Background: Ladies, gentleman, and those yet to decide, hello and welcome to my first ride report. This is also the biggest trip I've taken since getting into traveling long distance. I'm super fortunate, because when my fiance and I watched the Long Way series, she said "can we do that?" So this trip is essentially a step towards that, although I went solo because she has a job she needs to be present at. I work remotely, so traveling while working is doable. If we can pull off what we want to, in the future her, my best friend Marek, and I will travel the entire world for 3-4 years Ted Simon style. I guess for some, there is an elephant in the room. The motorcycle I've chosen to do the trip on, a Triumph Street Scrambler instead of a cushy adventure bike. For two main reasons. 1.) I love the motorcycle and it's a joy to ride. 2.) It's the only motorcycle I own right now, unless you count Caitlyn's Suzuki S40, but I definitely didn't want to do it on that. Other than that, the only other things to know are that I have a remote job in the music industry that I can work from anywhere as long as I have cell service/wifi Monday thru Friday. So I worked up until Seattle, where I took vacation to continue north. Also I live in New Orleans, so I figured I might as well start in Key West so that I could do the Iron Butt Association's Ultimate Coast to Coast. For those who are into visuals, I have an instagram @scramblerstories and a YouTube channel, also Scrambler Stories. The whole trip was filmed and will eventually be up on YouTube, but probably not for a few months considering I'm still on the trip currently. If all goes as currently planned, when we do the RTW trip we'll have weekly videos. Enough of a backstory? I think so, let's get on with the ride. Getting to Key West Technically my trip started on Thursday, May 9th. You see, originally I was going to trailer the bike down to Key West and start fresh there. Caitlyn was going to come with me, but unfortunately due to an injury a few weeks earlier, she couldn't afford to miss work. So instead of renting a truck/trailer, I figured I'd save the money and just ride down there. I can push myself quite well, and long mileage days aren't an issue, even if they aren't the most enjoyable. Because of the nature of my job, most of my traveling would have to be on the weekends. Which meant hanging out places to work on the weekdays, and vast miles on the weekend. On that Thursday morning around 8am, with my bike packed and butterflies dancing in my stomach, I departed New Orleans. It felt much like Long Way Down, in the sense that I would be back in the Big Easy by Sunday night if everything went as planned. This gave me roughly a 2200 mile test before continuing on. I had fresh Metzeler Tourances on, and I had just changed my oil. I would be replacing the chain once I returned. I think I was somewhere around 23-24,000 miles on my bike. Everything else was in order. I was bringing a three gallon Rotopax strapped to my bench seat, even though I wouldn't need it for the first few days. I wanted to get use to having it. Riding Thursday went well. At my first gas stop, I busted out the laptop and worked for a few hours from a Love's Truck Stop. Eventually I gassed up and continued on until I needed gas again. Same drill, busted out the laptop and worked. Eventually my work day ended and I was able to ride into the evening. All day I was constantly on the edge of storms, however I never hit rain. Just some strong winds which do take on a toll on a naked bike. I rode into the night until I was pretty tired, and figured I had done well for a first day. Stopped at a Motel 6 in Ocala Fl, 566 miles from my apartment in New Orleans. I stayed at this hotel when I got Caitlyn's bike from Miami so I knew it was clean, and not expensive. The staff let me park the bike outside the lobby so they had an eye on it. Perfect, I could leave my camping gear and the extra gas on the bike. I slept, and in the morning I started work from the hotel room. Close to checkout time, I took off. Bound to pass through Orlando, and perhaps see a friend in Miami on the way. I thought about stopping at the Ace Cafe in Orlando, but I didn't have time and wasn't sure how cool it would be anyway. I'd rather go to the original in London. I had decided also to take the risk of not wearing my jacket, and went with a t-shirt and a vest instead. Perhaps not the smartest move for a pale dude. Despite generous helpings of sunblock, I still ended up sunburned. Also, I wasn't aware of Love Bugs in May. 91 south of Orlando was quite populated with the bastards. The giveaway was the car sprayers at the rest stops on 91, which I had never seen before. At one of my stops, I could barely see when I pulled in. So I got gas, food, checked emails, and most importantly cleaned my visor. Yup, I also took advantage of those sprayers because I was covered in Love Bug death. Eventually I continued on. Unfortunately a few minutes down the road I came to a stop. Traffic wasn't moving. I sat there like a good boy scout for a good 15-20 minutes, but it was hot. Too hot for an exposed human... Eventually I decided I needed to move or I would get sun stroke. So I made my way to the shoulder and bypassed about a mile of stopped traffic. Eventually I came to a lot of people hanging out and asked them what was up. They didn't know, but they had been waiting for awhile. I engaged with a gentleman about lane splitting because he made mention that I had ridden in the shoulder illegally, when suddenly cars began to start moving. So I obliged myself back into the line and joined in. Eventually we passed a wrecked Harley, and now the stopped traffic made sense. The rider wasn't around so I don't know the condition, but since traffic was completely halted, it may have been a fatality. Not a good feeling to know we may have just lost one, especially on such a big trip with it's own dangers. I hoped for the best, but at best looked like some serious injuries... It wasn't the last wrecked Harley I would see in Florida. After that accident, there was another not far down the road. Eventually I would get up to speed and continue on to Miami. I got to the outskirts of Miami Friday evening, so I'll allow your imagination to picture the traffic I experienced. Miami has terrible traffic to begin with, but Friday evening heading towards Key West was probably the exact wrong direction to be heading. I stayed legal and didn't lane split. Again, I'm hardly a badass. Also, my bike wasn't legally registered. I had an expired Tennessee registration, and I was struggling to get my bike registered in Louisiana. When I went to do it, I was informed that my financing company was purchased by a new one. My attempts at getting a copy of the title for the DMV in New Orleans was futile. The 24-48 hours the title department would get back to me was a lie. They wouldn't get back to me after multiple attempts, but I decided to continue and hope I would get it sorted by the next week. At some point the gods of traffic took pity on me, and it thinned out as I got on route 1 heading for Key West. I was behind schedule, and since I was camping (way cheaper than hotels in Key West) I was hoping to be there while there was still some light. I also badly needed a cold beer, as I was starting to notice how sunburnt I was. The plus side is I was riding through the Keys as the sun was setting. Suddenly it felt like the traffic had done me a favor, because damn that was beautiful. Sunrise/sunset might be the best time to be riding through the Keys. I was awestruck, and naturally wishing I could share that with every soul currently in existence. Figured I would record it, I was filming this trip after all. Turned out to not be a good idea. For one, I put the GoPro in picture mode, not video. The Sena 10c on my helmet isn't the best quality, thus why I wanted the GoPro on my handlebar on. In the process, whether I didn't mount it properly or I hit it just right going for the GoPro, I ejected my phone from the Quad lock mount I had just added to my handlebars. There went my phone at 50mph. I went back for it and recovered my iPhone 8 plus, but whether it fell on the screen or got run over by one of the vehicles behind me, it no longer had a useable screen. The phone still worked, but I'd have to answer incoming calls via the Sena headset, cause I couldn't do a thing with that cracked screen. I missed my turn for the campsite (Boyd's Campground) and ended up stopping at a hotel. I saw a Starbucks and was hoping I could use their wifi to lookup a map on my laptop, but they just closed. So I walked over and asked a girl who appeared to have a smart phone. She honored my request, and I as surveyed her friends came over. They were playing a scavenger hunt and asked to kiss my head since I shave it bald. Fair trade off so I allowed it. Hopped back on the Triumph and made my way to the campsite. Checked in, and I had a spot on the water that faced east. Perfect for the sunrise so I was happy. Ground was too rocky for my stakes, so I threw in gear to weigh the tent down. It was already night, but I had a headlamp on, turned out to be a useful purchase. Didn't think I'd need it unless working on the bike at night. Once setup I went over to the game room area to use the wifi. Wanted Caitlyn to know I was alive, but now without a working phone. I charged it anyway, so I could answer if she called (provided my helmet was on). I do have a replacement plan through Apple but once looking at their Miami locations, I figured I was better off getting the new phone in Naples. Easier to find my way there without GPS. I really wanted that beer, but it had been a 460 mile day while also stopping to work, plus some sun abuse, so I decided I just wanted to get some sleep. I'd get a beer as soon as I could, it was time to prepare for the beginning of the 30 days I had to get to Deadhorse. Day 1 (officially) Saturday May 11th I woke pretty early since I didn't bother with my flysheet. Weather looked favorable and it was. The thought of waking up to a sunrise was appealing. I did have some work to do even though it was a Saturday. I also had to print some forms for the challenge, as I would need the signature of a police officer in Key West. There also was a few other riders around that I got into conversations with. Including a couple on a BMW K1600 that looked super comfortable... I got a later start than planned, but eventually I was fully packed and started riding around Key West. I got gas which gave me my official start time, then I made my way to the "Southern Most Point" for a photo. I meant to do this around dawn so there wasn't a line, but whatever. I waited in line for 30 minutes and a couple helped with my photo/video. Then I rode around looking for a police officer, which proved to be harder than expected so early in the day. They're everywhere at night, naturally combatting the night scene. After riding around for awhile, I stopped at a liquor store. I wanted to buy something and bring it all the way to Deadhorse to celebrate with. They didn't have anything "top shelf" in a small bottle, so I went with some Jameson. It is one of my typical choices anyway. Asked the guy where the police department was, and he pointed me in the right direction. It's slightly off a main road, so I had ridden past it a few times. Got my signature from a rather cute police officer (she's married and carries a gun, don't bother) and I was on my way. I had planned to stop and get external shots with cameras for the Youtube, but I was not far enough along as I had wanted to be. Instead I flew on, with the trumpet not breaking a sweat. I got to the mainland and had semi memorized the roads I had to take. Pulled over at a McDonalds and used the wifi from the parking lot (woot woot, technology!). Ah, I missed a turn because it wasn't labeled. Memorized my next few turns and continued on without needed to eat anything from there. Since I had already taken 75 through the Everglades when I did a fly and ride for Caitlyn's bike, I wanted to take route 41 instead. Stopped to get gas and asked the cashier but she had no idea. Probably hasn't left that area. She's young, I hope she explores the world one day, because as many of you probably know, she's missing out. I was right, and found 41 west without issue. It was a nice ride, though not exciting. Hoped to stop at Joanie's Blue Crab Cafe (learned about it on Ride with Norman Reedus) but it appeared to be closed. No worries, I was starving since I hadn't ate yet, but I also wanted to get to the Naples Apple store before they closed. Continued on and discovered that the Naples Apple store was closed for renovations anyway. Damnit... There was a Chipotle near by, so that would suffice since I didn't get what I wanted. I got my semi healthy taco bowl, used nearby wifi to contact Caitlyn, and finally got that beer I needed. I'm a bit of a craft beer snob, and yes New Orleans has some amazing beers despite being known as a cocktail city. However that Bud light I had certainly tasted amazing at the time. After eating I continued on, my goal being Oscala at the same Motel 6 I knew was cheap, but clean. After riding through the night, I did stop at that Motel 6. 526 miles on that Saturday. Again, the same place I had stopped when getting Caitlyn's bike. I knew at that point although it was later in the night, it was also May, so I shouldn't have an issue getting back to New Orleans by a reasonable time to catch Game of Thrones. That's right, total nerd here, did you think I was cool or something? The massacre of Love Bugs... Riding through the Keys during sunset. Photo at the expense of my phone... The camp site on the water. As per the challenge rules, took my photo with the southern most point. A fire road in the Everglades.