Tried-and-true ways to transform a sailing into your best vacation ever

Step 1: Select the right ship
When Jean-Paul Sartre wrote, "Hell is other people," he must have been trapped on the wrong cruise ship. The single most important thing you can do to ensure an enjoyable time is to sail with like-minded travelers. To help you land in the right crowd, I've outlined the type of passenger you're likely to find on different cruise lines. The second most important consideration is size, the third is features.

How much does size matter?
The number of passengers is a ship's most vital statistic. Is your main goal to sightsee in small, picturesque ports? Then you need a small vessel (500 passengers or fewer). Or are you looking for fun and games in a floating amusement park? Then you need a vessel large enough to provide the necessary facilities and entertainment.

Will the ship's features suit my interests?
Say you're a foodie. You'd probably like a ship with a restaurant attached to a celebrity chef (the Crystal Serenity has a Nobu Matsuhisa restaurant, the Queen Mary 2 has a Todd English eatery, and Charlie Palmer oversees the menus for Seabourn's three ships) or a line that brings guest chefs on board to give cooking classes (as Silversea and Holland America do). Think about what you will require to be happy: A well-equipped fitness center? Substantive child-care programs? A choice of casual restaurants? A giant casino?

Step 2: Choose the right itinerary
You probably already know what region of the world you want to sail in. Now you need to choose among the itineraries offered there by the cruise lines that best suit you.

Which itinerary will give me the most bang for my buck?
If only it were as simple as looking at the list of ports included in each voyage and then choosing the sailing with the greatest number of places you've always longed to see. Since that's what most consumers do, cruise lines market itineraries packed with big-name ports. What many travelers don't realize until it's too late is just how limited their time is in these towns and how unpleasant the ports are when overcrowded with passengers. The larger the ship, the more time-consuming the process of getting off and on again, especially if the ship is anchored—which means everyone must be ferried to shore by tender—rather than docked. Additionally, if you've been to St. Thomas when the cruise ships are there, you know how an extra 25,000 people on an island can ruin the experience. While large ships tend to call at busy, built-up ports—since these have the infrastructure to handle an extra 25,000 people—small ships tend to call at more unusual places. My Caribbean cruises on Windstar, for instance, have introduced me to jewels such as Bequia, Île des Saintes, and Jost Van Dyke.

So how do I evaluate an itinerary?
The main factors to consider are:
How long is the ship in each port? Larger vessels tend to leave at 5 or 6 p.m., probably to increase their revenues, since passengers then spend money on board—in the bars, casino, gift shop—rather than onshore (when a ship is in port, all its revenue-producing outlets must close). Smaller ships spend occasional evenings in port, which is great because you needn't race back to the ship and can do those things that can only be done at night. To understand how much every hour in port counts, see "How to Read an Itinerary," right. On a Crystal cruise that I took in the Mediterranean, for instance, the ship remained in Cannes all evening, which allowed me to go to Monte Carlo and look for a tuxedoed James Bond in the historic casino.