It goes without saying that the Windy City is the perfect place to try your hand at sailing. Perched on the perimeter of Lake Michigan's 1,660-mile-long shoreline, Chicago brims with opportunities for water-borne escape, meaning you need not stray too far from the urban buzz to enjoy some natural, wind-powered adventure. Budding mariners should enroll in an introductory sailing course to get to grips with everything from sailing terminology and wind direction to trimming the sails, man overboard drills, and tacking techniques. For the more adept, why not rent your own vessel and take your friends for a cruise in the shadow of the soaring Sears Tower? A romantic (or flashy) alternative might be to commandeer your very own private skipper as part of a yacht charter.
(www.amtrak.com/holiday.html for full details)
ROUTE: San Antonio, TX to Chicago, IL
LINE: Texas Eagle
DURATION: 31 hours (leaves San Antonio daily at 9 a.m.)
PRICE: $246 to $460
SCENERY: Desert, bluffs
ARRIVAL TRANSPORTATION: Redline underground train to Addison Avenue. Walk six blocks east to Belmont Harbor, or take a cab for about $10.
OUTFITTER: Chicago Sailing Club: (773) 871-SAIL; www.chicagosailingclub.com
WHAT TO BRING: Sun protection, sweater, long pants, water-resistant windbreaker, light-colored, soft-soled shoes, camera
DURATION: For the "Basic Sailing 101" course, five weekday classes for three hours each, or four weekend classes lasting four hours apiece
PRICE: $395 to $430
DIFFICULTY RATING: Easy
WHEN TO GO: April to October
Details mentioned in this article were accurate at the time of publication