Europe or America?

Cuba can be inexpenisve if you stay in homestays. If you can find someone to share the room with all the better as most are priced per room and not per person.

Nicaragua and Guatemala are also inexpensive. You can get a shared room in a hostel for about $10, private rooms can be found for under $20 and food is cheap. There is lots to see and do in both countries. Costa Rica is one of the more expensive countries in Central America. Most of what you can find in Costa Rica can be found in Nicaragua but with a far less structured tourist infrastructure.

Look for places to stay that have shared kitchen facilities (or at least a fridge in your room) and you can save a lot on meals by making your own. I bring a steripen which is a UV light water purifier so I don't need to buy bottled water. In just over a minute I can drink the tap water.

Get a good guidebook for the areas you decide to go to. Look on this forum and others such as trip advisor for other people's experiences. There are a travel blogs out there by budget travellers who managed Central America on $30/day.

One option for covering a lot of ground is to join up with a budget tour for some of the time. There are some out there for Central America and Cuba for under $100/day. The advantage of that is often they will assign you a roommate, look after all the transportation and lodging but allow you to do what you want at each destination. You also get a travel guide who knows about the area you are at so you don't waste time and money on things that don't interest you or go on expensive side trips when there may be a less expensive option out there. Tours only will be of use if they go where you want to go.

The United States is a big place and expensive to get around. If you have a means of transportation (able to rent a car), you can camp in national and state parks for a reasonable price. However, you would need to pick what area you want to see as you can't manage the whole country in one trip. The other means of ground transportation is by bus. The intercity buses often drop you off at the edge of the city or in an industrial area so you are on your own to get around. Most of the cities have good transit systems (bus and/or subway/train) but a lot of small towns have nothing other than taxis.

In Peru, if you wanted to hike the Inca Trail to Machu Pichu you need to buy the tickets long in advance as they sell out quickly depending on the season. You have to go with a licensed tour company. That 4 days alone will cost a minimum of $500. The other hikes in the area don't need to be booked as far ahead.

Have fun on your trip. Regardless of where you end up you will have a memorable time.

Kayak05, thanks for all the tips and the nice words.
I don't think I'll take a tour, but I'll search and have a look anyway...

And, btw...does anyone know if there are other cheaper ways to go from Dallas or Los Angeles (Whichever is cheaper) to Cancun? The flights are around US$200. Bus?
I can also fly in to Brazil and then go up, but I imagine that would be a lot more expensive?

You can fly nonstop Dallas-Cancun for $111 with Spirit on a good day (add luggage fees though! unlike other airlines, they charge even for carry-on). LA-Cancun for $200 sounds reasonable.

You can bus it all the way down, but I doubt it'd end up cheaper.... Although if you book in advance you can make it to Mexico for like $2 with Greyhound :) I did that last year from Nuevo Laredo (Mexico) to Dallas.

Going overland would allow you to visit some other places on the way if that's of interest (Austin, San Antonio, Monterrey, Veracruz, etc).

I would double and triple check about the US visa giving you access to Mexico. That sounds very odd to me, but then they may have some kind of bilateral deal.

Also when Kayak05 suggests that you need to take a tour for the Inca Trail. It's not so much a suggestion as a statement. The days when you could just do the Inca Trail by yourself are long gone (almost 10 years now I believe). So if you want to do the Inca Trail you'll have to book yourself on a tour - and do it early as permits run out fast.

If you take a bus into Mexico, you'd better wear kevlar skivvies. Take a cheap flight.

It may be difficult... to re-enter the U.S.
We're going through some weird stuff right now.

If you take a bus into Mexico, you'd better wear kevlar skivvies.

Nah, that's an exaggeration. That particular border crossing (Laredo/Nuevo Laredo) I entered around midnight. I've also entered at other borders many many times; Cd. Juarez, Mexicali, Tecate, Tijuana. Never experienced or seen anything bad (except a small extortion in Tijuana, but no shootings, and actually one robbery at gunpoint in Cuernavaca but that was not at the border, oh, and I was robbed by four police officers in Acapulco I guess but again no shootings and at night and far from the border). Anyway, the general consensus (from people who know) is that as long as you enter during daytime hours and don't trade dr[u|]gs, you'll be fine.

It may be difficult... to re-enter the U.S. We're going through some weird stuff right now.

?? what do you mean and why?

Hey, guys...

It has been a long time. But finally the time has come for me to look around for tickets.
Anyway, in the end I have decided to go into Cuba first in my journey before planning and then travelling in Central America.

So, here I am again to ask you guys yet another question:
Recently (After pondering Jakarta-Osaka-Havana which will be around $2200, and Jakarta-Havana for $2700. This all, btw...is just what the tickets says. In reality, all of these flights have transits either in Amsterdam or USA) I am left wondering if there are better and cheaper ways for me to reach Havana.

Are there any USA port that is popular for reaching Havana? Thus I can get cheaper price? Or a direct to Cuba from any USA port is just too expensive? Is going through Yucatan/Cancun really is the best way?
Jakarta-Chicago is $1800 btw...and I am using this as a rough estimation for Indonesia-USA flights. I am looking forward to someone proving me wrong, though. In a good way.

I have mentioned LA and Chicago in my old posts. But circumstances has changed, and now I am faced with infinite choices of USA Airports to choose from. :) That, or I go through Japan...if nothing is cheaper.

Again, I am hoping you guys would come to my rescue and give me some more valuable insights. I am looking forward to it, and as always...it is most appreciated.
Oh, and I would also very much like a recommendation for flight booking sites.

Thanks anyway.

REAGEN

P.S: All the above are round trip prices. I just want to know how crazy things can get, and maybe prepare for it!

Check skyscanner and kayak.

yes. those two let you handicap 3 days b4 or after target leave home date.

first flight in the morning is chaepest. Usually Tuesdy. Nobody wants to pannic rush to airport. :)

Which exactly are the countries you are planning to go to now? Why are you looking for return tickets to Cuba if you plan to go to all these other countries? And when and for how long are you planning to go?

Why is Jakarta-Osaka-Havana $2200 when Jakarta-Havana is $2700? Is this if you buy flights separately? You need to be a little bit more detailed for us to hep you.

You won't be able to fly from the US direct to Cuba, I think. Cheapest way I know is from Mexico. I know some airlines fly fairly cheaply from Europe, like Condor, you might want to look into that. But in that case, I guess you'd want a one-way to Cuba and then fly on to Mexico or something, right? That makes things a bit more complicated.

From Jakarta, if you want to get to North America, look into flying to Los Angeles or San Francisco. Look into catching a cheap Air Asia or something to Singapore or Kuala Lumpur and flying from there instead.

If you are planning to travel during summer (Jun-Aug), note that tickets tend to be more expensive. If you are planning to travel during spring like you said initially, well spring is now, so that might mean you're looking at last minute tickets which also tend to be more expensive.