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A Caribbean New Year's Adventure! Part I

What follows below is a true short story I wrote as a chapter in a leadership and teamwork book I have in the works. It's only a rough draft, but since today is New Year's Eve and three years to the day since this event, I figure I will share it with you. This is part one of a three part miniseries regarding what is perhaps the craziest night of my life and how I almost died.

(This picture was taken three years ago today)

How much trouble could two young strapping men possible get into on a tropical island. Well as time has countlessly proven, a lot of trouble with very little effort.

One of my good friends and my number one adventure buddy goes away to Saint John’s Virgin Island for New Years with his family every few years and this year they invited me along. Seeing how we live in Boston and it’s the dead of winter I begged my wife, then girlfriend if I could go on the trip. She was busy with work and school and my friend is single so it would be rude to stay with him for a week and have him third wheel while I take my girlfriend on a romantic tour of the island, when I was invited along purely to go on one of our crazy adventures.

(This is a picture of Ram Head, it's the destination we are trying to reach later in the story).

You see, this trip took place before and is the main reason since attending numerous climbing, survival, and leadership schools. Humble beginnings breed senior success, and at that time, we were winging it. With that said, whenever I go into the wilderness with anyone else we stick to a pre-determined plan with plenty of gear and a meticulously thought out path with contingency plans and plenty of checklist before heading out. Checklist are an essential part of planning. If you go through a checklist, you cannot forget anything. Yet, when this buddy and I team up we usually follow a trail into one of the many wildernesses of New Hampshire for a few miles then randomly decide to turn into the woods and bushwhack into the forest until we find a destination that sounds interesting on the map. We don’t use any trails, just pure dead reckoning with a map and compass through the woods.

There was one time when we were hiking through the Pemigewasset Wilderness in New Hampshire and came across a moose graveyard littered with bones. After leaving the graveyard where I saw about half a dozen moose skulls the size of my ribcage I became paranoid and began hearing a “whooshing" sound pass by me as I walked through the woods. This continued off and on until I was walking through some dense pines or hoping over some rocks and logs in a brook and lost my compass. After retracing my steps back and forth for about twenty minutes we realized we were in shit because there was about two hours of sunlight left and we didn’t have a compass.

Whenever you venture into the woods, especially the wilderness where the chances of someone randomly stumbling by (while you’re still alive) are scarce at best, it is best to take one compass for every person in the party. You never know if someone is going to get injured or separated from the pack. It is always best to have your own map and compass. Now I always carry two.

Without our compass, we attempted to stay on track lining up one tree to the next as we make our way through the woods until we reached a trail. This is known as dead-reckoning, when you shoot a bearing towards a terrain feature and move towards it. The feature can either be a tree a couple hundred meters ahead or a mountain miles away depending on the density of your environment and where you are heading. This is an advance method of land navigation and unfortunately, at the time I was not yet in the Army and was not very good at it. It seems easy in theory, but when you are trying to travel miles without being more than 100 meters left or right of your objective, it’s harder than you think. It is a perishable skill that takes practice. This stood as a reminder that in theory, theory and practice are the same, but in practice, theory and practice have nothing in common.

Back on the trail, it looked as good a spot as any to take a break so we drop our gear and had some raw hot dogs, the lunch of champions. A few minutes later we put on our packs and continue along the trail hoping it will bring us somewhere we recognize on the map. We didn’t travel more than 200 meters before ending up at the exact lake we planned on spending the night. If that’s not luck, then I don’t know what is. Well, except for the amazing bouldering act we pulled off under a full moon on Saint John’s Virgin Island, but that’s for later in the story.

Looking up in the sky I figure we have about two hours of sun light left and my buddy sees a small waterfall about three quarters of the way up a nearby mountain that he feels obliged to climb. Without hesitation, we decide to dead reckon up the mountain until we reach the waterfall then climb up the rocks on the side of it and pitch our tent for the night. Easy enough plan, right?

Well, getting through the dense trees on a 60% incline wasn’t too bad, but after attempting to climb up the waterfall, we realize there is no way we are climbing up that wet rock with these packs on. My friend decides to leave his pack with me and climb up to look around the top. I remind him the sun is now setting so hurry up. He takes off up the wet rocks and out of sight, and that’s it. I call his name and no answer. I didn’t see him fall off the rock and tumble past me so I assume he made it to the top and I wait for him to return at the swampy bottom of the waterfall.

A good amount of time passes before he comes skipping across some tree roots saying, nope, there is no way up there with those packs and no way down without them. He had to go all the way around and back down a trail.

Now we decide to sprint the remainder of the mountain to the top and pitch a tent before sunset. Onward we go, with no time to spare we restart our trek. I’m taking extra big steps up the bounders and slanted rock trying to make good time, only looking back to make sure my buddy is still with me. Now if you have ever played sports, a musical instrument, or programed in IT, then you have most likely experienced flow. Flow is otherwise known as being in the zone and ohh boy, did I enter the zone heading up the trail that evening. I propelled up that rock and the entire trip felt like a matter of minutes. It wasn’t until I reached the summit and looked back at my friend that I remembered I was on a sponsored road racing team and he wasn’t. My bad, as he’s drenched in sweat. He’s an astonishing climber, but I have the lungs.

The top of the mountain isn’t that great. It’s covered in short pine trees and brush with about a 12-18 inch wide trail so we quickly realize we have to go back down to a clearing on a slab of rock and set up camp. As the sun is setting we get the tent up and the burner going. Hot dogs were for lunch, and canned chicken fajitas were for dinner (I am not a minimist).

While sitting there watching the sun set into the distance as we dangle our legs over the cliffs edge taking in the vast amazement of the view before us, I can see a few lights miles away in the distance from what must be the closest town. This view is worth more than a five-star hotel on Park Avenue. Fluffy pillows are nice, but a slab or rock to sleep on and countless mountains as far as I can see, now that is a getaway.

That’s when I hear it. The same whooshing sound from earlier. Only this time my buddy hears it too and points it out first, mentioning he has heard it since this afternoon. Now that I know I wasn’t paranoid after the moose graveyard, I am wondering what followed us from there?

We both jump up and back up towards the cliffs edge, my buddy with the pot of chicken fajita stew and me with my totally unnecessary (except for right now) bowie knife. as we listen to the pine trees in front of us rustle back and forth with some wild animal. In my mind, I’m ready for the spirit of a blood thirsty demon possessed moose to jump out and tear me apart. Then just like that, the noise stops. Enough time goes by and we decide it’s safe to go to bed. Besides, if it decides to come back we have a millimeter of tent to protect us.

(Home for the night on top of Black Mountain)

Chapter 2

Now that you have an idea of how we travel, back to the main story on the island. Looking back at our tropical island trip, it’s no surprise the events of the upcoming adventure still play over in my mind on a regular basis years later. I now understand how things went so wrong, but at the time I was not thinking logically, but rather with my heart.

It all started with a girl. Not my girl, or my friend’s girl, but a random girl that my single friend and I crossed paths with while snorkeling at one of the beaches who captured his interest. We were exploring the area when we came across a nerf shark while searching for sea turtles and he wanted to point it out to her. Being a chivalrous gentleman, he called her over to the shark to take a look.

She tagged along figuring she would have a better chance at finding sea turtles as a group than on her own and agreed to venture through the woods to a more secluded snorkeling area to look for turtles. As if following a couple of dudes around the backside of an island in the middle of nowhere wasn’t already a little sketch, she decides to come over and look at the shark we found.

As the day drifts towards twilight we are heading out when I cross paths with a Barracuda. In a jolt of excitement, I yell for my buddy to come over, he, the great friend he is comes over as quickly as possible, just in time for me to hand him my camera and take a picture of me with the Barracuda. Seeing the fish’s teeth grin at him as they protrude out of his mouth from mere feet away, he says enough is enough and the three of us head back inland.

That evening we all go grab ice cream in the town center then grab drinks at the sandbar. I’m taking it easy since last night was New Year’s Eve and I decided to drink Christmas Trees in the Caribbean. What I mean is I had my fair share of gin and was paying for it tonight. Last night, while wandering around looking for something to do in downtown Saint John’s on New Year’s Eve we stumbled across a couple of young locals who explain how their old beat up boat is part of their “International Global Tours Company” or something like that and hand us a business card they probably had made online for ten bucks.

We figure it seems legit enough for us and hand them $40 and jump into their boat to Jost Van Dyke for what is considered the Caribbean’s biggest New Year’s Eve party. On our way across the bay, I text my friend back home, “just got into a skiff with some random dudes, they are taking us to the biggest New Year’s party, if I go missing check the ocean.”

Chapter 3

Upon arriving, two police officers are waiting at the dock and we don’t have passports (Jost Van Dyke is a British Virgin Island so technically we need to go through customs), but no worries, the boat owner hands them…I mean shakes their hand and off we go. Running off, they yell to us what time we want them to pick us up. We say 3:30am and they agree. We weren’t planning on them waiting, but it was worth a shot. As President Eisenhower said, “plans are worthless, but planning is everything.”

When the fine gentleman of International Global Tours said this is the party of the Caribbean, they were not lying. It’s about a mile of sandy outdoor bars and partying like you wouldn’t believe. It also happened to be yacht week down the Caribbean so there was plenty of celebrities around including rumored to be Kenny Chesney at Foxy’s, but we never saw him.

As sure as the night turns to morning, our skipper and first mate were waiting for us at 3:30am when we finally made it back to the dock. Only, about twenty other people were waiting to pile onto this skiff. We all squeezed on and the poor motor squealed as we head off into the sea.

About half way home the engine gave out. Apparently, we were overheating, so we had to let it sit for a few minutes before we could start it up again. Once they got it going we would go about fifty yards before the thing shut down again. This stop and go process went on for about two hours in what should have been a thirty-minute ride. But eventually we made it back and I was sound asleep in my bed.

(The view from our random boat ride to Jost Van Dyke on New Year's Eve)

(Apparently I took this picture as proof, I was there)

New Chapter 4

Fast forward again to the beach bar the next day, I am nursing a beer and there happens to be a cast of Beauty and The Beast on the island for a New Year’s show and of course Gaston and I have an Alpha male standoff that last about two hours, consisting of corn-hole, pounding beers, and other foolish endeavors which is fine because my friend is too distracted playing Corn-hole with the girl we were snorkeling with earlier.

Last call rolls around so we decide to kill one more bucket of beers before heading back for the night. As we are being driven back home my buddy invites the girl on a leisurely hike down a trail through the center of the island the next morning. She obliges and says she will meet us there 8:00am.

After taking a short nap (probably shouldn’t have had that last bucket of beers), my buddy and I eat some quick chow and head out with two sandwiches, one apple, two bottles of water, snorkeling gear, and my waterproof camera. We decide to leave our phones behind because we already have a camera, why else would we need them.

We head to the bottom of the mountain our villa is settled on to wait for the girl. After about an hour waiting, she doesn’t come so we decide to venture on without her. The trail head is about a mile down the road so we hug the sides of the winding roads praying not to get hit by one of the hundred miles per hour taxis. Once on the trail we head to the Petroglyph pool which is supposed to be beautiful according to the locals and the tales were true, the place was stunning.

The trail turns to dried up river bed where we must leap across small boulders to make our way through. It’s nothing challenging but makes an otherwise monotonous stroll fun. The hike is short and easy since we planned on having someone we don’t really knows fitness level with us. Our intent wasn’t to get anyone killed.

We pop out at the other end of the trail by a small plant sanctuary. I have since tried looking it up online but have had no luck. After eating some jelly substance my buddy identified from one of the plants (he has taken classes on identifying plants) we walk down the roads past a small pond with an iguana chilling beside it because hey, it’s a tropical island. Things are going smooth until we come to a dead-end street with these two crazy dogs. I’m a dog person and I have had a Rottweiler which one of these dogs was and have no problem with big dogs, but these dogs were mean. They were growling and showing teeth, so we back up slowly until we are forced back up the hill we came from. We notice a small trail so we quickly decide to head down the overgrown and narrow path so we can get out of the dog’s sight. It works, but after about half a mile of hiking we end up who knows where. That doesn’t matter, wherever we are is prime snorkeling. I don’t know why but there is no one else in the water in this giant bay. It must be our lucky day!

Strapping on our gear and diving in without looking, we start swimming out at an angle against the current until we are away from the shore and the ocean bottom looks about 50 feet deep. The waves are huge and keep rolling in so we decide to head back in with the current and allow them to pull us along like a roller coaster as we scan the ocean floor for interesting wildlife.

The current grabs hold of me and drags me along much quicker than I anticipated. Gears quickly shift from a doggy paddle in the tropics to my arms and legs moving in a frenzy attempting to dodge underwater coral columns as the water I am now in is pulling me parallel to the shore in a much shallower area. After weaving between columns and having to abruptly stop with my feet by doing what appears to be a sideways superhero landing to blunt the sharp impact with my flippers and avoid cutting up my hands on the sharp rock, I finally reach calmer waters.

After allowing what happened to sink in, I look for my buddy who is a few feet away and we decide, who wouldn’t want to experience that again! So, we swim back around the current and repeat the process a few more times before getting bored and head on shore for lunch.

We each eat one of our sandwiches, because our brilliant planning figured that’s all young men on an adventure need to pack. We hold off on the apple in case we get hungry later and need a snack. After having a few sips of water, we decide to walk east along the rocky shoreline picking up interesting rocks along the way.

(Snorkeling at Saint John's Island)

Chapter 5

Hours go by as we walk along the southern side of the island filling up our string bags with small rocks and washed up dead white coral when we finally have to do a little bouldering. Bouldering is literally the act of climbing over boulders, but I like to think of it as more lateral climbing than traditional rock climbing. Both methods of climbing involve going up and over a rock ledge, but bouldering generally involves more lateral movement and no gear.

Now, I can hold my own indoor rock climbing and my buddy is the best climber I have ever met for an amateur (I haven’t met that many people for the record) so I begin looking around and enjoying the uniqueness of these rocks when I notice speckles of green, orange, and red in the rock. we get around the rocks no problem and continue on our way past a family of surfers just sitting on their boards watching the sun sit low in the sky outside their estate up an escalator into the cliffs. Must be nice, they must be here for Christmas and New Year’s. Fate would have it, these are the last people we see for the remainder of our journey.

Being adrenaline junkies with a soft spot for adventure, my buddy and I continue along the orange cliffs that slowly start turning from speckles of orange to full orange, to green, to black, then to white, with patches of mixed colors along the way. We have never experienced nature appearing this radically and it begins to draw us in. As Lewis Carroll said in Alice and Wonderland, “curiouser and curiouser,” we continue down the rabbit hole or in our case much cooler rainbow of rock formations that have been molded by the ocean into the most unique natural statues and doorways arches I have ever seen.

Man could not have created structures as unique as the rock formations we were climbing over, around, and through. The formations were otherworldly, reminding me more of something from a science fiction movie landscape than a plane ride away. It always amazes me how we spend so much time looking at pictures of places that are only a few hours away by plane. The way we set up our screen savers to rotate through tropical islands such as Kauai, Bora Bora, and the Bahamas, it’s hard to believe people when they remind us these locations are within a day of travel.

While being awestruck by the natural wonders before our eyes, we kept following the entrapment of the coast, failing to notice the sun setting over the rolling waves. But that’s ok, we have been climbing for roughly four hours so we must be close to a beach we know near Ram Head, which is a massive peninsular jetting out into the water and should be recognizable from our location once we get close. Once there, we hope we can pick up a taxi or at least hitch a ride back into town.

We press on, picking up the pace forging our way through small tidal pools, threatening to wash us into the ocean as we grab on tightly to each other’s forearms so neither of us gets sucked away in a rip tide. Tip-toeing over ledges with salty water soaking our sneakers and loosening our grip on the rocks. At this point, the water has softened my hands and my fingers are starting to become irritated by the sharp rock. This is taking a toll on my minimal climbing ability, but my friend and I have an unspoken no complaining policy during times like this. We have no problem vocalizing our opinions at a bar about what our favorite seasonal brews are, but out here, opinions should be carefully delivered to make sure we don’t come off as a wimp.

One time back in New England, the two of us decided to hike a mountain in the winter. It had been hovering in the single digits for a few days and there was plenty of snow on the ground that was acting almost like ice as we were forced to put on crampons and use our ice axe during certain sections of the what is normally considered a long yet straight forward hike because of the hauling wind and slippery surface.

When we arrived at the bottom of the mountain that morning the car thermostat read zero degrees Fahrenheit. We checked the mountain weather and gust of up to sixty miles per hour were expected at the top. So up we went. When winter hiking or mountaineering one of the key things to remember is never sweat. There is a saying, if you sweat you die. Remembering this, we slow down our pace after we get on the incline of the trail and undo some layers, letting out the built-up heat.

As we approach tree-line which is the point where trees stop growing on a mountain, we take one last break looking around at how peaceful everything is in our protected area. After a few minutes rest and tranquility looking out at the peaceful trees and bright sky in the comfort of our tree line, we put on our balaclava and googles and head out to the summit.

Now, I have run about six marathons at this point and as I mentioned earlier, hiking up New England mountains is no problem. Yet, once we went around that corner out of the cover of those trees, it was like we entered another dimension, the Wind Zone. It wasn’t snowing, but it appeared to be as we attempted to dig our crampons into the ice for traction. About one hundred yards of this exposure and I felt like I was in the middle of a marathon. My energy was zapped! Keeping both hands on my ice axe and digging it into the snow like I was on a full-scale expedition, I was taking it one step at a time as I led the way up what I thought was the path.

Once at the summit I took off my goggles and balaclava for a moment to look around and take in some fresh air, my beard instantly froze, becoming frost over so I could barely see shades of light seeping between the frost. It was like frost covering a beer can in a commercial. After taking off my gear, the moisture from the warm micro-system I created under my face gear made my face ideal for frost. I quickly put my gear back on but my goggles kept icing over. Cleaning them was useless, immediately after putting them on after getting rid of the frost they would frost back up again. So, I decided to stay close behind my buddy and follow him back down to tree-line.

Going down the mountain I was paying specific attention to our path. Spending a good deal of time trail running has taught me to always be aware of my path so I can turn around and follow it back out if needed. Well, I could sense we weren’t on the path we took up the mountain. Although my sight wasn’t so good, I knew something wasn’t right. I throw off my goggles and yelled “Stop!” Apparently, my buddy’s goggles frosted over as well on the way back down, but rather than speak up and say something he drove onward. Onward towards the ledge of a cliff. We stopped about eight meters from the edge, from that point on we speak up when we think something is seriously wrong.

Back in the tropics, night eventually settles in and my buddy decides to find out if he can make it to the top of the 50-foot cliff and see what is on top. Watching him scale the loose rock as he goes higher and higher up the cliff, I realize, this wasn’t our brightest idea. Bouldering across solid rock is one thing, but bear crawling up almost vertical loose rock and rock dust, while no one has any idea where you are is another story.

Under our current circumstances, this idea was towards the top of our worst ideas ever list. After only a couple of close calls, he finally makes it to the top and searches for a path, he reports back down that all that is there is extremely dense forest with no path in sight, and the last thing we want to do is be wandering up there in the dark, make an accidental U-turn and veer right back off the edge of this cliff in the dark. It would be like back on that snow-covered mountain all over again. So, we make the call and he heads back down to the shoreline.

(Top of Mount Lafayette, negative 40 degrees)

Check back next week for part 2 of 3!

Always improve,


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