Key West FL – My first overnight road trip on a motorcycle

March 28-29, 2017

Key West was a road trip that my BF and I had been wanting to go on since we started wintering in Florida eight years ago. 

It just happened that the opportunity would arise when my BF’s best friend and his wife came from Germany to visit with us for two and a half weeks. 


We took them to as many ‘touristy’ attractions as we could think of, keeping it to within a days outing. Eventually we started running out of places to take them, at least places that were of interest to them.  So, when the idea of a Key West motorcycle road trip came up and everyone agreed, I could hardly contain myself, I had also been having severe motorcycle withdrawals for over a week by this time. 

Key West obviously is not really that close to us, but is very doable as an overnight road trip. If it were not for the expense that our friends had to endure with a bike rental, and how expensive it is to stay in Key West we might have stretched it into taking in an extra day. None the less, I was stoked about riding out there and jumped at the chance to ride the famous Seven Mile Bridge.

We planned all of it in less than a week prior to leaving, maybe a bit short notice but surprisingly between reserving a motorcycle rental from the Harley Dealer in Fort Myers for our friends and securing a room in Key West, we had no problem getting everything set for the date we had decided on. After scouring the Internet looking for a decent place to stay in Key West I found the Southwinds Motel and it was only a block from Duval Street. The reviews were good, and the price was as reasonable as one could get for being in Key West. I had heard about how it was cheaper to stay outside of Key West but the whole point of going there was to be where the ‘action’ was and as close to the famous Duval Street as possible.

The road trip begins, Tuesday March 28

That morning the weather was perfect, however a slight chill in the air had me putting the liner in my jacket and wearing my hoodie. 

It was going on 9 am by the time we got ourselves and our bikes ready for the road. My BF took the lead, and I ended up in the middle of our trio. Normally I always like to ride in last place when it is just the two of us. 
It was a straight forward ride to get there from our location and instead of I-75 we opted to cut through Big Cypress National Preserve on US-41. Obviously the more scenic route with plenty of interesting stops along the way.

Route to Key West – 265 miles one way

Lucky for us US-41 was open again, just a week before, the road was closed due to a wild fire. (The fire had actually started on March 18th) Over 25,365 acres in the Big Cypress National Preserve had been ravaged with the fire. 

The BF & I 

Along US-41 we had to stop and show them the Little Post Office.  The Ochopee Post Office is the smallest operating Post Office in the US. This would be my third time here, but it was a definite “Must See” for our friends and we happily obliged.

Our friends at the Little Post Office

Next stop was at Turner River Road, where the HP Williams Picnic Area is located. It is usually an excellent place to see alligators, at a safe distance along the boardwalk. However none were to be found when we were there. 

compliments of Google Map

After we left we crossed the bridge just after the park and it was my BF who had spotted where all the alligators had gathered. We all immediately pulled over for the photo op.

finally some alligators to photograph

It was a little ways after we had stopped to take the pictures of the alligators that I noticed where the fire had gotten close to the road and seen the burnt-out palm trees that had a blackened ashy look to them, at least the ones that were left standing. The grasses were an odd rusty brown colour that contrasted with the bit of green leafiness that was poking through all the devastation. 

When we stopped for gas at the Miccosukee General Store, that was when I noticed how the coolness of the early morning had been quickly replaced by the hot humid air and it wasn’t even close to midday. Time to take off my layers. So far there had been next to no traffic and the ride was invigorating. 

Filling up

There was quite a bit construction turning onto FL-977 and continued for several miles, even though the traffic had increased at this point, it really didn’t cause too much of a problem and flowed at a steady pace. This whole area has a large concentration of farms and tree nurseries.  FL-997 brought us through the town of Homestead and directly out onto US-1.

Visitor Center – Key Largo

Me

After crossing the bridge over Lake Surprise we made a stop at the Key Largo Visitor Center. It was just nice to get off the bike for a bit and gulp down water. 

My first impression of Key Largo was that it reminded me of a tired community that had weathered its fair share of misfortune, although I could only make this assumption from the road I travelled. In all fairness we did not spend any amount of time there and didn’t explore any part of it. 

I guess it was sometime around 1 pm at this point and we all agreed that our stomachs were growling. 



At least for my BF and I an outdoor patio is a must when it comes to dining in Florida, what is the point of being in a sunny warm place and be stuck indoors with air conditioning – which by the way I can’t stand, I literally freeze my a$$ off in air conditioning, well it feels that way. 

Keys Bite

Anyway, from the road, my BF caught sight of such a place with a nice patio, Keys Bite in Key Largo. Shhh, just between us… my BF actually turned a bit early and into an entrance of another business prior to the restaurant, I guess he didn’t feel like turning around and getting back onto the road so we followed him riding our bikes on the paved walking path over to where the restaurant parking lot was. The food was okay, standard roadside eats, but then again, I am not much of a ‘foodie’.


Islamorada, FL
Passing through Islamorada my BF motioned to the Giant Lobster sitting in front of The Rain Barrel Sculpture Gallery. I was already turning in for the photo op of my first bonafide Americana roadside attraction. 

Giant Lobster

(I have been training the BF to recognize anything that might be photo worthy – it was finally paying off) 

As we headed out I took in the sights from the road, and liked how the tall palms lined the road. I could have probably spent the rest of the day stopping at all the curiosities that were stationed in front of various attractions and businesses. But I wasn’t riding alone and we still had about 2 hours or so before we got to the motel, so I resigned myself to just enjoy the ride and besides I didn’t want to push my luck. 

Marathon, FL

Observation Area after bridge

Marathon had that ‘big city’ feel to it and we stopped for gas just before the Seven Mile Bridge. The plan was also to stop for our photo ops just before the bridge, but as we approached the exits were blocked off and the observation area was closed. 

So, suffice to say we couldn’t get the before pictures of the bridge, so onward we went. 

Iguana taking in the view

I must admit the view from the road was spectacular! That blue green tone of the water melding with the bright blue sky. What a feeling riding over that bridge! It surprisingly went fairly fast and before I knew it we were already on the other side. When we got to the other side we pulled in to an observation area. 

Looking out from the observation area

Key West, FL

Front of Southwinds Motel

As we pulled into Key West it was sometime after 6 pm and the traffic was heavy as it filtered onto the island. The further we went eventually the traffic thinned out a bit and then we turned onto a quiet street and checked in to our motel, the Southwinds.  


The room was clean and compact. It fit the four of us comfortably to sleep, we were only there to crash for the night anyway. 



We opted to share a room to cut down on the expense. ($280 for one night!) However, it was my kind of motel, I only like staying where you can access your room from an exterior door. (just a quirk of mine I suppose)

Out front of our room

View from the deck

Our room

We unloaded the bikes and our main priority was to go across the street to the Deli and Grocery store (Ana’s Cuban Café) that we had caught sight of when we pulled into the motel.  

Much needed, ahem...beverages

I had the trade mark ‘biker burn’, at least I wasn’t alone, we all looked like raccoons. 

mmmm, beer...

Resident Rooster of Motel

The first thing I noticed were Roosters, they seemed to be everywhere and just wandering around. I knew Key West was noted for its colourful community and interesting characters, and famous for its large community of artists, but Roosters? 

That warranted further investigation… 


I later found out that the birds have called Key West home for almost two hundred years. Early pioneers had initially brought them over as a source of meat and eggs. Then in the 1950’s when Cubans fled the Revolution they brought even more of the colourful birds with them. Unfortunately, it was mainly for the Cock-fighting competitions that were, in my opinion, a gruesome part of Cuban culture. Thankfully that became illegal and seeing there was no longer a need for individual families to keep chickens with the advent of markets being readily available, it all contributed to a population explosion within the chicken community. So, it came to be that the birds gained their freedom and were just set free to roam the streets as they pleased, which by the way earned them the fitting name of “Gypsy Chickens”. 

A quick night on the town…

Mission accomplished - The BF & I

It was going on 7:30 pm by the time everyone took their turn in the shower to get the days road dirt washed off.  For me, it was imperative that if I were in Key West that I had to go to the Southernmost point and have my picture taken. It was also the consensus of everyone else. It was just a 5-minute walk from the motel, probably more like 15 given my turtle pace. When we got to the monument there was still a lot of people who were gathered there. At least people were polite enough to wait in line and take their turn at the huge hunk of painted cement. 

Our friends

We headed up Duval Street and I realized Key West is truly a world of its own, and I suppose that made Duval Street the epitome of all that is unique and unusual. There was plenty to gawk at while walking along, what caught my attention the most was the beautiful historic buildings that lined the street. Of course, that probably had something to do with my door obsession that I have. As the sun dipped the restaurants, bars and cafes filled up and the night took on a life of its own. 

There was the odd drunk person, case in point -  one woman was recklessly riding her bicycle down the middle of the street weaving back and forth. She disappeared around a corner and we never saw her again. Most of the shops pedaling the usual tourist fair had their doors wide open encouraging one to come in and browse.


The most popular mode of transportation besides walking were bicycles and scooters, but even a few golf carts could be spotted zipping around. It was strange to see that there were very few actual cars on the street. Bicycle taxis also joined in the throng as they travelled up and down Duval providing a relaxing way to get around while allowing one to enjoy the evenings tropical breeze. 


A Collection of Sights From the street…

Looking up Duval St.

Weather Station

Margaritaville

My BF and I had built up going to Margaritaville in our minds since we had started coming to Florida for the winter. We even adopted the Margaritaville song by Jimmy Buffet as ‘our song’. All we could think of is going to the Margaritaville Restaurant and having dinner or at least a few drinks there. 

When we finally got to it, it just wasn’t what I had built up in my mind at all, nor was it very appealing to my BF either. In a way, it was a bit of a let-down. For some reason, I was expecting a beach bar, which is stupid because I knew that Duval St. is not directly on the beach…. where I got that idea… oh yeah, the song, and the images my mind would conjure up when I heard it.  I guess at the very least we thought it would have a wonderful outdoor patio. The shock of how it actually looked busted both our bubbles and we didn’t even venture in to a have drink.  I just stood outside the open window feeling bewildered and snapped a couple of pictures.

At this point it was going on 9 pm and we were all starving. We walked across the street and stopped at a place called Willie T’s. The fact that it was basically a covered patio was what drew us to it the most. 

As we ventured closer I noticed money had been stapled on the walls, ceiling, practically any free space available. It certainly got my curiosity stirring and I asked our server what the scoop was with all the bills.

The Dollar Wallpaper started as a way for people to leave their mark at Willie T's by signing the bills with well wishes and quirky sayings. Soon it turned out to be quite the attraction and turned into around 70,000 - 80,000 dollars being tacked to the walls at any given time within the restaurant. Once a year Willie T's takes a wall or two down to donate it to charity.

The beer was ice cold, a live band played, and the food was great, at least for this non “foodie” and extremely fussy eater, my Chicken Tenders were delicious. Everyone else seemed to enjoy their meal too. 


For “normal” people, it probably would have been about a 15-min walk back to our motel, however I am not “normal” and I walk extremely slow, (could be because of my short legs) so it probably took a lot longer. By the time we did get back to our motel it was well after 11 pm. I think everyone was well past their “expiry date” and instead of a night cap we flopped into our perspective beds.

Wednesday March 29

The next morning we were up early, well I especially was. I even managed to be awake before the Rooster. We had a full day on the road ahead of us and our friends rented motorcycle had to be back to the Harley dealer by 6 pm. It was already getting steamy and I didn’t even bother layering under my jacket with my hoodie and opted to even leave the liner out. The motel offered a free complimentary continental breakfast which we decided to wait for, it started at 7 am. I had brought my own tea bags, (my strict rule of my tea needing to be Red Rose) lucky I did, I had never heard of the brand they offered. Anyway, I ate a half plain bagel, it was just too early and I couldn’t choke down anything more at that time in the morning. 


After checking out of the motel we took a ride up Duval St. It certainly was deserted at this time of the morning. No doubt that the party animals were still fast asleep in dreamland. We stopped at the dock at the end of the street to have one last look.  Then we were on our way around 8:30 am. 

A deserted Duval Street

Looking out from the dock

We took the last of our photos of the keys at Tom’s Harbor Channel after crossing the 7 mile bridge.

Tom's Harbor Channel

We stopped for gas in Marathon and there were even Roosters walking around there - I think they were migrating from Key West due to over populating. <wink>

While the bikes were getting filled up I happened to catch this Iguana run across the entrance, no worries he made it.

By the time we stopped for lunch on the outskirts of Homestead, I was already heat exhausted and tired. Even the thought of taking pictures eluded my weary brain. All I remember now was that it was somewhere on 997 and was a Cuban Restaurant. The only thing that does stand out for me with this place is that I recommend not ordering the Chicken Fingers, unless you like frozen chicken parts rolled in a not so flavorful coating. (Note to self, be leery of a place that still calls their chicken tenders, fingers) At least the fries were edible. However, everyone else seemed to enjoy what they ordered, and the portions were very generous. Side note, it also had a small patio, bonus point for that. 

I have to admit the ride home didn’t have quite the same pizazz to it, in fact hitting the open road and feeling that allure of “freedom” for the ride had diminished as the exhaustion of the past day travels took its toll. I am sure that having an extra day would have made a world of difference to my current feeling on this. The worst part was that my already sun burned face was now reaching 3rd degree burn status. 

“I realized at this point that I will probably never
enter any Iron Butt competitions.”

We stopped only to refuel the bikes and ourselves, but for the most part our sight-seeing portion had run its course and I think we were all in ‘hard core’ travelling mode.   

Our last rest stop was back at the HP Williams Picnic Area on 41,  I was very grateful for the restrooms that were provided there. From there we went non-stop back to 82. We only pulled off on 82 for a short break to part ways while my BF and friends continued on to Fort Myers to return the trike. (To be clear, another friend of ours was picking them up in his Van, my BF didn’t want them to ride alone to Fort Myers being unfamiliar with the area) I on the other hand headed home alone and was glad my travels had come to an end, at least for this time. 

Follow up…

Ouch! My sunscreen just didn’t cut it. Lesson learned I went out and bought a 60+ sunblock! 

Would I do a similar ride again, you betcha, in a heart-beat. 

Wonder what I can check off my bike-it list next….

Reference:

Florida Rambler 

Key Westing