Top Ten Off-the-Rails Adventure

Sailing in Chicago, Illinois

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.

Quick FAQs

Rail Info ( 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.

Activity Info

Outfitter - Chicago Sailing Club: (773) 871-SAIL;

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


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