"Don't worry eat chicken curry!" as they say in Thailand. Actually if you hear a Thai saying this, you should worry, but this is a whole different story.
Here I'm gonna show you some stuff I use while traveling and how I travel. I want to show you how easy it is to get around, find places to stay and deal with all that comes to your mind, when you first plan your holiday trip or even a trip around the world for several month. There will always be a place to stay, a bus going somewhere, a plane flying somewhere or friendly locals helping you out. Find out how to travel cheap and still see a lot of the places you're going to.
There are several platforms where you can find cheap flights. There is always one rule: "Be an early-bird!". I usually book my flights at least half a year in advance. skyscanner.com & bravofly.com are by far my personal favorites. You can easily switch days of your booking and see how the prices are going up or down. Prevent flights on public holidays or weekends. Also make sure, which payment method you are about to use. Sometimes booking with Master Card is more expensive than booking with Visa. If you find a cheap flight, book it right away. The algorithm of those pages will remember your plans and prices will go up the more often you check it.
Since booking.com is the biggest platform for accommodations worldwide, it's obvious to use it for your travels. I use it a lot. Make sure to get some good deals by rating every places you stay and get into the genius program of booking.com. That can really safe you some money, especially if you are traveling for a long time. On my worldtrip where I stayed in over a hundred places I earned over 500 Euro just by rating hotels, hostels and apartments. For Asia I would recommend using agoda.com or hostelworld.com. If you're going to the US it might be the cheapest way to book a whole apartment on airbnb.com.
Actually there is not a lot of stuff in my bag. I love to go to Asia, so I mostly buy my shirts and short pants on some random markets. The prices are ridiculously cheap. I love my travel cubes. You don't have to search for stuff in your backpack forever and you can always separate fresh from dirty cloth very easy. I'm not a guy who's afraid to get robbed but I seriously don't want to get my passport, camera or laptop stolen. Therefor I use my pacsafe. I love this thing. Tie it up to a pipe in your hostel and enjoy your day at the beach without worrying about your belongings.
Imagine arriving in new city or a country far from home, nobodies understands your language and there if no WIFI anywhere near you. Well you could walk around and maybe find someone you can help you out or you download maps.me. It's working offline and I found my way no matter if I was in Africa, South America Oceania or anywhere in Europe. Just make sure you download the app and the region you are going to before arriving there. Not only that this app is showing you the fastest way, you can also find restaurants, bars, city sights and accommodations near you. There is no better travel app!
If you are on a trip for several month you might make sure to have two different credit cards with you. Some places do not accept all cards. When traveling outside of the European Union make sure to deactivate geo-control on your card to get cash anywhere in the world. I usually don't use additional insurances when traveling abroad. The "Master Card Gold" includes pretty much everything I need. Just buy something at the airport, when arriving at your destination and your insurance is activated for 3 month. If you want specific insurance you might want to check with some travel agencies near your home to find the perfect travel insurance for you and your adventure.
I always use an international drivers permits when going somewhere. Especially in Africa and Asia they will not let you go if you can't show at least a translated document. There are 3 different types of permits. Most of the countries stick to the oldest conventions but there are 2 new international ones. So take your time to really research the laws in the country you are going to. Also make sure to have your regular drivers license with you at any time.