The Dominican Republic Challenge: The Daily Grind

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The Dominican Republic Challenge: To get from San Jose, Costa Rica to the Dominican Republic for an 8 day all inclusive tour of the island, all for a grand total of $500 with no backup funds, and ultimately showing up at a resort in Punta Cana for the wedding of an old friend. After a [...]

Filed Under: BLOG, Best Travel Stories, Posts by admin February 4, 2011, 5:32 pm

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The Dominican Republic Challenge:

To get from San Jose, Costa Rica to the Dominican Republic for an 8 day all inclusive tour of the island, all for a grand total of $500 with no backup funds, and ultimately showing up at a resort in Punta Cana for the wedding of an old friend. After a $340 return flight, I was left with a mere $20 a day.

I set out for the Dominican Republic at about 6 am through the bustling streets of San Jose. An odd time, when the night dwellers and morning crowds meet for an awkward mingle over breakfast. I was to get to the airport for my 8:30am flight but had a very important stop to make first. In order to fly out and back into Costa Rica, I needed to show proof of onward travel. Without a plane ticket, I attempted to buy a bus ticket to Panama for the next week. Sounded like a great plan but the bus companies would not issue a ticket that far in advance. So I was left with no other options and would have to try my luck at the airport.

It has been said before that I have a horseshoe lodged in the darkest depths of my body, although never proven, it has been tested regularly.

I got to the airport to check in and, as expected, the man at the counter told me I needed proof of onward travel. I confidently claimed I had it but not in hard copy. Management got involved and I had to sit off to the side as they tried to figure out what to do with me. I interjected, pleading to use their computer, to show them the ‘copy’ in my email and prove it, in an attempt to speed things up. After discussing and finally believing my bluff, the man actually wrote his personal email down on my plane ticket and said to make sure that I sent him the copy as soon as I landed. It seemed very odd to me but I complied and was on my way to the Dominican Republic. He wrote the email address on the wrong part of the ticket which was torn off and kept by the flight attendant as I boarded the plane. So even if I wanted to, I couldn’t personally email this stranger the fake ticket I didn’t have.

I arrived in Santo Domingo at about 3 pm. I had done absolutely no research, had no guidebook, or a plan of action. So I figured checking out the first city in the new world was a good start. I managed to walk outside of the airport and grab a cheap collectivo taxi, typically a rundown van which picks up anyone they can fit in, and drops them off anywhere they want. My 30 minute ride to downtown was about $1.20. The safest bet for these things is to just say ‘centro’ and being a white tourist, chances are they will just drop me off in tourist town with all the other Gringos. Not always reliable however. As everyone jumped out, I followed suit as it looked like very busy streets and clearly a main area of the city. It was a fairly similar scene compared to the other cities I have been as of late, but with a distinctly more African influence. Cars and motorbikes speeding furiously through each other with no regard for order, vendors lining every inch of sidewalk and selling every possibly piece of crap you can imagine, food stalls constantly waving the flies off their products, hair getting ‘did’ on the corners by impromptu barbers, and people napping everywhere. I began strolling through the chaos in search of a hotel. I knew the direction of the ocean so I took my time heading there assuming I might find some nicer spots. After about an hour of looking at terrible hotels in sketchy areas, and not finding one under $40, I began to think I was in over my head with this rice and bean budget. I soon approached Chinatown, always a great sign, because chances are, you are right in the middle of downtown and will be able to find the cheapest food and accommodation. And they were cheaper, about $35 a night. The shadows of doubt had been cast and lingered around my head like a brewing thunderstorm. I tried bartering with no luck, I tried sketchier areas with no luck. It was then and there that I knew that thunder was not the kind of storm I was stepping into. As I walked on, I managed to stumble upon the colonial district. Shades of vanilla appeared for the first time, American restaurant chains and shops lined the streets, and every local seemed to morph into a ‘tour guide’ offering the best and cheapest tours, hotels, and drugs….yet still nothing under $25. It was a beautiful old city, very reminiscent of Havana and other classic Spanish influenced cities of the old world. I managed to strike a deal with someone and found a tiny little dive hotel for $25/night. I knew I would not find cheaper so I settled for $5 more than my daily budget alloted.

After a little rest and a cold shower, I hit the streets to check out the nightlife. Bars and restaurants appeared from behind metal gates, a young and fashionable crowd took over, and the tourists slowly faded back to their hotels. I found myself having a conversation with Jose, the self proclaimed best tour guide in town. I know better than to humor these guys because there is always a catch, always an end result of my pesos in their pockets. But he was fairly amusing and I was enjoying the banter so I went with it. When he found out I was Canadian, he enthusiastically announced he knew the perfect bar for me. A Canadian bar! “Greg would be so excited to meet you”. What the hell, why not eh? So we walked a few blocks to darker and less crowded streets and stopped at a thick alley door with no signs, lights, or music. A few heavy pounds on the door and a set of eyes shot out from a peep hole that slid open to examine me. It sounded like a bank vault opening, and in we walked to a group of half dressed, giggling ladies sitting on a leather couch greeting us with open…er…arms. The stench of stale beer, cigarettes and the flesh trade punched me in the face. ‘Here we go’, I thought, already planning my escape.

Enter Greg, the 70 year old bartender/owner/pimp/drunk. He greeted me with a creepy smile ear to ear under his chubby red face, and veined nose of a seasoned drinker. OK, one drink I figured. He poured me a stiff rum, and proceeded to tell me about the ‘specials’ of the evening. “I’ll just stick with the rum for now, thanks.” I said, as a stiletto stroked my calf. He ignored me and shouted at Tonya, the woman attached to the stiletto, to show herself to me, like some sort of messed up window shopping experience. I assured him that I believed how fit she was and insisted that I would just have the rum. As I sat there, I got to hear the misadventures of Greg, and how this ol’ son of a gun, came to be the man he is today. It was repulsive and intriguing all at the same time. But on that note, I dried off my ice cubes, paid my bill, politely brushed off Tonya, and left Greg, Jose, and more eagar patrons with their uninspiring night ahead of them.

With such a late start to the first day, I decided to stick out another night and see more of the city, since there were some impressive sites to see. I wandered the cobblestone streets, and took in the sites along with thousands of other camera snapping, fanny packer tourists. I was on the cheap, and so very limited to what I could do. But wandering around for free or sipping a coffee and people watching can be the best entertainment you will find.

With my budget seriously approaching red ink, I had to leave the city. I was already in for over $70 after 2 days. So the next morning I made my way back through the shady parts of the city and found a cheap bus north to a small town called Bonao. But not before my mototaxi pulled one over on me. After driving around the block a couple times he dropped me off at the closest station, not the one I needed, and told me to get off. I said I needed change and he grabbed the $2 in pesos out of my hand, pretended to get off the bike and then gripped it and ripped it, peeling off like he stole something, about $1.25 in fact. If I didn’t think it was so funny, I may have tried to stop him.

The hour bus ride, stretched to nearly 3 hours by island time, cruised through beautiful scenery and up to the highest points in the Dominican Republic. I got to Bonao and hopped on another mototaxi to a very small town along the river and checked in to a quiet and tranquil hostel in the middle of nowhere. Rancho Wendy, an old family run ranch turned hostel, with close access to beautiful hiking trails, waterfalls, villages and coffee plantations. So tranquil, I was one of two guests. The other, a young chap from England touring the island for a few weeks. I spent the afternoon hiking through the villages, and attempting to find the waterfalls on my own, after a series of animated directional pointing and hand gestures from the owner of the hostel, ‘Frank’. ‘Understand?’, ‘not really but thanks, I’ll figure it out, Frank’. This bought me along the river where the children swam and women washed their clothes, through the villages of shy faces, and up some trails through the highland farming. Locals would pleasantly point me in the right direction to my imitations of water falling. Following more and more trail, it became less and less accessible, and finally ended. There was one gate surrounded in barbed wire with a hand painted private property sign, I may have entered if I didn’t see random articles of clothing and shot gun shells larger than swollen thumbs scattered about. So back I turned, and settled for swimming in the river.

After dinner, Matt, the other guest and I took a little stroll into the town in search of whatever nightlife may occur in this place. They do things a little different here. By day, the convenience stores stock their fridges and sell the normal convenient items but come nightfall, tables and chairs come out of nowhere, filling every inch of possible floor space, music gets cranked up to overkill levels, and dancing and drinking ensues. Ever dance and party in a convenience store, at convenience store prices? How convenient is that? It puts a whole new level of convenience in this conveniently convenient convenience store. With such little tourism in these parts, we were welcomed with curiosity and straight faces wondering who the hell we were. But as beers were passed around, guards were dropped, smiles were cracked, attempted conversations commenced, and the laughter and good times that are so universal to everyone were shared. Before we knew it, we were being invited into neighboring huts to use the facilities and being pulled up to dance with big sassy women shaking their oh so revered Caribbean rumps up in our spaces. It was one of the funniest nights on record and I will now look at convenience stores as being less convenient for not utilizing and living up to their full potential. Dear, Seven Eleven….

The next days intent was to make the push to Punta Cana, and hook up with the wedding group. Down to just $30 for the next 4 days, I was completely relying on getting into that resort and not spending any money. Fate would play out in the most crazy ways for me on this day. I cannot explain the weird chain of events that were to come and I can only say that the proclaimed horseshoe was put to the test.

After 5 hours of bus time, I reached Bavaro, the closest access point to Punta Cana. Unsure about my chances of getting into the resort, I had previously arranged a couchsurf for the night. Couchsurfing is an incredible online community of travelers all over the world, willing to help out other travelers by offering their couch for free accommodation. I got off the bus around 4pm and decided to go right to the resort and try my luck, or push my luck rather. I grabbed a quick mototaxi and off we went, cruising through the strips of resorts, looking for any access point to the beach. It was looking grim and security was efficiently watching every point of entry. I got dropped off in front of the resort and walked around for a bit. Unsure of what to do I went for the always risky ‘balls out’ approach and tried the front gate. With no bracelets, it wasn’t a terrible idea. I walked right up and sure enough, he approached. My ‘balls out’ suddenly dropped into the icy waters of Lake Not Gonna Happen. I did have somewhat of a method to the madness, I had previously googled some resorts in the area and wrote one down that was supposed to be beside this one. As he stopped me I scanned around for other points of entry and watched his monitors. I pulled out the paper and said I was actually looking for this resort I had written down. He read it with confusion, and glared at me with stink eye, mumbling in Spanish. He pulled me into the booth and picked up the phone, I tried to tell him it was a misunderstanding and walk away but he insisted, calling the front desk and handing me the phone. My thoughts were flooded with the image of my head on a wanted sign, much like the others on the wall I was staring at. I slowly raised the receiver to my head like a gun, trying to end the misery of this situation. The woman spoke perfect english and with a confused tone, told me that the resort I was looking for, the one I had written down, was actually this resort two years prior. Stunned at the statement, I pretty much had nothing to say. An “oh, no kidding?” followed with an awkward laugh. Thank you Google maps. I claimed a big misunderstanding and would go sort it out. So I walked away with with my head down in shame, and not the normal walk of shame I am used to, but similar in that I did just get screwed. It was getting dark, and being on the wrong side of the gates is not the safest place to be. Since I was now clearly on their radar, I pulled the chute and decided it was not going to happen on this night.

I made my way back to town by way of a few buses and got dropped off at a main part of Bavaro. It was dark, I was alone, not with all of my friends, angry and worried that I had bitten off more than I could chew. With $11 left, I couldn’t even afford a hotel room. So I attempted finding J, my couchsurfing contact. I tried his number a few times at the post office but it was consistently out of service. At this point, my ‘balls out’ had completely frozen over. I scrambled back to the internet to get his address and send him an email in hopes he would get it fast. I hopped on a mototaxi and headed for his place. Cruising through the grimy city, I couldn’t help but think of the woman on the bus telling me to be careful in this place and shocked that I was coming here alone. The directions led us to a large development with no lights, street signs or numbers. We drove around for an hour looking for his place but with no luck. Everyone we stopped to ask had no idea. It was approaching 9pm, I had the wrong phone number, address that didn’t exist, a pissed off driver who was probably debating leaving me on the side of the road, and now $9 to my name, getting into the resort was the last of my worries. And on top of it all, I had lost my sunglasses and a shoe, the right one to be exact. Which had probably fallen out of the side of my bag as we were driving around aimlessly. How was I going to get myself out of this one? Did this guy screw me over? was it on purpose? Was someone trying to bait me to a dark spot and claim my organs for the black market? These thoughts tend to cross your mind when you’re tired, hungry, frustrated, and nervous.

We asked another man, and he thought he knew someone that might be able to help, so we all got on the bike and went to another building. A well dressed Cuban man came out to greet me. He scanned my directions and gave me a confused look, not my first on this day. “This man is your friend?” he asked. I explained the connection, and he replied with the sweetest sound I have heard on my trip so far. “I know this man”. He walked away and made a call, probably to check my story out. I talked to J and it turns out that he had reversed the last two digits of his number, and his building had a new name that nobody knew about. He said he would meet me back there in 45 minutes.

So with this sorted out, I got dropped off at the right address and and sat by his pool sharing a beer with the security guard as I waited for him to come home. My ‘balls out’ were thawed with the huge relief, and I began to wonder how that horseshoe actually got in there.

J arrived with a friend and greeted me like family. A super nice guy, very personable, and incredibly helpful. He gave his buddy some money and sent him out to get groceries to make us a late dinner after I told him about my horrid day and lack of food. As I filled him in on the situation, he stopped me and said, “Dreams resort?” laughing, he told me that he in fact used to work there. And right then and there, he devised a plan for me to get in. He went as far as calling the resort to get room numbers of guests, arranging my transportation there, showing me exactly where to go with maps and giving me solid contacts that would help me from the inside if there were any problems. He even gave me his spare keys in case I had to get back to his apartment while he was at work. We chatted for a while and I crashed out hard and fast after this most difficult, bizarre, and trying day of travel, and did so with great relief, optimism, and not even the slightest discomfort from the even more evident horseshoe I was lying on.

With a game plan set, I hopped on my arranged ride and he took me to a military beach posting which had access to the harbor and beach. A narrow 10 ft. Break in a fence with armed guards protecting the so called public beach and harbor. So I began strolling down the beach as casually as possible, trying to blend in with the binge tanning, Pina Colada drinking vacationers. Thousands of people were scattered everywhere, resorts were hard to distinguish from one another and security prowled along the water. Out of the crowd, a familiar and surprised face jumped out to greet me and help make the transition from backpacker to vacationer. He brought me over to some other friends and we all shared an awkward, try not to over react, you actually made it? greeting. I noticed some nervous faces as a man from the resort approached with one question on his mind. “Something to drink mon?” And like that I was in. I did my best to blend in, and took full advantage of all the amenities, food, beverage and good times I could handle, knowing it could all be taken away at any moment with unknown repercussions to follow. With $6 to my name, I did it. I made it to the resort and wedding I said I would not miss. It was a grand reunion of many friends of over 20 years and many new friends met along the way, all there to celebrate the happily ever after of two wonderful people. And celebrate we did, as only this crew can.

Far from home safe, I was constantly reminded that I had $6 to my name. Getting back to Santo Domingo by the cheapest possible bus would costs $9. There were many offers to take some cash from my friends but that was not an option as far as I was concerned, defeating the purpose of my challenge which I was getting more and more excited to actually pull off. At some point during the first night, I had a theory working in the back of my mind. $6 is clearly no good to me since I need $9 to get back for my flight, right?. So it was time to test the durability of this horseshoe I was traveling with and hit the casino. There was a $10 minimum for BlackJack but I managed to talk the pit boss into letting me bet 5 of the dollars burning a hole in my pocket. With a goal of $12, enough for one plate of rice and beans and my bus ride back, I handed my money over to the dealer of fate, and won my first hand. The problem was, $10 was not the $12 walk away amount I set. So I let my money ride. And ride it did, all the way down to the loneliest number of $1 to my name. On that note, I walked away and never thought of it again for the rest of the night. It wasn’t hard with so many distractions available to me, but it would come back sooner or later. The way I saw it, I was far from down and out, and if worse came to worse, I could always hitch hike back or rely on the kindness of strangers, playing a little tug of war with karma. I still had that dollar in my pocket, so the next night I found myself back in the same casino watching my friends playing Roulette. For one dollar, I was able to play the inside numbers of the table, but I needed an initial buy in of $5. So my friend put up the $4 and I spread the rest of my money over the board like I knew what I was doing and waited for the wheel to decide the outcome of the final leg of my adventure. As the ball bounced around from number to number, I pictured the next days obstacles running through my mind, and then it landed, ever so softly on my number. A hit? Are you kidding me? I could not help but laugh long and hard over the plain dumbass luck I just received. The horse may have kicked me in the ass before but he left his lucky shoe behind for yet another shot. The $4 went back to my friend, I pressed my luck with one more spin for $5, and cashed out for exactly $12, the goal that started this insanely small time casino run. I have won hundreds at casinos in the past, but this $12 was the sweetest, and most memorable payout I have ever had.

The next day was spent sitting poolside and hanging out with everyone before I was to set out on the journey back. The same ride arranged on the way in was to pick me up at the same gates, get me to my bus and pick up Jose’s borrowed house keys. I said my goodbyes very openly in the front lobby and slipped out along the beach as easily and unnoticed as I came in. I made the long walk down this beach for the second time, but this time it was with settled nerves, confidence, relief, and the biggest unshakeable smirk my skinny face could handle.

The route back was virtually problem free, and I got to the airport at about 10pm for my 6am flight back to San Jose, with 120 pesos to my name which was soon spent on a sandwich I was able to talk myself into getting for half price. I sat around reading and listening to music, still smirking, thinking my Dominican Republic experience was over. But there was one last moment of excitement. In the lounge area there were a few others spending the night. What started as conversation between my bench neighbors, soon erupted into heated yelling and arguing. I slid my book into my bag for an easy escape and decided to take in the show. Sure enough, the curtains went up and the show began momentarily. The woman sitting closest to me stood up, screaming at the top of her Spanish lungs and began getting in another groups face in ‘oh no you didn’t’ fashion. There was swearing, pointing, scolding…and then she got really angry. She began picking up big metal garbage cans and throwing them about like a drunken fratboy with an empty keg. Garbage spewed everywhere, and the loud metal cylinder echoed through the nearly empty airport as it knocked over line dividers and smashed against walls. The reaction of the entire audience was just pure, gut wrenching over the top laughter, foot stomping, and knee slapping…and it was hilarious. My only reaction was to laugh. It was as if I were at a live taping of Jerry Springer after a paternity test gone wrong. The only thing that shocked me about it, was how long it went on before security came to stop it. It had to have been at least 10 minutes of rampage in an international airport before the first personnel came on scene. It actually went on long enough to become boring, and I packed up and moved to a new and quieter location when the rest of the security approached, only to see the same woman the next morning boarding my flight.

And the last issue to deal with….the proof of my return ticket I was supposed to deal with before I left. I was able to contact a friend I knew traveling around the world and she was kind enough to send me her online itinerary. I simply cut and pasted it, removed her name, and made the list of 6 flights very small and hard to read. With nothing more than a quick glance upon re entry, I was stamped and allowed back in Costa Rica. Smirk still on face.

This seemed like the perfect ending to this adventure and summed up the entire trip with a simple shake of the head. I put myself through a lot, as I usually do, and for what reason? I could have spent more than the lacking budget I gave myself, but I guarantee I would not be walking away with the same experience I got out of it. I admit I got extremely lucky in a few cases. So much so that I can’t explain it. Forces at work? Karma? Whatever. But I will knock on wood and say that I chased a unique experience and without a doubt, caught a big one. This so called vacation from my vacation with such high aspirations of rest and relaxation, quickly turned to trial and tribulation. But I pulled through, accomplished what I set out to do, had a hell of a time, and I would not have changed a thing about it.



prince says February 6, 2011,9:00 am

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Absolutely incredible buddy, I had no doubt but extremely impressed nonetheless. Let the horseshoe ride on.



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I am a 29 year old Canadian who has been traveling and chasing experiences over the last as long as I can remember with no plan or ultimate destination. My thirst for adventure has...