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.