats either got thru the
Panama canal and thus to the Gulf/Atlantic, and sailed to USA--selling the boats, and in a couple of cases a divorce, or selling the boats at some down
wind port in the S. Pacific.
You live in some of the best boating waters in the entire World. (We spent 4 years sailing out of Sequim and going up and down the Inside
Passage for 4 seasons--April the Oct.). It can be rough, foggy and cold, or its can be fantastic. Not always ideal sailing conditions, but pick the good days. Probably a club will be good at first. It does not have to be in cats.
You do need to take an excursion to a high profile boating market--such as S.
Florida where there are many cats
for sale, if that becomes your ideal boat. Buy that boat at the very least a year before the target leaving date is. Sail it, and made the modifications (water maker,
generator,
battery monitoring system, autopilots, modern
electronics etc). Figure out the amount you can afford for the boat--(I figure 25% over the
purchase price at least) Have a cruising
budget. Be sure your wife is fully involved in all of these processes.
Mal de Mar. I am a retired MD who worked with many long distance sailors for a long time. My suggestions are: eat lightly the day before sailing, sleep well, and take a Bonine (Meclizine HCL) at
bed time. Also first thing in the AM (be sure it does not make you too drowsy) No alcohol 24 hours before sailing. At the first time any motion sickness appears; a Bonine chewable under the tongue. I like to take the
helm, or be busy sailing the boat. Keep eyes fixed on horizon. Stay on
deck if possible. There are many stronger remedies, but this works for many folks. If not--send me a PM, and I will suggest more.
I also find that the motion of the vessel is instrumental in
sea sickness. For me it is a rapid snap roll. For others it is a slow roll. Fumes,
food smells, and other sick often make
sea sickness worse.
Good luck and pass your experience along to all of us, so we can also learn from your experiences; good or bad.
Except maybe Point 6—I never let my ego get in the way of my fear about damaging the 
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