Driving to Key West: Bucket List Item Checked!

The day started later than any day over the past week and a half, with a 7:45 am wake up! In our defense, we didn’t get in until 11:00 pm last night and our dinner, Pizza Hut Supreme (once again in our defense, the only thing open) did not come until 11:45 pm. I ended up falling asleep with my glasses on we woke up to a beautiful morning and got ready and were checked out, coffee in hand, in the car ready to go by 9:30 am for our 3 hour drive ahead of us. Almost 10 years ago my coworker, Jean, told me how amazing the drive was on the Overseas Highway to Key West. It has been on my bucket list ever since. Later, I found out it was also on Derek’s list. Today, we are both crossing that off our list.

The gateway to Key West and what connects the Florida Keys is the Overseas Highway. According to Wiki “U.S. Route 1 : The Overseas Highway is a 113-mile highway carrying U.S. Route 1 (US 1) through the Florida Keys. Large parts of it were built on the former Overseas Railroad, the Key West Extension of the Florida East Coast Railway. Completed in 1912, the Overseas Railroad was heavily damaged and partially destroyed in the 1935 Labor Day hurricane. The Florida East Coast Railway was financially unable to rebuild the destroyed sections, so the roadbed and remaining bridges were sold to the state of Florida for $640,000.”

“Since the 1950s the Overseas Highway has been refurbished into a main coastal highway between the cities of Miami and Key West, offering travelers an exotic roadway through a tropical savanna environment and access to the largest area of coral reefs on the U.S. mainland. Many exotic animals such as the American Alligator, American Crocodile and Key Deer inhabit the tropical islands of the Florida Keys.”

“While the Overseas Highway today runs along the former Overseas Railroad right of way, portions of the highway came into existence earlier in a different alignment while the railroad was still operational. The concept of an Overseas Highway began with the Miami Motor Club in 1921. The Florida land boom of the 1920s was underway and the club wanted to attract tourists to easily reached fishing areas, which could only be reached by boat or train at the time. The land boom also attracted real estate interests who sought vehicular access to the upper keys where there were thousands of acres of undeveloped land. The completion of the railroad further proved a highway through the keys was feasible.”

In the summary above it says in one sentence “Completed in 1912, the Overseas Railroad was heavily damaged and partially destroyed in the 1935 Labor Day hurricane”… HOWEVER there is much, MUCH more history in that sentence. I read a lot of this and was fascinated and shocked, I had no idea, I will definitely be reading more about the history, but here is more if your interested from Wiki and KeyHistory.org: “The first Overseas Highway was formally opened in 1928. When vehicles reached the lower end of Lower Matecumbe Key, through traffic had to board a car ferry. The service provided by the car ferries was slow and unreliable. Equipment failure and too-shallow water were the primary problems. To serve passengers waiting for the car ferry, a cafe was opened” (Later, the Ferry Slip Cafe would be replaced as the Toll Gate Inn.)

“A project was initiated to bridge the water gaps with bridges as permanent as the railroad’s in order to eliminate the slow and unreliable ferryboats. In 1932, World War I veterans had marched on Washington, D.C. demanding to be paid their WW I service bonus. One solution was to send these veterans to construct a bridge over the water gap between Lower Matecumbe Key and Jewfish Bush (Fiesta Key) Key” (part of The New Deal).

The principal Veteran’s work camp was just west of the Lower Matecumbe ferry landing and the Ferry Slip Cafe and the other on the northeast end. Each camp housed some 250 men. A water desalination plant was built at the lower one to provide fresh water. The desal plant had been tested, approved and was ready to be accepted by the government when the Labor Day Hurricane struck on September 2, 1935. Other than debris, the only things left standing on Lower Matecumbe Key were the two water tanks. All buildings were destroyed. There were no civilian permanent residents on the Key at that time. The Key was once again silent except for the rescue teams.” Photo Credit: http://www.keyshistory.org/Bridge-that-never-was.html

In all, 40 miles of railroad track were destroyed, but all the steel and/or concrete bridges were undamaged. All that remains today of them are the decaying concrete bridge piers and a dredged island that is now known as Veteran’s Key. The piers remain as a tribute to the veterans with a memorial plaque on Craig Key. Photo Credit: http://www.keyshistory.org/Bridge-that-never-was.html

“Of the over 400 fatalities from the hurricane, more than half were veterans and their families. Their deaths caused anger and charges of mismanagement that led to a Congressional investigation … The full highway from the mainland to Key West was officially opened for traffic on March 29, 1938 and upon completion, the route became the southernmost segment of U.S. Highway 1, which previously terminated in Miami. President Franklin D. Roosevelt toured the road in 1939.” The Labor Day Hurricane of 1935 Memorial. Photo Credit: findagrave.com

I wished I would have known all this before our journey as I would have appreciated it more – but that’s why I’m sharing! We also should have done more research on what to do once we got to Key West and especially where we should stop on the way but we have been moving so fast this trip and didn’t even think about it until we got in the car 🤦🏼‍♀️ but luckily we have internet and we found an article about where to eat along the way: CNN also had an article about where to just stop along the way, we sadly did not have time for these but will definitely be back!!

We decided to stop at the Tiki Bar at Holiday Isle because it looked like it was right on the beach and Islamorada was also in the CNN article about a “must see” town. I’m so glad we stopped as it later would be our favorite place from our entire weekend in the Keys.

We arrived at the Tiki Bar to find that it didn’t open until 11 so we grabbed a drink next store at The Postcard Inn + Raw Bar. This place was my paradise!!! It has everything I look for, right on the water, bar and restaurant on the water, live music, fire pit, beach area with swimming and paddle boats and more to use!!!

We learned that this area was completely destroyed by Irma and had JUST been rebuilt and opened two weeks ago!!

Giving advice I would DEFINITELY suggest staying here one or two nights on your trip to Key West. After our drink, we ventured to the Tiki bar for some famous Rum Runners. This place was super cool as well and definitely worth the stop!

We left a signed Colombian pesos to hang and continued on our way

Locations along the Overseas Highway from Key West to Key Largo are commonly given as mile markers. Numbering starts in Key West, and increases towards the east and northeast up the path of the highway over the keys. We are staying steps from mile marker zero!!!

Businesses along the highway began listing their locations by mile markers, adding decimal parts to more precisely indicate locations between mile marker signs. The numbering pattern is as follows:

  • The first three (or four) digits denote the approximate mile marker; the first two (or three) digits denote the mile while the last digit denotes the nearest 0.1 (tenth of a mile)
  • The last two digits denote a particular address; an even digit denotes an address on the Atlantic Ocean side while an odd digit denotes an address on the Florida Bay/Gulf of Mexico side As an example, the Tropical Research Laboratory of Mote Marine Laboratory has a physical address of 24244 Overseas Highway. The first three digits indicate that it is near mile marker 24.2 (corresponding to an address on Summerland Key), while the last two digits indicate that it is located on the Atlantic Ocean side of the highway.

We talked to some locals on the drive down who said the rebuilding has been long and hard and is still going on. We talked to a local coffee shop owner when we stopped for a much needed shot of caffeine. He was originally from San Diego but lived in the mid-west for many years and then moved down here 6 years ago. He said he didn’t enjoy living here and could not wait to leave 😬 he said it’s hard to find love in a place that’s only industry is hospitality and service. He hadn’t been on a date in a couple years 😥 he also mentioned there is a pretty big drug problem here. It was an interesting perspective.

Coffee Shop Owner’s Cat

We continued on…driving the next couple hours on the Overseas Highway was not only beautiful but really exciting. It’s like a prolonged feeling I always get when coming into a beach town for a vacation. A highlight and maybe what I think of most when I think of my childhood is spending every other year on Ocean Isle Beach in North Carolina. Coming into the beach town each year was my favorite part, going over the huge bridge to the island and all the anticipation that came with it. The drive to Key West was hours of this exciting anticipation for the fun and beauty that lay ahead.

We arrived around 3:00, perfect timing to check into The Cabana Inn (which had chickens roaming outside) but then Derek let me know Key West is sorta known for their chickens. According to the Florida Rambler “There have always been chickens in Key West. When people stopped the laborious process of turning live chickens into Sunday dinner many decades ago, some backyard chickens gained their freedom. Other roosters were released when cock-fighting became illegal.” Read more

After checking in (and not being impressed with the service of the front desk staff) we put out bags down and were out to take our time getting to Mallory Point to watch the sunset. The hotel was nice and in a great location, which is most important, but the staff was just not friendly or helpful.

On the way to watch the sunset we did some shopping and visited some amazing art galleries. The shops reminded me a lot of Wisconsin Dells in Wisconsin with iron on t-shirts and lots of similar souvenirs in every store.

We arrived at the very crowded Mallory Point just in time to find two lonely spots at the bar, grab some drinks and watched the spectacular sunset.

Two lovely ladies offered to take our picture and it turned out great! The last sunset of our adventure 😥

After the sunset we went to try and find the Mojito Man per a suggestion from a friend on Facebook but had no luck. We decided to get dinner at Carolina’s (shared a burger as we were both feeling fried American food after two weeks without it) and of course finished our dinner with the famous Key Lime Pie. We were then off to bar hop along Duvall Street.

We hit all the places Derek’s friend, Tony, recommended: Captain Tony’s (the original Sloppy Joe’s), Sloppy Joe’s, Irish Kevin’s (live video streaming Temple Bar in Ireland, very cool!! Especially since my friend Meg is there), and ending our night at the Margaritaville Cafe with drinks in a blender and more live music. Live music was everywhere we went! That was cool as there was variety at every place and made every place a little different.

Every place was fun, but it definitely was more of a party scene than what we were used to. Almost like a mini New Orleans. We also noticed that most people were from the midwest or the East Coast. Interesting- probably because it’s so far from the west coast. This place would have been a dream for me to escape the Iowa winters and a somewhat inexpensive flight if I remember correctly.

We did ourselves proud and made it to midnight and decided to walk back to our hotel- drinks in hand! Yep, just like New Orleans! What a long, beautiful, entertaining day!!


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