Seventy-one percent of the planet is underwater, so expand your global playground by learning to sail. Schools nationwide can teach you how to read the wind, handle a boat, and eventually skipper your own chartered bareboat. Just make sure the schools are certified by either U.S. Sailing (800-877-2451, www.ussailing.org) or the American Sailing Association (310-822-7171, www.asa.com). If you've never rigged a mainsail, you'll need to take three courses—keelboat, cruising, and bareboat—for a bareboat-charter certification. Each class takes three to four days, and while a keen sailor could package them together in a week, it's best to spread them out over a couple of seasons.

J World Sailing School
Newport, Rhode Island
If your idea of sailing includes sipping champagne on a yacht with Paris Hilton, don't enroll in J World Sailing School: It's for students dedicated to mastering the sport. Ranked by Practical Sailor as the country's top sailing school, J World offers six hours of on-the-water instruction every day. The three courses (including a five-day live-aboard cruise) start at $2,645. 800-343-2255, www.jworldschool.com

Boston Sailing Center
Boston, Massachusetts
With an average wind speed of nearly 12 and a half miles per hour, Boston is blustery. Couple that with a historic harbor known for heavy boat traffic, myriad shoals, and more than 30 islands and it's no surprise that Boston Sailing Center teaches technical sailing at its dead-reckoning best. The 30-year-old school offers a Macro Cruising package, combining all three courses students need for a bareboat-charter certification, for $2,050. 617-227-4198, www.bostonsailingcenter.com

Fairwind Sail Charters
Chicago, Illinois
There's no better way to see the Windy City skyline than under full sail on Lake Michigan. Chicago's Fairwind Sail Charters has a fleet of five boats up to 37 feet long—similar in size to what you might skipper on a Caribbean flotilla. Even cooler, the school sits near Shedd Aquarium and the Field Museum, just in case you feel the need for some culture while getting your land legs. Fairwind's three-course combo costs $1,200. 708-442-2670, www.fairwindsail.com

Harbor Sailboats
San Diego, California
San Diego has an average annual temperature of 64 degrees, a large sheltered bay that flows into the Pacific, and a community steeped in nautical tradition. What better place to learn the difference between a boom vang and a spreader? Harbor Sailboats' 40-boat fleet offers live-aboard instruction off Santa Catalina Island. Or head south for schooling in Ensenada, Mexico. The three-course bareboat certification starts at $1,150; customized seven-day live-aboard bareboat certifications start at $3,500. 800-854-6625, www.harborsailboats.com

Offshore Sailing School
Fort Myers, Florida
When Steve Colgate was 19, he raced from Cuba to Spain. Fifty-one years and more than 100,000 sailing-school graduates later, the former Olympic sailor and his wife, Doris, have become two of the country's top sailing educators. Though headquartered in Florida, Offshore Sailing School offers courses from Lake George, New York, to Tortola, British Virgin Islands. They also offer classes at the 330-acre, $140 million, full-service South Seas Island Resort, on Florida's Captiva Island. Offshore offers all three certifications from $1,990. 800-221-4326, www.offshore-sailing.com

Windworks Sailing Center
Seattle, Washington
Sure, it rains a lot in Seattle. But in a strong downpour you'll hardly notice the sea spray hitting your face as you cut through Puget Sound on a 37-foot Bavaria. Windworks Sailing Center can get you bareboat-certified from $1,686, which also includes a coastal-navigation course. A five-day live-aboard to the San Juans with the full course load starts at around $5,000 for three people. 206-784-9386, www.windworkssailing.com

Flotillas
Think of a flotilla as a nautical caravan, a fleet of yachts hopping through exotic archipelagoes in search of stiff wind, safe harbor, and a big bowl of rum punch. Whether you want to learn skills by crewing under an experienced captain or skipper your own boat, flotillas are for sailors of all abilities.

The Grenadines
Add a splash of grenadine to your screwdriver and you've got a vodka sunrise; add a week of the Grenadines to your sailing vacation and you've got a Moorings flotilla. In July, August, and October, the charter company offers eight days of sailing through this southern Caribbean chain, with prices starting at $1,930, meals not included. 800-535-7289, www.moorings.com

Thailand
In 2005, Sunsail set a course around the islands of Koh Samui, Koh Phangan, and Koh Tao with its first Gulf of Thailand flotilla. This May, complement seven days of island hopping, including a two-night anchor in Ang Thong Marine Park, with a week of racing in the Koh Samui International Regatta. From $4,500, meals not included. 800-327-2276, www.sunsail.com

Norway
Sail in the grand Norwegian nautical tradition of the Vikings with NorseAdventure Yacht Charter's two-week Norwegian flotilla. Hop aboard a 47-foot Beneteau between June and August and you'll explore castles and fjords. From $5,592. 011-47-913-91-439, www.norseadventure.com