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Day 57 Key Largo to Key West, 4:54, first sub 5 hour century in 8 years

Like Jimmy Buffet said when he closed out his summer tour at Fenway Park, "I can think of no better way to finish a journey."



I even managed to out run the rain to finish my 3,000+ mile journey. I was only supposed to ride 41 miles today but my legs were feeling strong so I rode all the way from Key Largo to Key West in one shot. The rest of my group will arrive tomorrow.


I started riding on the bike path but got tired of dodging puddles, cracks, and curbs which limited my speed to 16mph. The bike path also frequently switched from one side of the Overseas Highway to the other side and then back again, each time requiring a left turn across multiple lanes of highway traffic. Instead, at mile 10, I simply rode along the shoulder of the Overseas Highway all the way to Key West. Had I simply done so from the start I probably could have shaved another 10 minutes of my century ride time. The shoulder was present the entire way save for a 5 mile stretch in Marathon where I simply took the entire right lane. A few yahoo’s in lifted pickup trucks barked at me but the lane was clearly marked with a sharrow. Additionally, there was a 3 mile stretch coming into Big Pine where the shoulder was only 2 foot wide and so pitted that your teeth rattled, but it still looked better than the sand covered bike path.


I made a few brief photo stops along the route, most notably at the Hurricane Monument in Ismalrada which was carved from local coral stone on November 14, 1937 to commemorate the 408 lives lost during the Category 5 hurricane that struck on Labor Day, 1935. At the time the only means of transportation on or off the island was by train and the rescue train was knocked off the tracks by a storm surge. The monument has a simple brass plaque with the following inscription.

“This memorial is in memory of the war veterans and the civilians whose lives were tragically lost in the hurricane of September, second 1935.”


I also grabbed a shot of the largest osprey nest I have ever seen, I guess there’s plenty of fish in the local waters.


Enroute from Key Largo to Key West you transit an astonishing 44 islands and 42 bridges. Here are some views from several of the bridges including the famed 7 mile bridge with Pidgin Key and the abandoned railway bridge in the distance.





In Big Pine I considered a 6 mile detour to see the Blue Hole which I was kind of ambivalent about. It is an abandoned mine with the only fresh water, and the only alligators, in the Keys. I have seen plenty of alligators in my many trips to Florida and the weather was taking a turn for the worse. I had just received a text, from my buddies 30 miles behind me, that it was raining in Marathon and heading my way. One look at the sky behind me convinced me to ditch the alligators and soldiered on towards Key West.

I had a 6PM dinner reservation but at 5 I was already famished so I ran over to the Ocean Grill & Bar, 1075 Duval St for a sumptuous feast starting with an avocado salad and finishing with a perfectly cooked Argentinian steak. I passed on dessert as I had other plans.



After my early dinner, I took a leisurely stroll down Duval Street on my way to Mallory Square to catch the famed Key West sunset. During the day and early evening, Duval is a sleepy street where the chickens sometimes outnumber the tourists. In many ways it reminds me of Siint Maarteen, the Dutch side of the island, where chickens roam freely through town. As the sun goes down Duval Street comes to life. The pubs begin to fill but the bulk of the crowd moves like the tide to the largest party in town, the Sunset Pier at Mallory Square. Needless to say, I was carried away in that current.












It was overcast and rain was threatening but a cast of nearly a thousand was already assembled on Mallory Square as well as the decks of the adjoining restaurant, pubs, and hotels. The water was teeming with sunset cruise ships overflowing with inebriated guests. Everyone had come with one goal in mind, to drink, dance, and watch the orange glow from the sunset. There really isn’t much else to do in the evening on Key West, unless you want to wager on turtle races at Turtle Kraals.





I’m not much of a drinker so I just sipped club soda and danced to the Jimmy Buffet style music from the main stage on the Sunset Pier. Just as the sun was about to drop below the horizon the lead singer put in a futile plea for the mega yacht blocking much of the horizon to “get the f**k out of our view.” They immediately broke into Kenny Chesney’s song, “When the sun goes down.”

Cause when the sun goes down, we'll be groovin

When the sun goes down, we'll be feelin all right

When the sun sinks down over the water

Everything gets hotter when the sun goes down



When the sun finally set, a orange fireball lit up the horizon dwarfing the mega yacht. It’s too bad that I didn’t have my real camera with me to capture the visage better. The shadow of the yacht did nothing to dampen the blood curdling screams from the masses assembled onshore and on the sea.


The vibe was real good, I only wish Molly could have been here to enjoy it with me, so I hung out till way past dark. On the way back to my hotel I made a stop at Kermit’s Original Key West Key Lime Shoppe, 200 Elizabeth St, for what I was told would be the best key lime pie I had ever had. Kermit’s did not disappoint.



The walk back down Duval Street was surreal. The locals actually have a name for it, The Duval Crawl. Key West's World Famous Duval Street stretches from the Gulf of Mexico to the Atlantic Ocean. In between there are currently forty three bars that must be visited to complete the infamous Duval Crawl. It appears that many folks were attempting just that. There were bars of all sizes, including one barely large enough for a single person to step inside. The pubs were so full that patrons were overflowing onto the street, with to go cups in hand. I frequently needed to walk on the street as there was no room on the sidewalk. In addition to booze, the pubs were hawking girls, drag queens, and music to draw additional customers. Music was everywhere and many hopeful musicians were roaming the streets with guitars slung over their shoulders like weapons. I stopped to listen to the ground floor musicians, many more were performing on balconies or roof decks out of my sight. For the most part the musicians were passable, especially if you were drunk. Some were excellent, and a few were so poor that I don’t think I’ve ever been drunk enough to enjoy. Being Key West, the principal tunes were Jimmy Buffet and Reggae. There was a smattering of County thrown in as well. The 12 block walk down Duval Street reminded me of walks down Bourbon Street in The Big Easy.









All 15 States Completed

The Cumulative Totals

Miles 3,087

Feet Climbed 90,581

States Visited Maine, New Hampshire, Massachusetts, Rhode Island, Connecticut, New York, New Jersey, Pennsylvania, Delaware, Maryland, Virginia, North Carolina, South Carolina, Georgia, Florida

For more details on my route, see my Strava Link

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