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how to plan a travel?

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Hello we are a couple from Denmark and Italy that are thinking to travel around in Asia from September and forward, but we have no idea how to plan the trip from the beginning to the end.

We need to know for example which order of the countries we want to go, a route..
and we need to know which injections we need for the trip and when to do them and if it´s better to do in Denmark , Italy, or in the country that we are going to.. (now we are in Denmark)
and then we dont know about the rules of visa in all the countries and how to get it.
how can you know how much money you need for the travel?

so we would like if someone could help us in all this confusion....

how do you organize a trip like that?

We would like to go in all the countries of Asia and there are also lots of islands everywhere (for example Philippines Islands, the Islands of Thailand and so on) and its almost impossible to know how much cost for go to all those islands and how much cost the food and living in all the countries and places.. and there are some activities that we would like to try during our trip then we dont know how much money extra we will need for this because there will be lots of things to do during the trip that we dont know from home so it´s impossible to know how much money to save up before to go.

we dont want to plan to much we want just to go there and explore it all with our backpacks and see the wild, the culture, live with the locals, eat the local food, and so on.. and we dont know for how long we are staying in each country and how long the total travel will be.. we would like also to try finding some work during the travel around but we dont know about the rules of working permission and so on.. we are thinking to use couchsurfing to find people to stay with in every place so we save money and live the life of the country.

we are thinking also to buy some backpacking gears like Tent, Sleeping Bag, Compass, Multi-tool, Flashlights, First Aid Kit, Water Filter, Pots/Pans, Tableware/Cutlery, Hiking Boots, Axe, Lantern, Knife, GPS, Solar Charger, Fishing Gear and so on..
like this:

so we can travel from country to country by foot to save more money and experience the nature and sleep over night for free..

so we want a travel with a lot of experiences, live like the locals, try as many crazy stuffs possible, see everywhere, see some of the important sightseeings... and most important CHEAP AS POSSIBLE..

any tips how to organize all this and tips to do it as cheap as possible?

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