We had a great day of sailing back to Key West. We tacked up behind Wisteria Island (Christmas Tree) to find a calm protected anchorage. It was much smoother than our past experience of anchoring in Key West.

Willow called West Marine and a local prop shop for a quote on propeller repairs. We then decided to stay in Key West to get the propeller fixed at the Prop Doc on Stock Island

We took the bus over to Stock Island to drop it off for repair. They advised it would be ready in two days. Two days “stuck” in Key West. I was excited! 

As soon as we got back to the sailboat, our dinghy engine propeller broke. I don’t know how we get so lucky! We had to wait until Boot Key for repair as the Prop Shop didn’t repair this specific propeller. So, we used Zachs dinghy engine to keep mobility while we waited it out here to leave.

Since we had the delay, Saul and Gegi grabbed a bus back up to Boot Key to secure their boat and prepare for their flight to Panama. After they departed, we all decided to venture around and find a good place to eat. 

Somehow, on our way to find food, we ended up finding drinks instead. By the time we made it to the third location, I stopped looking for food. It turned out to be a great day of exploring. I kept thinking to myself “only in Key West would you find a bar inside of a bait and tackle shop.”

Rabble and Darla made it down to Key West to celebrate Darlas 21st birthday. It was perfect timing! We grabbed some of the best coffee I’ve ever had at the Cuban Coffee Queen and made it to Mallory Square to watch the street performers and join in on the Sunset Celebration. It was great to finally stop in to check it out. One of the street performers added Rabble into his performance, jokingly insisting that he had the hookup for some Shrooms. 

We ended up walking around awhile and heading over to Hogs Breath Saloon to end the night. We got to hear some great live music and dance for a few hours. 

I find Key West to be one of my favorite cities. It has so much history and diversity and just enough craziness to keep you coming back. It has been home to Jimmy BuffettKenny Chesney, and Ernest Hemmingway, who willed his entire estate there to his cats

It’s always 5 O’clock there and you can guarantee to go down almost any street and find yourself drinking when you didn’t plan to, or seeing chickens, or maybe both. If you’re lucky, you may even see a pirate dog on the corner collecting change for his rum addiction! 

I research the areas we sail to and try to get to know the history, while finding different places to explore. Key West not only has great locations but also interesting entertainment. I found this great article to read about Key West, the “War” and the Conch Republic history. 

The next day we were headed to shore to catch a bus back to Stock Island. It was time to plan the rest of our trip back to Boot Key.  On the way to shore, we were stopped by the Coast Guard.

Just as our first experience with them, on New Years, it went good. It just so happened that it was the same officer that had pulled us over that night. He remembered us and was just as respectable as our first encounter with them. 

While I was sure to show him the flares (that we had forgot to include during our first stop) we did forget to add extra life jackets and put the registration back in the Dinghy. 

The officer reminded us that the first question he had to ask was “are there any weapons onboard?”. While I was shaking my head to say no, Rabble did inform him that Darla knows Kung Fu.

He advised us to head back to the sailboat and grab the other life jackets and paperwork. As the first experience with them, they were gone when we got back.

 We not only got our prop and ready to head back to Boot Key, but, found another outboard engine. Willow would have to do some work on it, but we did need a higher horsepower engine for the Dinghy. 

We pulled anchor and found fast that we weren’t going to be moving fast today. The winds weren’t as expected so we had to find an anchorage west of Bahia Honda for the night.  We found a spot which would be close enough for Darla & Rabble to take a bus back to Boot Key to get things prepared for their upcoming trip to the Bahamas.

We rafted the boats together for the night and headed out to find a spot to land the dinghy. We made it to land just as the bus was passing. Luckily, another bus came through a little later.  We made our way back to the boats in hopes of better winds to get us farther. We were ready to complete this trip.


“There’s always going to be the circumstances you can’t plan for. There’s always the unexpected relevance and the serendipity”.  ~Jason Silva