If you are well prepared and still afraid then you need to push through that.  While talking to many people about traveling I get the same questions over and over again.  "Aren't you afraid of getting hurt?  Aren't you afraid of being robbed?  Aren't  you afraid of being attacked by snakes?  Aren't you afraid of getting into an accident?"  They heard that there is a lot of kidnappings in Colombia.  They heard that there is a lot of violence in El Salvador.   It's the same questions over and over again.  When I first started traveling I was afraid.  I was afraid of everything.  My first time to Costa Rica I was afraid of getting onto a bus with local people.  Thinking back to it now it's kind of funny.   Seeing this big tall white dude with a woman's spring jacket getting onto a bus with his back up.  He's ready for anything.  The more experience that you have in uncomfortable situations the less that they will feel uncomfortable.  Embrace feeling uneasy.  It sharpens your senses and makes you feel a rush.  It's like a drug.

You obviously still need to use common sense in every situation.  You aren't going to go downtown Medellin, Colombia on your own at 1am.  Would you go to downtown Harlem at 1am?  I know that's a bit of an extreme comparison, but it's just as stupid.  Sometimes some of the simplest and cheapest things that I have done have been the most rewarding.  Climbing a mountain in Nicaragua, traveling five days to the lost city in Colombia, and hiking Corcovado in Costa Rica especially stand out.  Seeing a Tapir out in the wild.  Being able to approach it and actually pet it.  Probably not the smartest move that I have made.  It worked out.  When we were in Venezuela an anteater came into the village we were staying at and just wandered around looking for ants.  It was the coolest thing.  Things like this I remember. Having a margarita on the random beach that I was at three months ago.  Not so much.  Some people will always be resort people, but they will never know that they aren't until they try something else.

It takes some time to come out of your comfort zone.  People always want to do what they are good at over and over again.  My specialty was sitting on a beach and drinking beers.  I am still really good at that.  I still really enjoy it the odd time.  If you would have known me when I was younger you would never would have thought I would grow up to be this person.  Terrified of everything.  Just wanting to stay sheltered.  It's not just with travel.  It's also with food.  I thought people were crazy that were eating curry.  Sara would want to stop there after a night in the hometown.  Now I crave curry.  Just stepping outside of my own bubble is comforting.  Knowing that I can travel to almost anywhere and be able to manage is a nice feeling.

If I could offer any type of advice.  If you are looking to step outside of the everyday travels of Cuba, Dominican, and Jamaica.  Start with something fairly close by.  Costa Rica, Nicaragua, Colombia, Panama, and El Salvador.  Stay at hostels.  Check reviews online.  Hostels are wonderful for helping travelers.  Always have things on the go within the area that you are in.  Take local transit.  Eat at local restaurants.  Don't drink powdered milk.  Seriously though, there is very little danger in nearly every one of the country's that I have ever visited.  I am not going to the jungles of the Congo anytime soon.  There are so many things to see and a short time to see it all.  You can still fit in that beach time if you want next year.  This year do something a little more memorable.

Some people don't have this built in them.  At least go and find out if you do.  Don't think about what could have been.  I am a case study of a person that had no idea that he would love travel so much.  I am just speaking from my own experience.  You never know what you are going to be into until you try it out.  I know I talk a lot of smack about resorts.  Well it's because resorts suck.