You don't have to be Dennis Conner to experience the exhilaration of sailing, which is more visceral than a motor boat and more thrilling than a sea kayak. Small sailboats like the Hobie Cat or Laser are surprisingly nimble, yet not terribly difficult to master. (Large live-aboard yachts, on the other hand, require considerable training.) Once you get the hang of it, sailing is something you can dabble in every time you go to the beach—many resorts have Hobie Cats available to guests, and beachfront water sports centers rent them by the hour. Most hold two to four passengers, making for a fun family or couple's outing.

What it takes: Plan on taking at least five hours of lessons, depending on the conditions, the type of boat you're using, and the time it takes you to grasp the basic concepts. Lighter winds are best for learning—you'll be surprised at how quick a Hobie Cat can move with just a gentle breeze.

Who can do it: Sailing is a bit like being a puppet master. There are various ropes and pulleys to loosen and tighten, a metal bar for controlling the rudder, and you always have to mind the wind and boat direction. You don't have to be exceptionally athletic, but coordination and a mind for multitasking definitely help.

Where to go: A number of resorts in the Caribbean have formal sailing schools, and they are the best places to learn. Bitter End Yacht Club (www.beyc.com) in Virgin Gorda, British Virgin Islands, is a terrific family resort, with an emphasis on sailing but also offering diving, windsurfing, and other sports as well. The two-day Learn to Sail course includes six hours on the water and promises to have you solo-sailing a Rhodes 19 by graduation. More advanced courses are available, as well as kids- and women-only programs and fun Sunday regattas. Alternatively, many ordinary resorts have small sailboats for guests to use or rent. A trained guide always accompanies beginners, and most are happy to show you the ropes if you simply ask.

Tip: The beach at the Bitter End isn't terrific, but better ones are a short distance away—after completing your course, you can sail there.