When it comes to sailing, there are all kinds of things to learn how to do. How you go about learning will depend on your particular style. For example, I am not patient enough to take classes, and have always relied more on the written word and on-the-water trial and error than on more formal modes of instruction. Here are examples of ways you can acquire the skills you feel you need:
Community colleges, marine chandleries, Coast Guard Auxiliary, boat shows, and a number of other enterprises offer seminars, workshops, and courses on a variety of topics related to cruising. If you learn best in a classroom or group environment, check out resources in your area.
Get one-on-one instruction.
Hire a sailing instructor. Look over the shoulder of a diesel mechanic. Talk to a sail maker. If you learn best through individual instruction and consultation, there should be any number of experts available that you can hire, exchange services with, or otherwise remunerate in return for instruction on a particular topic. Read everything you can get your hands on. Some people learn best through the written word. There are scads of books out there about every topic pertinent to cruising, so if you enjoy learning by reading, there is plenty of resource material available. Check out FineSailing.com for endless sources of information.
Learn on the water.
There are those who learn best by doing. Boat handling skills in particular are probably best mastered in situations. Which leads me to the next 'preparing to prepare' topic.
Getting Out on the Water
Find ways to get yourself and your partner onto the water, either separately or together. No matter how much you learn from books and courses, on-the-water experience is a great way to really solidify your skills. This will also help you decide if being on the water is worthy trying as a lifestyle.
Go with friends.
If you have friends with boats, go out with them. If you don't have a boat yourself, this will give you time on the water. If you do have a boat, this will expose you to different boat characteristics and equipment.
Charter a boat in your home waters.
If you are within easy reach of a body of water, charter a boat of the type or types that you are considering cruising. Vary the amount of time, the kind of boat, and the nature of the weather that you go out in. Charter a boat in faraway waters. Consider taking boating vacations in other parts of the world. Besides exposing you to different types of boats, this will put you into different environments and weather patterns.
Participate on a racing crew.
If you live in an area with an active racing community, either or both of you can join a crew (I question whether you and your spouse would want to be on the same crew, but that's up to you!).
Many coastal cities and town have 'Beer Can' races during the season that are a little bit more laid back and convivial than the mainstream racing events; these are best to participate in if you don't want to be a blood-n-guts racing competitor.