Destination: Sandy Hook, New Jersey
Miles on the bike: 8 (not including nautical miles)
What to do when you get there: After a ride to Wall Street's Pier 11 and a beautiful (if slightly expensive $40 round trip) journey across New York harbor on the Seastreak ferry, you're in a federal park at the Jersey shore's northernmost tip. Don't miss the oldest lighthouse in the country, but also don't spend too long biking around Fort Hancock (built 1895) on the paved, well-kept trails; you're here for the seven public beaches—one of which is "clothing optional." You know what that means... (It means don't bother packing a bathing suit.)
Destination: City Island
Miles on the bike: 20
What to do when you get there: City Island is a New England beach town that New York City caught and never released, so one goes there to eat seafood and drink beer in the sun and, if one insists, go boating (preferably not in that order). For seafood, your best bets are Johnny's Famous Reef Restaurant (2 City Island Ave) and Lobster Box (34 City Island Ave), where the crab is superb. Walk off your bounty-of-the-sea binge on quaint streets lined with Victorian homes.
Destination: Astoria Park (across the Bronx Kill span of the Triboro)
Miles on the bike: 8 (go into Manhattan first, for the fun of it...)
What to do when you get there: Well, getting there is a big part of the fun... Coming from Manhattan, the Bronx Kill crossing leg of the Triboro is a ride up steep concrete Brutalist ramps, and then, on the Queens side, it involves carrying your bike up stairs, and then guiding it down along metal wheel ramps. Towards Astoria there's a small passage with a chain link fence only 4 1/2 feet tall and between the vibrations of the traffic and the gusty winds, you'll experience a great rush adding to the unhindered view of the water below... If you survive, beautiful Astoria Park—and its giant, must-dip Robert Moses pool—awaits. (And if you're hungry, wonderful Greek restaurant, Agnanti, faces the northeast corner of the park.)
Destination: Floyd Bennett Field
Miles on the bike: 12
What to do when you get there: Forget the actual sights at NYC's first but long-since decommissioned airport—the old runways and hangars—and explore on your own: disobey signage and evade the fuzz as you wriggle through fences to stumble upon bona fide urban ruin. Sleep at the city-limits' only campground! Pack a copy of Netherland, to marvel at Joseph O'Neill's descriptive power! ("If a troupe of Mongolian horsemen had appeared in the distance I would not have been shocked." Srsly!!)
Destination: Wave Hill
Miles on the bike: 19
What to do when you get there: Peep the art exhibits, enjoy the pergola-framed Hudson River vistas (gasp!), or delight in the many gardens, which give even the New York Botanical Garden across the borough a run for its money: hit up the wild species garden (gosh!), the flower garden (golly!), or just roam the 10-acre forest that wraps the grounds (wow!).