When preparing to cruise for the first time, I spent a lot of time researching...as do most people embarking on the lifestyle. I was looking for the answers that would ensure that I got it right.

Here are some of the common questions asked in seminars, at yacht club bars, and on the marina docks, along with what I’ve come to believe are the “right” answers.

What is the ideal cruising boat?

The boat I cruise aboard today is 30 feet, and I recommend one either larger or smaller, unless you fall in love with a 30-footer that wants to take you to sea. Most people seem to be comfortable in the size boat that they can afford. As far as building materials, I’ve known cruisers who are sailing in wood, steel, fiberglass, aluminum, and concrete. And get a sail boat, unless you prefer a power boat.

How much preparation do we need to do before we take off?

No doubt about it, preparation needs to be done. Being completely prepared, though, is like being perfect—it is an elusive condition. There is always something. Some people keep preparing and preparing and never go, while others take off the day after they take ownership of the boat. Prepare, by all means. At the same time, recognize that cruising has a large on-the-job training component, and don’t use preparation as a reason not to untie the dock lines.

What supplies should we take with us?

Like preparation, this could turn into an endless list. Take something, and understand that no matter what you take, you’ll wish you’d taken something else.

How do I know the best way to anchor?

Anchoring varies with conditions, so what worked today may not work again, even in the same anchorage. The real test is that you know, after you’ve dragged anchor, that something is wrong.

Should we take others with us?

Good idea. People share the work and expense. And bad idea. They cause extra work and expense.

How much money will it cost to cruise?

We’ve learned that it’s a good idea to have a budget before leaving, because then we get a good idea of how much is not enough. Financial demands are gaseous in nature—they expand to fill their container. Cruise with or without money, if that’s what you want to do.

When is the best time of year to go?

There is good weather and bad weather everywhere all year long. You should always attempt to get the right kind, and remember that is not always going to happen.

The point, in case I didn’t demonstrate it clearly, is that there are no “right” answers.

Cruising is Zen in nature: Full of paradox and oxymoron. If you can hold two opposing ideas in your head at the same time, stay with it. You are heading in the right direction.

Oh, and remember that there’s always luck—and that there are two kinds!