How to go about

At first I would make a list of the places that I would like to visit and then I would look at the list and see if I could combine some of those places (if they are in the same part of the world). I would pick the country or the countries that that interest me the most and then I would check the price of the flights and the accomodation in those place and see if I could afford that. If it seems too expensive I would save that destination for another time and check the prices of one of the other places that I am interested in. Of course you can also do it in a different way and make a list and check the cheapest flights. If one of your places in on the list you could choose that destination. You also have to consider the visa requirements in the country that you want to visit. In some countries is complicated and expensive to get a visa and you have take that into consideration when you plan your trip. I am not sure about your last question because I don't usually book my flight and my accomodation together. I arrange my transportation first and when I have all the tickets I book my accomodation. On a site like Agoda you can find cheap accomodation but the site only lets you book certain types of rooms and not all of the rooms that are available at the hotel. On Agoda you pay when you book the room instead of paying when you check out of the hotel.

Ask yourself first what is most important to you. To be in a different place and see how you find your food over there since the other place/country and all it's experiences (which you can see all around you) are most important or the journey over there and being in an exclusive hotel etc. Personally I only want to be somewhere else so that will cost me the most. Sometimes I have a special country/place in mind, sometimes it just pops up. Next step I do is I search for more info, how I can live or what I need over there, what I would like to see, etc. I search for flights or all in travels (the last ones are mostly way cheaper esp. if I travel with my children). I always try to find the most cheapest option and that way I know what I need to save. If I set myself a goal (when I want to go) it's way easier to get the money. This besides of the fact I save a bit each month plus I put all the small coins aside (I use that money if I travel).

A package holiday booked fairly last minute can be cheap. It usually includes the flight and the accommodation. Sometimes it includes a transfer from the airport to the accommodation. The accommodation can be room only, bed and breakfast, half board or full board. To go to a different country you need a passport and money. I am an independent traveler and I usually book my flight first. Typically I visit a region and stay in five or so different places. I go to places listed on my travel wish list. It is a good idea to book accommodation in advance. The best way to plan is look at travel guide books and the Internet sites about countries you fancy visiting. First of all think about which are the countries close to your home country. Then find out flight, train or bus fares. Research accommodation costs after that. Good luck.