For some travellers those questions are irrelevant. You know why you are travelling because you are meeting a specific need. Whether it is for business or personal reasons, to attend a conference or your great-aunt's funeral, you know where you are going and what you intend to do. But for others, such as leisure travellers like myself, the question can be very important.
How detailed your planning should be will also vary. For some trips you don't need to plan at all. If you are heading off for the umpteenth time to see a regular customer or a relative you are fond of, you may not need to do more than throw some toiletries and spare undies in your briefcase, buy the tickets and call a cab to the station or the airport. If you are going to stay a week in a city you have never visited you probably need to do a little more planning and packing, but not a lot. Possibly all you would need to do is some reading on the city and its sights and culture, then choose a suitable location and accommodation. After that, buy the tickets, pack, call the cab and you are on your way.
But I tend to go on trips a little more complex than that. When I started planning my first 'round-the-world trip in 2002 my goal was very basic. I thought at that time that I had one single chance to see the world and I was going to see as much as I could for as long as I could afford. Consequently in 2003 we spent a month in the USA, visiting fourteen states by air and car, a few days in the Caribbean and four months seeing most of Western Europe and the British Isles.
We had a wonderful time, despite cramming such an enormous range of territory, languages, cultures and currencies into a short five months. I rarely felt rushed, threatened or stressed. I believe the detailed planning I did made the difference between enjoyment and disaster. I took over a year to make the plans and learned a lot by trial and error. I discovered something that surprised me along the way. I enjoyed the planning process almost as much as the trip.
I surprised the doctors and found I was still around after that trip so I decided to keep travelling until I couldn't. And I'm still travelling, nine years later.
The trips since then have been a little shorter. We went 'round-the-world again in 2006 for three months. Unfortunately, Australia is a long, long flight from anywhere in the Northern Hemisphere; we are simply too far from the rest of the world after my wife found that long plane trips were not good for her health. I went alone on the third 'round-the-world in 2008 and last year to South America; both were over seven weeks. In between those we travelled together on shorter flights to New Zealand, Fiji and New Caledonia for one or two weeks and regularly to Melbourne, Australia by road to see our family. We used that trip, 2000km each way, to see as much of South-Eastern Australia as we could by varying the route as much as possible each time.
Over that period I developed some basic techniques for the planning of my complex trips. Possibly some of them may help you plan yours.
The most basic of all questions, before you book anything at all, is where do you want to go and what do you want to see?
There are lots of factors you need to consider as part of those questions. If you are ready to head off to explore foreign lands, how foreign do you want them to be? Are you looking for a comfortable 5 star holiday in a culture not too different from your own, but in a pleasant and care-free climate? Or are you looking for exotic experiences, strange languages and interesting foods and don't mind a little discomfort along the way? Do you want to see old and historic ruins, ancient sites, beautiful countryside, or a modern vibrant metropolis? Or all of the above?
Work out those priorities first, because some of them may become mutually exclusive. Make sure you involve your partner. You don't want to discover your partner is only prepared to stay at the Hilton when you arrive at the youth hostel you pre-booked for a week, no matter how beautiful the view is or how delicious the breakfast may be.
I'll use myself as an example, but you must use your own interests and passions to decide which countries and cultures are the ones you want to visit.
Over time my focus on trips changed. The first one was based on “I want to see it all while I can”. Of course, it wasn't possible but we certainly saw a great deal; ancient and medieval, bucolic and modern. My next trip was more focussed on the cultures of Eastern Europe; I was particularly interested in the ways countries like Slovenia, Hungary, Slovakia, Poland and East Germany were recovering from the communist era. On my next two trips I made a conscious effort to see most of the great wonders of the ancient and natural world that I had not already seen, so I added Angkor Wat, the Taj Mahal, Petra, Ancient Egypt, Yucatan, Teotihuacan, the Nazca Lines, Lake Titicaca, Macchu Pichu, Colca Canyon, Galapagos Islands and Iguazu Falls to the wonders of Europe and North America that I had already seen. They became my “Wonders of the World” trips – but I also managed to include re-visits to some of my favourite places such as London, New York and Hawaii.
The trip I am planning at the moment is on a few levels. I love travelling by rail, so I have deliberately planned many long rail trips; some fast and modern, some more venerable. In one brief 14-day period I will take the Stansted Express to London, to catch the Eurostar to Paris, then after a few days the Lyria TGV high-speed train to Visp, connecting on a local to Zermatt, then the Glacier Express to Chur followed by the Bernina Express to Tirano. I change trains there for a local to Milan, then a local to Venice followed by the night train to Zagreb. Whew!!. And I'm going to love every minute of it. I won't be finished there because after flying to Dubrovnik I take the bus to Mostar and the train from there to Sarajevo.
I will have a second focus on this trip: food. I enjoyed eating local foods with the locals on many of my previous trips, especially in Mexico, Peru and Ecuador. I deliberately avoid the tourist restaurants when I can. I intend to do that as much as I can on this next trip, especially in Kerala, India and in Croatia and Bosnia and Herzegovina. On every trip I try to combine seeing new places, thus Kerala, the Balkans and Russia, with seeing old favourites and friends; in this case those are in the UK.
Do you have a passion? Art? Ancient cities and cultures? Medieval forts? Architecture? Foreign languages? Battles of WWII? Whatever your passion, consider basing a trip around that. That does not mean that is all you do or see on your trip, but it gives an additional interest and structure to your planning.
Once you have worked that part out, decide on the next two most important decisions. How long do you want to go for and what is your budget? Actually, the latter is probably the priority, because that may decide the time limit as well.