Sailing Hemingway titled his Parisian memoirs A Moveable Feast. The avid Caribbean sailor never chronicled his boating days, but here’s a title he might have used: An Unstable Picnic. A catamaran hardly qualifies as a sailboat; it’s essentially a trampoline stretched between two canoes with a mast. I do not recommend resting a cooler atop one, for Lake Michigan is less tranquil than it seems. A little gray sail house on the south end of Northwestern’s campus rents the three- or five-seat vessels to the public. Once you set sail, you can cruise about the less-populated waters and greener shores off the gorgeous lakefront campus—provided you reassure the incongruously tanned employees that you know what you’re doing by correctly answering some basic sailing questions. “It’s not a Bahamas resort,” the instructor says. “We won’t just give a boat to anyone.” So study up on jibs, close hauling and tacking before strolling up in Top-Siders (or pony up $339 for a four-week sailing class). Northwestern Sailing Center, 1823 Campus Dr, Evanston (847-491-4142). $45–$80 one hour, $65–$100 two hours.—Brent DiCrescenzo
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Hot-air ballooning Hot-air balloons are like the Love Boat of aviation, no? Lake Geneva Balloon Company offers a one-hour ride at sunrise or sunset at altitudes of up to 2,000 feet, plus a post-landing Champagne toast, for $240 per person. Pilot and owner John Trione explains that scheduled trips are often canceled five to six times before a successful ride, due to fickle Midwestern weather and breezes off the lake. You’re much more likely to have liftoff, he says, if you schedule a ride for the morning, when winds are calmer. Also note: You likely will be sharing this romantic ride with two strangers, so maybe not so much with the proposing—unless you schedule a private ride for $650 per couple. Lake Geneva, WI (262-206-3975).
Banana boating Straddling a giant banana may remind you of spring break in Cancun (in more ways than one), and in Chicago it looks just as ridiculous—and fun as hell. Recruit up to five friends to ride with you on the inflatable fruit that’s pulled by a Jet Ski as you hang on for dear life, jump waves and possibly get tossed during the 20-minute jaunt. North Avenue Beach, 1600 N Lake Shore Dr (jetskischicago.com). $20/person.
Kayaking If you’re keen on paddling around the lake or river in a sliver of a seafaring vessel, you have a lot of options. You can join a guided tour, from architectural to night paddle ($50–$70), sign up for lessons (around $85/class), or simply rent a kayak ($15–$30/hour for a single) and take off on your own. Outfitters include: Kayak Chicago, Wateriders, Chicago River Canoe and Kayak and Urban Kayaks.
Jet Skiing “Oh, my God, that just hurt my vagina!” screams the backseat rider on my rented Jet Ski after we fly off what feels like the millionth choppy wave we’ve hit on Lake Michigan. There’s no question we get an amazing view of the city zipping back and forth between North Avenue Beach and Diversey Harbor for our hour ride. But if you’ve never commanded a Jet Ski before, popping your cherry might be something worth saving for your best friend’s lake house: We get a few minutes of instruction before we hop on, but we never get over our fear of flying off or flipping the damn thing over. Plus, depending on how busy the waters are, you might find yourself in a game of Frogger with other nautical adventurists. But if you’ve got some cash to burn—riding solo isn’t cheap—and aren’t lucky enough to be friends with someone who owns a Jet Ski, this is your ticket to hitting the water. My advice: Grab a friend and pay the extra $10/rider fee so you can split the steep cost. North Avenue Beach (jetskischicago.com, 312-547-0543). $145/hour; $10/additional rider.—Mark Bieganski
Paddleboarding It’s similar to surfing except the board you stand on is wider and you’re using a paddle to move along the surface of the lake (okay, so it’s nothing like surfing). Spend the first 30 minutes of a small-group lesson learning how to stand up, stop and turn (skills that will come in handy when the Windy City lives up to its name). Luckily, the designated paddleboard zone will keep you at a distance from Castaways chaos and cocky motorboaters. Great Lakes Board Company at North Avenue Beach (773-575-4787). Group lesson $50/person; board rental $25/hour.
Paragliding Sure, there are a number of insane stunts you can pull in the sky, but paragliding is the only one that lets you do them while sitting down. Similar to hang gliding, paragliding has you catching thermals and updrafts, operating a large parachute to climb as high as the cloud base (roughly 6,000 feet), and travel distances as far as 100 miles. All, as Chicago Paragliding’s Jaro Krupa says, “while sitting in a kitchen chair.” 3234 N 700 East Rd, Chebanse, IL. Tandem launch $250.
Riding X-Flight If you’re like me, the idea of performing aerial stunts is exciting, but the life-threatening component dampens the thrill. That’s why the new X-Flight wing coaster at Six Flags Great America in Gurnee is a good alternative. Designed to simulate the feeling of dangling from an airplane wing, X-Flight suspends riders midair on either side of the track, so your arms and legs hang free as you barrel along at 55mph through tight turns, plunges and inversions. Just like hanging from an airplane but, thankfully, you’re not. 1 Great America Pkwy, Gurnee (847-249-4636). Park admission $40–$62.—Judy Sutton Taylor
Rappelling I’ve never rappelled before. Yet here I am, standing atop the 27-story Wit Hotel, ready to launch backward and walk down the building with the support of only a few ropes. Today’s event, the Skyline Plunge! Chicago, is for a terrific cause, with 100 participants raising nearly $130,000 for the Respiratory Health Association of Metropolitan Chicago. But that first step into, literally, thin air? Terrifying. I take a few more—foot to window pane, foot to window pane—and look around. I’m level with the giant Chicago Theatre sign. I can see down State Street for miles. And when my feet touch ground, raucous cheers from family and friends welcome me back to Earth. Can I go again, please? The next Plunge! is September 8 at the Wit Hotel (201 N State St). $150 registration, $1,000 fund-raising minimum.—Marissa Conrad