April 8th, 2026

For Florida Loop 2026 Day 5 Part Two I continue to roll south to Key West, Florida via US Highway 1 – Overseas Highway.  The riding through the keys in many areas was spectacular, despite some heavy traffic in some of the town areas (with Key West having very heavy traffic).

Day 5 Total Miles (Part 1 & 2) = 221 Miles

Riding on the Overseas Highway to Key West

Except for some congested areas in some of the towns on the route, this is a spectacular ride, especially riding over the longer bridge spans over the ocean with the Seven Mile Bridge being the most impressive.  This is one road I would not want to be on my motorcycle during a storm.

Riding a motorcycle over those vast expanses of ocean (not just a large lake) is very surreal.  The color of the ocean in the Keys was amazing, a very vibrant blue, much more so than other areas of the ocean I have seen Atlantic, Pacific, Gulf.

The weather was very favorable for riding today, not crazy hot, surprisingly not strong wind on the bridges (it had been quite blustery riding through the Everglades today).  I did not find rain again until I rolled into Key West and even then, did not last very long.

Key West

Traffic congestion in Key West was no joke.  Once I arrived and parked Bruce at my hotel, I stayed on foot for the rest of the night.  All those darn tourists visiting Key West (myself excluded of course, LOL).

The vibe in Key West was certainly one of chill and relaxing which of course I had very little time for based on how I scheduled this trip.  However, once I got settled into my room, showered, and threw on some shorts, a clean shirt, and slipped on my Hed Dude soft shoes I use as camp shoes, I was able to join the chill vibe for the remainder of the evening. 

I first went to the (new) Southernmost point of the Continental USA for my obligatory selfie with the buoy.  However, there was a substantial line of people waiting who had the same idea.  So instead, I waited and took a photo of the Buoy itself in between people posing with it, I was not going to wait in that line (I guess I was not that chilled Afterall LOL).  I did take a selfie with the buoy’s back side…. good enough.

From the Southernmost Pint park area, I then walked down Duval Street to Sunset Pier to try and capture the sunset.  I got there a little late but still came away with a few nice pictures.  During my walk on Duval Street, I admired the old architecture in Old Town and stopped and looked around a few shops and purchased the obligatory shot glass when I go on motorcycle tours.  I then walked back toward my hotel on the other side of Duval Street and decided to have a great steak dinner at Viva! Argentinian Steakhouse. 

I really liked Key West, a bit touristy for me for solo travels but I see the appeal and would like to return, but with more time (so I could properly join the chill vibe).  Probably will not ride a motorcycle down here again though as this has been crossed off my bucket list.  I am not opposed to ever doing it again, but it’s not a must do.  Instead, I could see myself and my wife DeAndra, (and maybe Tristan…would be nice to have a husband wife only trip…. it’s been almost a decade since that has happened LOL).  Maybe we will fly into Fort Myers, rent a car and spend a few days around Everglades City, Marco Island, etc.  Then drive to Key West and spend a few nights there.  Either way, I am sure I will visit Key West again in some fashion.