Go for It
Learn the basics at Steve & Doris Colgate's Offshore Sailing School. Their ten-day Fast Track to Cruising course in the British Virgin Islands will certify you to skipper your own 50-foot yacht, though you'll want to practice in the Caribbean's calm water before tackling the Atlantic. From $3,150; 800-221-4326, www.offshoresailing.com
FOR AN AMATEUR SAILOR, navigating the Atlantic Ocean is a huge achievement. When you don't see land and just a few ships for days, there is a great sense of freedom and adventure out there on the sea. If your aim is to maximize pleasure, set off in a bareboat setup with a four-person crew, minimum. The three-to-four-week crossing is a challenge, for sure, but it's also very possible to do if you prepare both your skills and your equipment properly.
SKILLS & TIPS: First, solidify your sailing skills in a dinghy, a small boat that's usually shorter than 15 feet long. Being in a small craft forces you to learn how to balance a boat, as well as get a sixth sense for the wind and how it affects the craft. Once you're proficient, look for your oceangoing vessel, something around 40 feet long; this will provide a relatively sturdy, safe, and comfortable ride. Regardless of length, you want a monohulled boat, not a multihull. If you get knocked down in a squall in a multihull, you can't right it, and your trip is over.
When organizing your boat, make sure to have a replacement for every part—with the possible exception of the mainsail. Then take apart every piece of equipment you can and learn how to reassemble it; you'll inevitably have to fix something at sea.
Usually, the best time to set sail from the U.S. is from mid-June through the end of July. You'll avoid the stormy winter; iceberg season, which runs from April through the beginning of June; and hurricane season, from the end of August to September. If you're sailing from Europe, go anytime from November through April, as you'll travel with the trade winds that bring you south to the Caribbean Sea.
Avoid sailing too close to a storm because you're greedy for speed. Not only is it dangerous; you risk running into a headwind, which will force you off course. The other mistake is the opposite: being paranoid of the gales and sailing into a windless high-pressure area. You'll have to use your motor often, and you may run out of fuel—and a no-wind/no-fuel combo is worse than facing the gales. Stay on the northern edge of the Bermuda high, a subtropical high-pressure system in the North Atlantic, and it will carry you along in good style.
TRAINING: You don't need to be in killer physical shape to sail across the ocean; if you can easily move and raise the sails, you'll be fine. But practice climbing the mast while the boat is tied to the dock. Going up and having a look around at sea is one of sailing's hardest tasks. Being familiar with it will be an advantage.
—As told to Dimity McDowell