New York's boroughs, demystified
It's not easy to choose between Bike the Big Apple's six standard five-to-seven hour tours; they all take in a great range of neighborhoods often skipped by typical tourist routes. Our favorites might be the Bike and Bite Brooklyn options, one of which weaves through Manhattan's Lower East Side, across the Williamsburg Bridge into Brooklyn, and through the hipster and Hasidic Jewish sections of Williamsburg—stopping at a local brewery and a gourmet chocolate shop—before returning to Manhattan via the Brooklyn Bridge. Bike the Big Apple, 877/865-0078, toursbybike.com, from $65 with bike, helmet, and two guides; kids 8 and older pay the same price.
Chicago north and south
Bike and Roll Chicago's daily three-hour tours wind through the Windy City's residential streets, alternating between routes in the city's North and South sides. The first itinerary takes you north to the mansions of the Gold Coast, through Old Town, along the tree-lined lanes of Lincoln Park, and past Wrigley Field in Lakeview. The second route ventures south to the Mies van der Rohe-designed Illinois Institute of Technology, around the Prairie District, past Clarke House (the city's oldest house), and into Chinatown. Bike and Roll Chicago, 888/245-3929, bikechicago.com, from $30, students from $25, with bike, helmet, and guide; these tours are not recommended for children younger than 13-years-old.
In addition to daily tours of Capitol Hill and the national monuments, Bike the Sites offers a tour through D.C.'s leafy, residential northwest quadrant that is inspired by the picture book Wild Washington Animal Sculptures A to Z. Beginning with a walking tour of the National Zoo, the Wild Washington itinerary continues by bike along Rock Creek Park and the National Mall, while a guide explains all the animal references found in the monuments and fountains along the way. Bike the Sites, 202/842-2453, bikethesites.com, $40, with bike, helmet, snack, water, and guide; these tours are not suggested for children younger than 13.
Around the bay
Views of San Francisco from the Golden Gate Bridge are already impossibly picturesque, but at the pace of a bike, they might be even more so. Depending on your pedaling speed—and whether you want to take a ferry back from the quaint towns of Sausalito or Tiburon—the route from Blazing Saddles' Fisherman's Wharf location, across the bay and back again, can take as little as three hours. Unlike the above tours, this one is self-guided. Blazing Saddles, 415/202-8888, blazingsaddlessanfrancisco.com, day rental $28, kids $20, with helmet and map; ferry from $7.
Related Story Rolling by the River: Bike Tours of New Orleans