Step1
Get a boat. Even a small one will let you practice sailing and boat-maintenance skills.
Step2
Make sure you and your family know what to expect from life aboard a boat. No matter how large your vessel, storage, space and fresh water are limited, and refrigeration is limited or nonexistent. Take a test cruise by chartering a boat for a week or two.
Step3
Take short overnight trips on the boat and gradually increase your exposure to the open ocean. Evaluate your skills and equipment, then prioritize what needs improving. Ask cruising veterans for advice. Most coastal marinas have a few captains with considerable ocean experience who are happy to share their knowledge.
Step4
Practice boat repair. The boatyard can handle repairs at home, but out at sea, you're the boatyard. Wise skippers know basic repairs for standing rigging, running rigging, the engine, throughhull fittings, Fiberglas, electrical and plumbing systems, and so on.
Step5
Become competent using ocean safety gear until you become expert--very high frequency (VHF) radio, radar, weather reports, charts, global positioning systems (GPS), life rafts, storm sails, sea anchors, Watermakers (reverse-osmosis desalination system, found at Watermakers.com) and harnesses. Then decide which of these items is essential--a topic of considerable debate among experienced boat owners.
Step6
Evaluate your boat. Is it large enough and suitable for extended ocean cruising? Will your new gear plus food, water, fuel and spare parts fit comfortably and safely? Most people are happiest with a cruising boat of 37 feet (11.3 meters) or more, but many sailors cruise in smaller boats. Construction quality and seaworthiness should take precedence over size.
Step7
Pore over charts. The Caribbean is a logical choice for sailors on the Atlantic; Mexico appeals to Pacific sailors. Both have balmy weather, warm water and plentiful harbors.
Step8
Set a realistic budget based on your preferred lifestyle. If you always anchor in remote spots and avoid flashy towns, you can cruise very cheaply. If you'd rather dock in marinas, occasionally sleep in hotels and eat in restaurants, budget several hundred dollars per day. See 226 Set Up a Budget.
Step9
Keep your boat in good shape and shop around for insurance. The Boat Owners Association of the United States (boatus.com) offers marine insurance to members.