Published in text and recorded as a podcast for the now-defunct Keyscast, 2006

When most people think about bicycling in the Florida Keys, they think of long, quiet trails along the water, of back-country rides out on Big Pine, and of what I think of as the “Because It’s There” rides – the ones that go from a given mile marker to one of its absurdly distant cousins.  But the best ride in the Keys, I think, is on about as urban a trail as you can find down here.  It’s the lap around Key West.  Our ride features wildlife, scenery, challenging obstacles, and a nice snack.  Here’s how it’s done:

A couple hours before sunset, pull your car into the parking lot where Publix is, on North Roosevelt Boulevard.  Take the bikes down off the rack and head out of the parking lot, towards the water.  Cross Roosevelt and hang a left.   The water will be just on your right.  Don’t get distracted looking for manatees.  The sidewalk’s a little rough, so pay attention.  Roll past the Home Depot, and over the bridge, and past a little bit of a commercial area, and you’ll find yourself riding along more water, right by the City Marina.  Slow down a bit, even stop if you like, and check out the houseboats.  Take a moment to indulge the envy you’re no doubt feeling, and then continue on.  Hang a right at Palm, before you cross, and head for the Historic Seaport.  There’s a steep-grade bridge here, so get ready to shift, and pay attention as you crest it.  It’s not a wide sidewalk.  Stop at the top of the bridge to look around, especially back at the houseboats.  Then let the hill do the work, and get moving again.  You’re coming up on a little bit of a bike path, which’ll last ‘til you reach White Street, near Cole’s Peace, Strunk Hardware, and the Restaurant Store.

Ride a little farther, in the street now, and hook a right on Grinnell.  This’ll take you into the Historic Seaport, where you can stop, lock your bikes, and partake of one of the many raw bars in the vicinity.  (I’m partial to Monty’s.)  Save the margaritas for later, of course – the part of the trip requiring maneuvering skills and focused attention is coming shortly – but a dozen oysters or a couple of stone crab claws will fortify you for the rest of the trip.

Refreshed, walk your bike toward the harbor until you find the boardwalk.  Hang a left, and walk your bike the length of the boardwalk; past Turtle Kraals, past Schooner Wharf, past that little white building everybody pretends not to stare at.  Turn right, and walk past Conch Republic, past A&B, past the sunbathing girls on the big sailboats.  (It’s okay to slow down.)  You’ll come out of this on Front Street, where you may resume riding.   Mount up.  (Speaking of which, you’re about to pass Fairvilla Adult Emporium.  Riders with little eyes alongside should be prepared to distract those eyes or face questions.  Riders without little eyes along are free to stop and browse.)  Either way, your next turn is a left onto Key West’s main drag, Duval Street.

There are two options at this point in the ride: Get off and walk your bike, so that you might sightsee and people-watch more safely, or ride in the street, and see what you can while enjoying the challenge of dodging wandering visitors, impatient locals, delivery trucks, and better-left-unidentified puddles.  Whichever you choose, you are going to travel south past such storied storefronts as Sloppy Joe’s, the Garden of Eden, the La Concha (run up to the top if it’s a nice day), and Fast Buck Freddie’s.  Past the drag bars, past the pizza places, past restaurants of every level, past the rebuilding Croissants de France, past the Butterfly Conservatory, and finally to the intersection of Duval and South streets.

Detour briefly with a right turn, and pedal one block to South and Whitehead, where you will find the Southernmost Point itself.  It’s a thrill, but a short one, leaving you plenty of time to ride the block back to Duval, turn right, dismount, and walk out on the little pier.  There’s a nice view there: The sunset and the ship channel on one side, diving pelicans and a nice beach on the other.  It’s a good spot for a break.

When you’re ready – and you want to do this while it’s still light – ride back to Duval and South, and turn right onto South, away from the Southernmost Point.  There are a variety of ways to arrive at your next checkpoint, but, as you aren’t going to want to ride your bike while reading a detailed newspaper article, I’m just going to tell you to ride on South until you can turn right on Reynolds.  Turn right on Reynolds, and follow it south to Atlantic.

Now you’re on the beach, riding along with the water and sand on your right.  Ride out on the White Street Pier, if you like, especially at sunset.  Just don’t hang out there until it gets dark, as this next part of the ride isn’t anything special if you can’t see.  Keep rolling on the path along the ocean, past the beach vendors, past the condos, past the airport.  There are benches here and there along the way, so please feel free to stop and have a little sit.  Very relaxing, this ocean view.  (By the way, you’re technically on State Route A1A, which I know provides a mild thrill for some Parrothead riders.)  You’ll curve left up ahead, ride over a small bridge over a canal, pass the light at Flagler, and shortly come upon the only part of the ride where you probably ought to be paying a lot of attention, which is the point where the Overseas Highway meets Key West.  It’s not a big intersection, for those of you used to, say, Chicago, but it’s busy, and it’s complicated.  You have to pay attention, ’cause a lot of drivers coming through won’t.  Once you navigate it, though, you get to finish your ride with another nice run along the water.

If this seems like a lot of complicated choreography to ride a bicycle in a big circle around the outer edge of an island, well, that’s because it is.  So for those of you who prefer your ride-instructions simple, I offer this: Put the water on your right- or left-hand side, and keep that hand on the same side as the water until you come back to the place you started.

(But not stopping to enjoy the sights is a mistake.)