Suggestion:
In the next month or so, buy a
trailer sailer, and teach yourselves to sail. Do not try and jump start the
project with expensive charters. You'll want that
money to put towards a well found boat for your sail to
England. If you have a driveway, you may be able to store the
trailer sailer right there in your driveway, thus eliminating costs associated with berthing. Sail every sailable weekend for about a year, and then decide exactly what you want to do next.
Sometimes people don't care for sailing. Sometimes people can't find a cure for mal de mer, although most people are usually okay after 3 long, long days at sea. Anyhow, after that if all went well, start looking at more boats. Best is to find the smallest you think you can live with. People cross oceans in very small boats, people with small pocketbooks, or just loves "small" and "cosy". Read the old
Pardey books. May be hard for someone from
Texas, but boats are very much expressions of their owners, and so, for instance, you might find the 32-36 ft. range would
work for you for a cruising boat. It's easy to get seduced into thinking you need all the "mod cons", but every last one of them adds complexity, and therefore to hours of
maintenance. If you are KISS kinds of folks, the simpler you do it, the more freedom for exploration you'll have.
One other thing, join a local sailing club and volunteer to be "green" crew. Sail with as many different skippers as you can. This is better than lessons, the skippers bring you along, and while you start making up lines and packing chutes, eventually you'll be allowed other jobs. You'll also experience different styles of skippering, and that will be a guide for you. You'll see a variety of boats, and boat layouts, and that will inform your choice of what the cruising boat will actually be.
If you do eventually do lessons, do them separately from your significant other. It will not cost significantly more, but then you'll both have inputs from different instructors, and that is an extra bonus.
Ann