Cheap Flights to Dominican Republic

I was on a look out for cheap flights to the Dominican Republic and was hoping to score a reasonably priced deal, similar to that I scored in January. Unfortunately, planning to travel in August is not the same as going in January. It reminded me of December – it’s near impossible to score a cheap plane ticket in December because many people travel during pre Christmas season and for New Year making it one of the worst month for travel deal hunters, but come January, prices drop instantly and significantly. Take Dominican Republic for instance – I wanted to go on a trip during Christmas/New Year season of 2008 but was discouraged by outrageously priced flights so I wasted 8 consecutive days off sitting at home watching TV. But then when January came and I saw the same ticket that sold out planes for $850 + taxes in December now priced at $48 + taxes, I did not hesitate and went right for it. After all, there’s little difference in weather between the end of December and beginning of January and getting the ticket for less than 1/10th of the price it cost two weeks ago was a no brainer.

It was similar with August, though. I started looking for cheap flights to the Dominican Republic in July for the departure at the end of August. But having previously gone to the country for $48 + taxes, I was finding it hard to pay $600 + taxes for the same ticket. I have quickly realized that many people travel in Summer so prices are jacked up so carriers can milk as much as possible out of Summer eager people. This was making my plans to depart at the end of August difficult. I could not bring myself to pay twelve times more than I had paid seven months ago. It just messes with your brain when you realize that.

Having had vast experience scoring the best priced flight tickets from my previous travels, I knew that booking engines of most travel agents use the same backend. Being a computer developer myself, I could see that 80% of all travel agents in Canada use SoftVoyage as their booking engine so no matter which website of which provider you go to, you will get the same results which are priced in the same, or very similar way. That’s a great thing to know as it will save you heaps of time you would otherwise waste browsing through countless websites, yet getting the same results. The websites that use SoftVoyage travel booking engine include:

  • iTravel2000.com
  • RedTag.ca
  • ExitNow.ca
  • SellOffVacations.com
  • FlightCentre.ca
  • etc.

One travel agency that doesn’t use SoftVoyage is Geo.ca which is worth checking out because results will be different, though from what I have noticed, it’s mostly more expensive. Other than the travel agencies, I also kept a close eye on flight carriers themselves. The following were a must:

  • WestJet.ca
  • AirCanada.com
  • United.ca – great, but not for flights to the Caribbean
  • SunWing.com – amazing for Caribbean destinations, often very cheap, but only works well if you live in Toronto or Montreal. Edmonton didn’t have very good departures and prices

No matter where I went, the prices were nowhere close to anything I would consider decent. August simply proved to be a tough time of year to travel on the cheap. Then there was also an issue of timing – I wanted to depart at the end of the month to use up the money I have already spent on rent and to not have to spend more by overstaying for any part of September. That was also complicating things a bit because flights to the Dominican republic departing in the middle of August or middle of September were cheaper than flights departing at the end of August, beginning of September. My initial research did not encourage me at all. Maybe had I not gone to the Dominican Republic for $48 + taxes before, I would probably find $600 + taxes normal, but after flying cheap, I found it really hard accepting the price that was so much more expensive but would give me exactly the same thing. It was discouraging, but I kept working on it.

Best Country to Start the Around-The-World Travel In

I had the best time to start travelling worked out, now I just needed to work out where to go to start my around the world travels and to find the most affordable way to get there from Canada. Because I didn’t have much budget due to rather low positive cash flow at the time, I figured that the best country to start my round the world travel in would be one of those I am familiar with, one I have recently visited. If you go to a whole new country for the first time, you are rather overwhelmed by its culture, its people, its way of life and if that is a third world country, you will be harassed by touts since you first step foot on their soil so falling for overpriced deals is easy. However if you go to a country you have previously visited, you will know where you are going, what you are doing, what’s around the corner, where the best place to get a ride is, whom to talk to to get cheap accommodation, etc. Many of these can be chosen wrongly if you are in an unfamiliar place because you are under time stress and with a backpack on your back – you often have to take what comes your way and touts are very skilled at getting the most out of each tourist.

Based on the above, I basically only had two countries to choose from: Cuba and the Dominican Republic. I have also recently visited Iceland but not only Iceland is not a third world country (far from it), it is also one of the most expensive countries in the world so my budget would not handle it. I’d love to revisit Iceland as it’s by far the best country to travel to, but it wasn’t an option at this time. Plus because of budget issues, I had to keep it within close range because the further you travel, the more expensive the plane ticket and since Caribbean countries are popular tropical locations for many Canadians, flights there are frequent and far less expensive than flights to Europe or Asia. So in order to keep the initial cost low, Caribbean would be the best choice.

Out of other two countries I have recently visited, Cuba was the least favorable option. Their economy is too dependent on tourism so prices for accommodation are regulated by the government and locals are not allowed to offer foreigners any services for which a foreigner would normally have to pay. For example even if I had a good Cuban friend, I would not be able to crash at his place for if Cuban police found out, he’d get in serious trouble. Same goes for offering foreigners a lift or any other service. If you are a foreigner, you should only be seen riding in taxis or buses. If you are seen in a regular car, the owner/driver of that car could get in a lot of trouble for offering a tourist services for which that tourist should pay. That’s the way it works in Cuba which makes it one of the most expensive countries in the Caribbean (unless you decide to go illegal on everything and risk getting kicked out, but then you can be there on so cheap that even India is more expensive).

I’m not much of an illegal guy. I couldn’t even jump over the fence to join a festival in my home town when all my buddies went that way. I could jump it, I wasn’t lacking there, I just could not bear the thought of doing something that’s not right. That’s just the way I am. Cuba would otherwise be an amazing option as it can be done on the cheap and it’s a safe and beautiful country. But right now it looked like that’s not the best place to start. I didn’t have the budget to retain legal accommodation, even if I stuck with Casas Particulares, which are significantly less expensive than hotels and offer more authentic experience. They are still charged on per day basis so monthly it works out more than you would pay for rent in Canada. I had to ditch Cuba for this very reason.

Whether I liked it or not, I was left with only one option – Dominican Republic. I didn’t mind that as after visiting the country in January, only a few months prior I really enjoyed my stay there and had wonderful time. Unlike in Cuba, unless you have high expectation and desire comfortable lifestyle, you can live in the Dominican Republic on very cheap. I was familiar with the country and the way it operates so ripping me off by offering me overpriced deals would be difficult. I could definitely survive there even though my monthly budget was low and since weather is warm year round and internet connections are decent, I’d be able to both enjoy myself and get some work done on my websites to boost my positive cash flow. Seemed like I have found the best country to start the around the world travel in and even though I did not ditch all other options, I kept all of my senses firmly focused on this nation. Now it was only a question of scoring the plane ticket and making other arrangements for a price I would be comfortable paying.

Early Retirement Planning

It was early Summer of 2009. Weather in Alberta has vastly improved which was great. Winter was long and tough this year – temperatures did not go above -30 Degrees Celsius for two months. Having summer with lots of sunshine and steaming temperatures felt uplifting. Meantimely, my mind was on a rollercoaster. Resumption of travel after many years of having been nowhere brought breath of fresh air to my thinking. My body was back in Canada from Iceland, but my mind was still on the road. Within a span of last few months I travelled to Cuba, the Dominican Republic, Iceland, Toronto and the Rocky Mountains. I loved it to bits and continued travelling in my mind. My time off work was spent on the computer, discovering places I would like to visit next.

I wanted to travel more. I needed to travel more. And now that the value of time and the idea of early retirement became well defined in my mind, I started to plan my exit from work and entrance into the world of travel. The way I saw it was that I needed to come with a strategy to quit work as soon as possible while causing as little uproar and talk as achievable. At the same time, I was gonna dedicate maximum of my off work time to the growth of my websites that bring the most revenue while entertaining offers for sale of websites that were more popular, but brought little revenue. I needed more positive cash flow which could be done by focusing on 20% of my revenue generators that generate 80% of my revenue and eliminating the costs associated with ownership of low income generators. And among all the essentials, I needed to find time to figure out where to go to start my tour around the world while keeping the cost of travel as low as possible.

Traveling frugally is not difficult at all. Average person could spend thousands of dollars for a vacation, but smart traveller will find a way to spend one quarter of that but will get four times as much. I laugh at people who pay retail prices for plane tickets, hotel reservations or car rentals. They are voluntarily ripping themselves off. It doesn’t take much. Scoring awesome travel deals is really easy, but I will elaborate on it in more detail later.

Planning my early retirement was fun. I had a lot to take care of, but it was fun. It was as if I had a giant catalogue of the universe before me and my job was to pick what adventure I’m going to have next. This was the feeling of freedom. I was in charge of my life giving everybody else no chance at controlling it. No one had any say at what I should do tomorrow. It was me who decided what I was going to do and I did strictly what was in accord with my plans. The world of adventure lied right before me. I just needed to polish up a few tiny matters and then… the journey itself.

Traveling as Means of Spiritual Awakening

The path to my early retirement and the spiritual awakening were waiting to happen. It started with my trip to Cuba in December of 2008. Visiting Cuba was my dream for as long as I can remember. Most of all, I really wanted to visit Cuba before it changes. I knew that US presidential elections that were about to conclude in fall of 2008 would bring the imminent change way too close. For many years I have suppressed my deep desire to travel but when US elections were around the corner, I realized it was a now or never situation. Time was against me, Cuba could change any day and if I were to experience it before big change, I had to act. The goal was to go before elections take place, which I never accomplished, however I still had at least a few extra months as even after winning elections in November, new US president would not be taking over the Oval Office until 2009. And even then, there were way too many seriously pressing issues which needed attention of new president so likelihood of a ban lift on travel to Cuba taking place this early was small. I still didn’t want to put the trip off any more than necessary and flew to Cuba at the beginning of December. It was amazing.

I only spent one week in Cuba, but it was my first trip after 7 years. I felt happy and uplifted like I haven’t in years upon years. I have forgotten how it feels to have an exciting day, to make whole day an adventure, to explore, to experience, to live. This had such powerful impact on me that come mid January 2009, I left for a weeklong trip to the Dominican Republic. This was even more extraordinary as I was in the traveling mood already so I made each day of my stay there richer with adventure.

These two trips within less than 2 months got me hooked on travel again. I still lived my corporate lifestyle, but took every opportunity I had to go to new places. Living in Alberta, Canada, I went for a brief two day trip to Jasper in the Canadian Rocky Mountains and started making arrangements for a big trip to a country I wished to visit my whole life – Iceland.

I left for Iceland at the beginning of June of 2009 and combined my trip with a one day stay in Toronto, Ontario where I have never been before. It was an amazing day as Kensington Market opened for the season that day so the area lived with many people, street performers, dancers, musicians, free hugs and everything else that makes you feel… awesome.

I spent amazing 10 days in Iceland and was blown away by sheer beauty of that country. It was 10 days of nonstop adventure and major spiritual uplift. The people I’ve met, the places I’ve seen, the things I’ve done – these were the best days of my life since… university. That’s right. It started coming to me that within last year I have done a lot of traveling and I haven’t felt that great for years. While I was traveling, I felt alive and happy.

I traveled to the Rocky Mountains two more times, this time making each trip last at least 3 days. I drove down the scenic highways across the mountains from Jasper to Banff the first time, making stops along the way and doing a lot of hiking to spend two awesome days in Banff afterwards. On my last trip to the Rockies I went all the way to Roger’s Pass in Canadian British Columbia where scenery is so eye popping I had my breath taken away nonstop. Again – I’ve done a lot of hiking and enjoyed every minute of it.

While trips to the Rocky Mountains were not trips abroad for me – being a Canadian – those were still trips during which I explored and had an adventure and it made me feel alive. So within less than a year – from December 2008 till July 2009 I have traveled to three foreign countries (Cuba, Dominican Republic and Iceland) and took three more local trips within my own country of Canada (Jasper National Park, Banff National Park and Roger’s Pass in Canadian Rocky Mountains). On top of that I have also visited Toronto which I truly loved and met some amazing people even though my stay was only brief. This travel reignited my dying Spark of Happiness which was nearly out due to corporate lifestyle I have succumbed to, but not entirely. Complete spiritual awakening after so much travel that re-ignited the spark was just a question of time and come July 2009, I was all there.