Before we get into any detail about the madness that took place, I think it is best first to give everyone a little background on how this came to be. A couple of months ago I ran into Adam Killgore, and we got into a conversation about where I hailed from, the Cayman Islands, and that is was endowed with one of the sickest concrete parks in the world, The Black Pearl. After consuming enough alcohol to put a small elephant in a coma we agreed that we would keep in contact about getting some heads down here to bring rolling back to the Caribbean. Several months later it was a done deal, tickets were booked and paid for, a hotel right on the turquoise blue Caribbean Sea was booked, and Adam Killgore, Ross Anthony and JonJon Bolino arrived in the Jewel of the Caribbean.

Thursday July 26th: Their flight arrived around 1:30pm. You could see that they were tired from the night before plus the journey itself. Also, you could see that Ross and JonJon were both confused as to why some strange island person flew them down to this island paradise, but at the same time excited at the fact it was done. Adam was just ready to rock out like a pop star! Before we got into the whole island lifestyle of drinking and swimming on the beach, we stopped by the Black Pearl to give them a sneak peak at what was to come. After the shellshock at the sheer size of it, everyone got crazy-juiced just to strap on their skates and skate it but it was too hot. So we ended up doing the next best thing–going to the beach, downing some food, and having a couple of drinks… all while the three of them ran in and out of the water. JonJon was already eyeing the island honeys, but it was later learned that he has no game except for rolling.

From the beach we went back to the hotel then headed off to the park. Now keep in mind that this park has never been skated by rollerbladers of this caliber before. 99.99% of all the park’s patrons are skateboarders, and some of them had never seen people rollerblade before, never mind people that could actually rollerblade well. Nevertheless, all the kids there were chill as hell and welcomed the new “Pirates” of the Pearl with open arms.

Due to the size of the park, the first day was pretty much Adam, Ross and JonJon just rolling around the park trying to get a feel for how it rolls and picking out spots where they could lace some tricks. That didn’t stop JonJon from landing perfect 720s and 900s– first try might I say! This of course got the locals asking him to do more flips, spins, and a wild assortment of other tricks that would put you and I in the hospital.

When the sun set on the first day it was back to the hotel. Everyone got cleaned up, and we went to the hotel bar/restaurant to get something to eat. Ross decided that he would get exotic with the food and ended up eating some conch fritters, which he said was the weirdest thing he had ever tasted, then began to drown the taste with several Cayman Lemonades, a real tourist drink. JonJon was just shocked that he could actually sit at a bar and order alcoholic beverages without being asked for an ID or given a hard time. I think he made the most of that. After that we got into a fierce game of Dominoes in which beginners luck kicked in and I got my ass handed to me. So it goes. We didn’t really do anything much after that as everyone was pretty beat up from the day so we just called it a night.

Friday July 27th: We got started around 11:00am and since it was crazy hot we said F–skating ‘till the afternoon. Instead we went out exploring the island. The first stop we made was a little cove on the west side of the island that provided some wicked views of the west coast, along with the opportunity to take some pictures of the ocean, beach, fish, etc. Then we headed to Cayman’s very own Turtle Farm which Ross dubbed Turtle Town! It’s a breeding ground for endangered species of turtles where you can feed them, pick them up, take pictures with them, and also swim with them. They also have a man-made salt water lagoon and a predator tank with sharks and whatnot. Once again JonJon kept looking at the lovely assortment of female flesh, but did nothing about it.

After Turtle Town we went to this spot on the beach just to do some swimming and kick it. Adam and Ross found these 16 year olds from Texas but it turned out that they were wearing big glasses for a reason–to hide their faces! JonJon was just walking aimlessly up and down the beach looking for an alleyway he could try and take a cat back to, but once again failed to perform!

From the beach we went to this local jerk chicken hut to eat some real jerk chicken pork and my man DenDen came through for Adam. I think this was when Adam’s island experience began! We also tried to get JonJon to eat a Scotch Bonnet pepper for CI$1.00 but the lady would not let him for fear he would start crying.

After our meal we went back to the Pearl to have a session before the night’s festivities began. It was pretty tight that some of the little skateboard kids were actually sporting some of the Denial and Dub Caesar shirts that Adam gave out the night before. I can’t really remember what happened that day at the Pearl expect that Ross, JonJon and Orrie, a local roller, decided to play a game of “OUT” during which Orrie busted his knee open trying a switch darkside fishbrain. We ended up having to end the session and take Orrie to the hospital to get stitched up.

When we were done with the stitches, it was back to hotel to get ready for the Shaggy concert that was happening that night. We met up with some of my friends at this local bar called Breezes which overlooks the harbor and began to consume Mojitos, Red Bull and Vodka’s, Rum and Water’s and Jah only knows what else. After about two hours there it was off to the Shaggy concert in which Ross began to get Boombastic on everyone at the show. It didn’t matter if you were man, woman or monkey, Ross was grinding on you! I am shocked he didn’t get beat down but then again it’s nothing but love in the islands. JonJon’s game came out a little when he started dancing with the infamous Moustacheio! I’ll leave it at that. Adam was just wilding out with The Dan who kept telling him to spark up and as soon as he would kept telling him to put it out. I think that lasted the whole night. I would go more into what took place but really I can’t remember. I do remember that JonJon fell off the bed when we went back to the hotel but that’s about it.

Saturday July 28th: For some reason I woke up crazy-early on Saturday, I think it was like 8:00 am or something dumb like that. My head felt like I did an acid drop and landed on my head. I don’t think Ross or JonJon were feeling too hot either. It was all laughs though when we started to remember what actually took place the night before.

That day we headed off to Sting Ray city for the guys to try and pull a “Croc Hunter” by swimming with sting rays. It was a pretty cool experience for them until one of them puked on JonJon’s back. I thought it was funny but I don’t think he did. After Sting Ray city we headed towards the east side of the island where Ross managed to capture a pink ring to float on that allowed him to swim around with jelly fish and star fish alike.

When the boat ride was over we went back to the hotel to get cleaned up and head to the Pearl by 5:00 pm because the night before I was telling everyone that I knew to come and watch these people roll. I think I must have told around 200 people. Well, we ended up getting to the park a little late and it seemed that everyone that came to watch went inside the bar to escape the heat and stayed there drinking. Ross was rolling all around the park putting together some sick lines and at one point in time landed a 360 to soul. Then he started to attack the ledge from a different angle where he did a 360 to rib cage plant. That was it for Ross for the day. JonJon on the other hand was landing abstract 360’s to disaster souls to cab out into the bank along with some other crazy things that I will just leave out for now. You will have to get the team video to see what else took place.

After skating we were all pretty beat so we just went to the bar by the park, got something to eat and pretty much just passed out. The Dan wanted us to go to Peppers, this local club, but there was no way we would have made it.

Sunday July 29th: Sunday is a chill day here in Cayman. Pretty much everyone just heads to the beach somewhere, or heads out on their boat and takes it easy, and that is pretty much what we did. We headed up to the east of the island to this place called Rum Point where everyone was playing tourist. Ross and JonJon were swimming around and Adam was just checking out the local scenery. We stopped by this local gift shop where they were able to get some snorkel equipment since they wanted to know what was swimming underneath them. Leave it to Ross to get the pink one. Personally, I wouldn’t be surprised it he dyes his skates pink.

From Rum Point we went to this local Sunday hang out called Driftwood to get some BBQ and Mudslides. After eating, Ross went adventuring out by the reef. He was starting to grow gills by this point in time for being in the water so much. The rest of us just chilled out really, listening to music, hanging out, and whatnot. Like I said, Sunday is a chill day down here.

Later that night we went street skating in the streets of Cayman. First spot was next to a church where Ross did a HUGE 540. Then we went to a supermarket where they had some flat rails that Ross and JonJon started skating. All I will say is that JonJon is like a human video game. You just say “do this” and he does it. From there we went to these tiled ledges for a little session before heading to these red drop rails that JonJon was hell-bent on skating. I really have no idea why he wanted to do them because no one ever wants to skate these things.

Monday July 30th: Monday was pretty much the last day for the three of them here in Cayman since they had to leave early the next morning. To make matters worse, we had to wake up at like 7:00 am since we agreed to do a radio interview that morning on a radio station that my friend Serlina works for. She was way too awake for me that morning, and I think the rest of them, too. Not even the Red Bulls we were downing before the show brought us up to her level. It was all good though; we got to talk about the trip, Adam, Ross and JonJon all got to talk a little about rolling and what it meant to them and we also got the hook-up for potential sponsorship of the next rolling event here in Cayman.

After the show we walked around the capital for a little, checking out the shops. Ross bought a Pirate Flag, JonJon got a ”Peter Meter,” and I’m not sure what Adam got. I know at one point in time he was looking at a CI$55,000.00 watch.

Then we went to “Hell,” so they could check it out, and also send out some postcards. Real tourist stuff.

From Hell we went to this beach up the west side of the island to swim on this reef. Adam saw a Barracuda and that was pretty much it for him. I don’t think he went back in the water there again. JonJon was chilling on the beach, again drooling over the abundance of female flesh that was surrounding him, but was not able to seal the deal.

From that beach we went to another beach bar/restaurant for some lunch and just haung out. Adam and Ross were snorkeling around while JonJon was busy looking for his mask and snorkel that had somehow come off his head and sank to the bottom. No one is really sure how that happened. After lunch and Adam trying to woo our waitress Jessica by singing “Baby Girl” to her we headed back to the hotel where Adam and Ross came up with the brilliant idea of snorkeling naked just to say that they did it. I still say that it’s pretty gay. What do you think? It was also kind of confirmed when Ross let is slip that he was comfortable with his homosexuality! He was just playing kids, so don’t take that seriously…

Once they got out we headed right to the Pearl for their last session. All three of them were skating just like monkeys on crack. Adam was the first one to bust out with an AO Top Porn to Back Farf 270 out and it was all up hill from there. Each and every one of them kept trying to out do the other, either with the lines they were putting together or the tricks they were trying on the various obstacles around the park. I must say though that Ross did one of the most stylish parallel 540’s I have even seen. I would have to say though that the trick of the day went to JonJon who did this crazy wall ride on the Black Pearl wall. Even now I can’t put my mind around how he did it.

At the end of the session all the kids at the park were excited to try rolling, so we took off our skates and let them roll around the park. Ross gave away his helmet to one kid, but he couldn’t sign it for them as requested because we couldn’t find a marker. JonJon was ready to give his skates away but instead I did since two kids that said “they liked rollerblading more than skateboarding” fit into my skates better.

When all was said and done you could see that the kids at the park were actually sad to see the three of them go. The kids gave all three of them their props and told them to come back to Cayman again to skate! As a rollerblader I must say that it was a moving experience.

Since it was their last night here on the rock I figured I would send them off “island style” and what better to do that than a bonfire on the beach. The Dan and I collected the beverages, Orrie dealt with the firewood, and it was on. We got there around 8:00 pm or so by which time Ross turned into a 65 year old Snoop Dogg sipping on Gin and Juice. Adam was just sparking left, right, and center and poor JonJon was so beat and tired from the trip he didn’t know what do to with himself. At one point in time he feel asleep in the car and in hindsight I think I should have left him in there because once Ross saw him it was over. Ross’s main objective was to get JonJon to join him in the water one last time and even falling in the fire didn’t stop him. Thankfully he failed. By the end of the chase Ross was covered head to toe in sand, and I am sure there is still some in my car. The bonfire lasted ‘till around 4:00 am, so we were all so tore up that the last thing anyone wanted to do was stay awake, pack, and head to the airport. The Dan was left in charge of Ross to make sure he got back and all packed while Adam, JonJon and I tried our best to make sure that they didn’t leave anything behind. p>

5:00 am came around and it was off to the airport. We pulled up, said our goodbyes, and then off into the terminal they went. I can only imagine the trouble Ross must have caused on the flight back. All in all, I must say that having those three down here were one of the best times of my life. Those five days are filed with memories that will last a lifetime. In closing I would just like to say THANK YOU to Adam, Ross and JonJon for taking a risk and coming down here. You are more than welcome back anytime! And I also extend that same welcome to anyone that wants to skate the Pearl.

Until then… BULLET BULLET BULLET!

Jonathan Martin A+, Network+, CCNA