At the very least, you should ask yourself :-
WHAT am I trying to achieve? i.e. am I telling a story, capturing a moment, describing a place.
WHEN is the best time to achieve it? i.e. time of day, season
HOW am I going to photograph it? i.e, equipment, lighting and technique
WHERE is the best location? i.e. the best example of a subject or a suitable background.
Example:- For a vacation.
When is the best season to visit? e.g. in some countries you may specifically want to see or avoid the wet season or dry season, want to see autumn (fall) colours, have snow on the mountains. The season will affect your choice of clothing and also the type of vehicle you may hire. TIP: search weather sites or tourism sites online for the place you are visiting.
What subjects are there to photograph in the area? - look in guide books or online. When you get there look at postcards. TIP: Ask local people. They often know of local places not popular with tourists.
What time is sunrise or sunset? - you can find this out online before you go or even download an app for your phone. TIP: arrive well before sunrise/sunset and stay for a while afterwards. Good light is available before sunrise and after sunset.
What time does a local attraction open or close? - See online or get a guide book. Try to find out beforehand if you can use a tripod or need a photo permit. Some places do not permit interior photography! TIP: Get there well before opening time so you can get shots without hordes of tourists cluttering the shot.
Where is the best place to photograph something from? - Have a look at guide books and postcards before you go and get a local map to work out where the photos were taken from. Check for viewpoints on maps. TIP: Look at a map and check West or East of a location to get a sunrise of a sunset behind the subject, e.g. across a river or harbour.
Do I need any special lenses/equipment? - If you want to shoot a particular subject you might need a long lens or a macro lens or a wide angle lens.. Do you need a tripod or a monopod or would a simple beanbag suffice? TIP: Always bring a flashgun. It is useful in harsh sunlight for filling in shadows , for night shots and for dark gloomy interiors. Always remember your battery charger, without it you are dead in the water.
How much equipment can I carry? - NEVER put your camera, lenses and flashgun in cargo luggage on a plane, always include it as carry on luggage. Remember that you need to carry this equipment around all day, so get a jacket with plenty of packets, a safari/photographer's vest or a specialist camera bag that is comfortable to wear. TIP: I use a photographer's vest in which I carry a spare lens or two, spare SD cards, spare batteries, filters, cleaning cloths and brush and a bean bag.
Is my equipment insured? - Many domestic insurance policies do not cover photographic equipment taken abroad. Check you policy for this and also any other exclusions. You may need specialist photographic insurance.
Can I photograph people? - In many countries people do not want their photo taken or will ask for some money if you want to photograph them. Don't offend them by trying to take a candid photo and accept a refusal generously. Always ask a parent for permission to photograph a child. TIP: A smile will go a long way and always show the person their photo afterwards. Try to find out some of the customs of a country so that you do not offend people.
With a little planning and preparation, your photoshoot will go a lot smoother.