If your desire to travel out of the country is to experience other cultures, avoid the Caribbean. The Caribbean is beautiful, but in all likelihood you'll be at a beach resort with mostly Americans and Canadians.

Canada has some nice places (the Canadian Rockies are beautiful... Vancouver and Toronto are great big cities).... but its essentially an extension of the US, culturally.

If you want to experience other cultures, you've got to hit either Europe or Asia, IMO. Add South America if you are able to speak Spanish.

I've visited 20 countries in Europe, 6 countries in Asia, and 3 countries in South America, and I would say if you are wanting to travel outside the country for the very first time, you're best bet choice is either Great Britain or Italy..... you can add Spain if you are able to speak Spanish.

Great Britain has it all. London is such a world city that in some aspects it puts even New York to shame. But the British countryside has some beautiful spots with tons of history and quaint villages. But the best part is its a completely different culture yet no language barrier. That makes it a great choice to learn how to get around in Europe. Once you've mastered a city like London, it prepares you for a more difficult city like Paris.

Italy is also a great choice because the people are the most friendly in all of Europe. There is TONS of history. And because Italian food is so familiar, ordering in restaurants is very easy. You can venture to less touristy spots and still read the menu without too much trouble.

I'd avoid Paris until after you've mastered travelling Britain and Italy. Britain and Italy are the most accommodating to first time International travelers. France is a bit more difficult from a communication standpoint, but if you put forth just a little bit of effort, its not that bad. Still, it can be frustrating at times.

I would recommend travelling in Europe before you head to Asia. One of my favorite countries to visit is India... but its not for everyone. Most people I know who've visited India swear they'll never go back. It's crowded, loud, dirty, and heart-breakingly poor.... but it will give you a fresh perspective on how good you have it back home. Not to mention the food can be amazing. And you can stay in opulent hotels that offer luxury you likely wouldn't be able to afford in the US or Europe. China and other parts of East Asia are not nearly as shocking to Westerners unless you get out of the big cities.

I've not been to Australia, but similar to the United States, there simply isn't the history there that you'll find in Europe or even Asia. South America has a lot to see, but it too is relatively short on history.