Yes, it’s burly cold right now in the Midwest. But once summer hits, Lake Michigan has 1,638 miles of shoreline, which is 600 miles more than California and 300 more than Florida. No wonder this Great Lake has become a fertile incubator for the SUP sensation's inland sweep. The lake borders four states and two of America's great cities, Milwaukee and Chicago. So from the city to the country, towering skyscrapers to vertical cliffs, Lake Michigan offers endless possibilities for SUPers who want to get on the water, get some exercise, take in the scenery and maybe even catch a few waves.
—Benjamin Marcus

Whether your taste runs to empty wilderness or urban bustle, touring options abound. In Chicago, launch from Montrose or Hollywood Beach and paddle five miles south to check out the city's skyline from just offshore. Head upstream on the Chicago River for a surreal trip through the city's Great Architectural Valley.
Similar adventures await in Milwaukee, which also boasts an eponymous river. Cruise along the coast or explore the Milwaukee Urban Water Trail, a 35-mile course along the Milwaukee, Menomonee and Kinnickinnic Rivers.

Crave a little more wildness in your adventure? Keep going north and you'll find yourself in places as untouched as California's Big Sur.
"Northern Lake Michigan is more wild and has a more varied coastline," says Ryan Gerard, owner of Third Coast Surf Shop in New Buffalo, Mich. "It's a great place to get away from everything." 

Surf conditions on all of the Great Lakes are fickle, inconsistent and seasonal. In a word: unreliable. But standup makes an inconsistent, windy, 2-foot day fun. In the summer of 2009, the city of Chicago opened the beaches at Montrose, 57th Street, Osterman and Rainbow to surfing. If city SUPing doesn't appeal to you, open Google Earth and follow any coast of Lake Michigan and you'll find miles of surf geography as promising as the north coast of New South Wales: long beaches, jetty breaks, point breaks and reef breaks. The wave-creating geography is there; all it takes is a good strong breeze to push some swell your way. Fall is the best time of year, and if there's no swell you can always enjoy the foliage. If you do score waves, don't forget to bring a camera. Otherwise, no one will believe your stories of how good it actually is.

After Hours
If all this paddling makes you hungry and thirsty, you're in the right place. Milwaukee is renowned for beer and sausage. Chicago is famous for beer, Chicago-style pizza, and the world famous Italian beef sandwich: thinly sliced beef slowly simmered in au jus, served on an Italian roll with sweet peppers or spicy giardiniera. And did we mention da beers? "The Livery in Benton Harbor, Michigan is a great regional brewery," says Gerard. "And there are two great paddling rivers there, too, the St. Joseph and Paw Paw." Standup rentals and guides are available at Kayak Chicago (