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Jump Onboard Chicago's Sailing Scene
Anchor-down for these sailing services that'll make you shout "ahoy!"
Tuesday Jul 10, 2007.     By Misty Tosh
Centerstage Chicago Nightlife City Guide Arts

If the choppy waters of Lake Michigan beg you to don a sailor's cap and shout "ahoy," then anchor-down and dig into our roundup of ways to get your sailing fix in the Windy City. The temp's not going down anytime soon, so you might as well get wet!

Take a class at 3rd Coast Cruising
Learn the ropes (or lines as they're called in the sailing world) at this relative newcomer on the sailing-lesson front, which offers a plethora of programs to fit every lifestyle. You can take basic sailing classes (nine hours for $290), private lessons ($100 per hour) or, for skippers who can't get enough time on the water, you can participate in unlimited summer sailing ($1,600 flat). A user-friendly, 30-foot sailboat serves as your classroom; classes on heavy-weather sailing, GPS and navigation are also available.

Rent a boat at Lakeshore Sail Charters
The time-honored process of sailing a boat is hard work; sometimes you just want to kick back, sip a frosty libation and watch the sun set over the backdrop of the city, while someone else performs the labor. Enter the extremely experienced owners of Crescendo, a slick 36-foot Beneteau ($140 per hour, two-hour minimum and six passengers maximum) and the Red Witch, a classic 77-foot schooner. This happy-to-oblige team will sail for you, leaving all the good times in your tropical-cocktail-heavy hands.

Watch the seafaring action at Montrose Harbor
This is one of the most accessible marinas in the city for spying on boats. Weekends can be hectic, though, when thousands of beach-seeking bunnies set up shop on every square-inch of green. Besides being the best place for viewing the so-close-you-could-touch-them sailboats slipping out of the harbor, this beachfront gem has it all: staggering city views, prime real estate for fishing by the lighthouse, Mexican street vendors hawking tacos and popsicles and hidden bike paths. Plan on getting there early, when free parking and the best lounging spots are still available.

Buy a share at SailTime
Let's say you ache to get your paws all over a brand-spanking-new sailboat, but you don’t have the funds to go top-notch. If so, fractional sailing is for you. It works like this: You buy a seasonal membership and get seven sails per month, anywhere around the world where they maintain a fleet of boats. In return, SailTime pays for insurance, slip fees and maintenance costs, as well as keeping the boat spic and span. Chicago's SailTime homebase is at Burnham Harbor (next to Soldier Field), and once you get ASA certified (which it can help coordinate) the boats you'll be cruising on are the beautiful (and expensive) Hunter 33s and 36s.

Scope a boat at Sailboat Sales Company
Located on the far south side of Chicago within the confines of Crawley's Yacht Yard, this tiny but knowledgeable company keeps a league of sailboats for sale for those of us who need to have one right this second. Even if you decide not to drop the dough, you can take your time getting up close and personal with boats you fancy and make notes for the future. Teak or fiberglass deck? Blue or red hull? Manageable 25-foot cruiser or mega 52-foot yacht? The options are endless, and the experienced staff will help you sort out your dreams; all at no cost to you.