By Bob Payne

Christopher Columbus had to slog across an ocean with a boatload of people who smelled like wet shoe leather before he got to the best part of sailing: cruising among islands or along an unfamiliar shore. Today, though, name any body of water, anywhere in the world, and somebody probably offers sailing vacations there.

Chartered Boats
Charter boats typically range in size from 30 to 50 feet and cost $1,500 to $5,000 per week. Unless you’re into a nautical version of Animal House, never sail with more than a party of six, no matter how big the boat. If you are overly concerned about sea sickness, charter a catamaran (or take up golf).

Most popular chartering areas are outside of the United States, so another consideration is travel time and cost. The South Pacific and the Seychelles can run $1,500 or more for airfare, and you need a two-week block of time for just one week of sailing. On the other hand, flower-bedecked, ukulele-strumming locals seldom float past your porthole on the Chesapeake. But different areas require different levels of ability.

Bareboat
If you want to charter a bareboat, on which you’ll serve as your own captain, the first step is to see how your skills match up.

Requiring the least experience are the British Virgin Islands, where the winds are usually gentle, the seas calm, and the navigation is by eyeball. New Zealand's Bay of Islands is easy, too, but you must be comfortable with the occasional blast of air. In the Grenadines, French Polynesia, and the Seychelles, you'll need to be proficient at making short (a few hours) open-ocean passages in occasionally boisterous winds. You'll need specialized skills in the Florida Keys and the Bahamas, where you often navigate in coral, or Chesapeake Bay, where knowing how to separate yourself from the bottom is requisite for exploring backwater creeks. Heavy-air experience helps in Greece, where sudden summer winds, called meltemi, can blow the fillings out of your teeth.

Crewed Boats
If you don't have the skills, consider a crewed charter. The "crew" can range from a captain only ($100-$150 per day), who might be there just to oversee things as you handle most of the sailing, to a full complement (usually found only on larger boats, costing $6,000 or more a week), who only require you to choose your entrees for dinner. In some locations, another option is flotilla sailing. You sail your own boat, but in the company of other boats, all being watched over by the flotilla organizer.

Bob Payne has sailed most of the way around the world. He has been a contributing editor of Sail magazine for 20 years, a contributing editor for Condé Nast Traveler, and a frequent contributor to Outside. Twice a month Bob treats iExplore readers to insights and advice from his latest journeys in his column "i on Adventure."