After being trapped in The Dry Tortuga’s due to weather, we finally saw an opportunity to skirt over to Key West. We left at sunrise, and due to the weather conditions, we expected to be in Key West in 12 hours. The seas were still a little rough but nothing like the previous day. It was still too risky to go out on the deck, so Nick and I stayed in the cockpit for the whole sail. We took naps, talked about anything and everything, ate pasta salad that we had made a couple of days before, and enjoyed each other’s company. I had many “K.R.T.” moments which you will learn translates to “Kelly Random Thoughts.” If you know me, then you know this is something that happens frequently and on a daily basis. Call it my artistic brain making strange connections between random things and I blurt it out! It makes Nick laugh while giving me a crazy “where did that come from look!” It’s par for the course when you and I are in a conversation.

When we made the turn into Key West Harbor, we heard one of our friends “2nd Unit” calling Tow Boat US. Unfortunately, their fuel filter was clogged, and they were unable to use their motor. They got to Key West around midnight, and we pulled in around 10:00 pm. Ohana was shortly behind us and rafted up with us in the City Dock. We all freshened up a bit and went to Duval Street. The primary objective was to head to Irish Kevin’s, but we stopped at Sloppy Joe’s to check out the band. It’s always a great time there! We finally made it to Irish Kevin’s, and it did not disappoint. Dwayne (one of Ohana’s crew members) bought us all Irish Car Bombs. As you can see in the video, it didn’t go down so easy for me. When I tried to finish it, it was like paste! That was my first one, so I call it a rooky mistake haha! As we started to head back to the boat, there it stood…the ultimate street food, Pete’s Meats! After a couple of drinks, there is nothing that tastes better.

The next day, I had a flight at 6:00 pm. That gave us time to have some brunch then hang out at Dante’s poolside bar for the afternoon. We sipped on margaritas and enjoyed the sunny day. When I got in the cab, I literally had tears in my eyes. I didn’t want to leave! The trip had proven to be one of the most memorable of my life. I realized at that moment how lucky I was and how much I looked forward to starting our cruising life.

After I left, Nick is forced to make a tough decision about how he gets home. His brother and family happened to be vacationing in Fort Myers Beach so they could easily hop on the Key West Express. However, Ohana and 2nd Unit were leaving the next day, and Nick could sail solo alongside them. I didn’t like that idea because he would have to keep watch all night by himself! We talked about it, and he decided to go with the first idea. I also gathered a few friends to make the drive down with me so we could sail back to St. Pete with him. Nick’s brother and nephew met him in Key West. They hung out for the day and left the next morning. The sail to Ft. Myers Beach is 24 hours.

Stay tuned for the next episode to see Nick’s 24-hour sail with his family while myself and friends meet him down in FMB!

Video Transcription

Intro (Key West Sailing)

We’re all going to Dante’s. (Key West Sailing)

Sailing into Key West (Key West Sailing)

We lost a little protection from the Tortugas reefs so now this is what we’ll get for the next few hours. See how this feels, winds picking up, might have to reef a bit more on that mainsail. What’s for lunch? More pasta salad, right out of the bowl, a little too rough for too much else. What do you think? Just a little corner. Feels a little bit better. How has your day been? Not worth it, it’s too salty now. So we’re gonna pull into Key West at like 10:30. Do you have any aspirations of going out in Key West tonight? Yeah. Party on Wayne. India is weird with their time. (Key West Sailing)

Arrival (Key West Sailing)

This is what you do in Key West when you roll in unannounced on Spring Break weekend; you raft up at the city dock. Luckily it’s calm. Ohana and Satori joined as One, United. (Key West Sailing)

Dante’s Pool Bar (Key West Sailing)

Ah, yes. Dante’s pool bar at the Conch Harbor Marina. Open to the public, this is a great place to grab a drink and have a swim. Especially after a long sail. Since Kelly only has half a day before she has to fly back for work, we made the best of it. Take care of this girl. Damn clouds. What a thing to have to bitch about. We get a picture of the all-star talent. He’s the guy behind the scenes. Yeah, for sure. (Key West Sailing)

King Arthur (Key West Sailing)

The Adventures of King Arthur. Look at King Arthur as he summons his servant to fetch his most prized possession, a one-of-a-kind bottle of golden lather. A good king has a weakness for anything gold, a weakness that could easily be exploited. Watch as his so-called trusty servant takes advantage of his highnesses state of euphoria. She douses him with water straight from the frigid depths of the sea. He tries with all of his heart; he cannot escape the shock of this betrayal coupled with his malignant fear of water causes his body to shake uncontrollably. Not since he was a young pup has King Arthur found himself so helpless. By the time our King comes to, the servant is nowhere to be found and neither as his gold. Hmm. (Key West Sailing)

Monday Morning (Key West Sailing)

So it’s a Monday morning, yeah Monday, in Key West. Kelley left yesterday. Trying to get back to St. Pete eventually and deciding when I leave. Do I wait to try to get my brother down here to help me sell back or do I leave with these guys on the crew? So, making that decision today. Also, gonna clean up. Let’s call it a little bit messy from the trip. The second unit needs some help getting their engine back running because they got towed in by Total US Saturday night and they have some battery issues as well. So, get them up and running because they need to get back too. So, a lot of stuff to do today, decisions to make. (Key West Sailing)

Battery Repair (Key West Sailing)

Before I do anything today, some Cuban coffee. About to go meet Jeff and Art, deal with this battery situation. Those don’t look too good. 2012 though, we got four years out of them. Yeah, almost five, you taught me that. (Key West Sailing)

Help Arrives (Key West Sailing)

All right, Miah and Kagan are here. These guys are here; they’re gonna help me sail the boat back to Fort Myers Beach bright and early in the morning. Oh yeah. Yeah. But first, let’s take a walk down Duval Street. This is Kagan’s first time in Key West, so we had to show them around a bit. Duval Street is the famous downtown corridor that connects the Atlantic Ocean on the south to the Gulf of Mexico on the north side of the island. It’s his first time in Key West. It’s packed with a vibrant collection of hole-in-the-wall bars funky shops and plenty of places to people-watch. Are you in a band? Yeah. Keg in the closet Kids E. I like to describe it as Bourbon Street with palm trees although I’ve never been there. (Key West Sailing)

Sailing to Key West (Key West Sailing)

So, we just left Key West. We should be getting to Fort Myers Beach first thing in the morning. Hold up there for a couple of days and Kelly and some other friends are gonna make a trip down from St. Pete, it should be good time excite. Overall, it’s been a good trip so far. Next time on Sailing Satori, Nick’s brother helps him sail out of Key West, and I meet up with Satori in Fort Myers Beach. (Key West Sailing)