There are many different kinds of people who go on trips. There are businesspeople flying from one city to another for short meetings, families with young children taking a two-week trip to the sun, and students or people on gap years who will be backpacking around exotic places on very small budgets. There are almost as many different kinds of travellers as there are kinds of people.
There are many ways to book travel plans. Your main concern may be convenience. For example, if you have a meeting near the airport, you may only need a place to stay near the airport and nothing else. If you are travelling for fun, however, you are likely to have fewer restrictions and be open to all kinds of arrangements. You can have a travel agent set these up for you, or you can do it yourself online. Or, you could just go to a city or country with no plans and see what happens when you get there.
Health and travel insurance is something you should always have with you when you travel. Obviously, your needs will change again based on the type of travel you are doing. If you are travelling for business, it is important to have full travel insurance that will let you take another flight if yours is cancelled or runs late. This may not be as important for most people on vacation. If you're travelling with kids, you might want to think about it, but if you're not, you might be able to be flexible and patient if there are delays. But you might be more worried about your luggage and other things and want to make sure you're covered well in case you lose or damage them. There are many travel insurance companies on the market today, and they all offer all of these options.
In general, when you travel, you will always need health insurance. You can't afford to take the chance of getting hurt badly or in an accident if you don't have the right insurance. In many places around the world, national health insurance is not free, and if you need medical care, you will only get it if you can pay for it. Especially if you're travelling with kids, you should always make sure you have good travel insurance that covers medical costs. This is just a risk you don't want to take on your own, especially since travel insurance costs so little.