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.

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
WHEN TO GO: April to October

Having earned her B.A. in journalism, Sharael is the climbing guide for and has been published in Working Woman magazine, Outside Online, and Wired News. She lives in the San Francisco Bay Area with her husband, where she enjoys mountain biking, kayaking, and rock climbing.

Published: 27 Nov 2002 | Last Updated: 14 Sep 2010
Details mentioned in this article were accurate at the time of publication


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