Jerry and I have been on the road for only a month. However, we started planning our voyage 7 months ahead of time. Whether you think that 7 months is too long or not long enough, every second is necessary in order to make the proper preparations to leave. It is important to focus on one thing at a time and finish it. You do not want to start several preparations and leave them unfinished. The most important thing to do first is pick a destination and secure your accommodation there.
We spent weeks sending out house sitting requests and submitted our information to volunteer positions to Europe and North Africa through trustedhousesitters and helpx. Considering that it was a bit early, we were lucky to get accepted by our host in France. Once you find the perfect accommodation, you need to research how long you can stay legally in the country you will be traveling to. For Western Europe, or the Schengen Zone, Americans and most other non-EU citizens can only stay for 90 days for every 180 days. The 180 day timer starts the day your passport is stamped. You can come and go in the Schengen Zone as often as you would like, as long as you do not exceed 90 days total throughout all participating countries. This will give you a better understanding of the SchengenZone:
http://travel.state.gov/content/passports/english/go/schengen-fact-sheet.html
Next is saving money and selling all of your stuff! Very tedious but worth it. Ebay and craigslist are easy enough. Have a garage sale to get rid of the little things and get some extra cash. Take a moment to think about everything you spend money on and cut everything that is unnecessary. It can be painful but if you are passionate about saving money to travel, it is important. Just watch your bank account go up every week while you make other preparations. Make sure you use your bank to exchange foreign currency. It will save you money in the end because most banks do not charge more than the exchange rate. Also look into signing up for a travel rewards credit card. You can get free flights and accommodation for your various excursions during your new lifestyle.
Now you will need to find the cheapest flight you can find and shop for gear. Splurge on good shoes. Your feet and your back will thank you greatly for it. You will also need the perfect backpack for your trip. Research all types and sizes of backpacks. We use a High Sierra Titan 55. It is perfect for us, but you need to shop according to your needs. It will also pay off to buy a light tent. Many cities around the world have campgrounds just outside of the city, with transportation to and from the city center. It comes in handy during a nice summer day and is cheaper than other types of accommodation. You will also need a light, small laptop for keeping up with house sitting assignments and volunteer positions. Acer is not the best, but is an affordable brand that is perfect for the job.
The most difficult part for us was finding a happy home for our dogs. Remember, most of the time your pet cannot travel with you, unless you have enough money and patience to bring them with you everywhere. It is a sad thing to have to do, but you can always find a temporary foster so your pup is there when you get back, if you intend on coming back.
It is extremely important to research the country your are visiting, and get necessary vaccines for that country or any country near it that you might visit. Since we are going to Morocco, we needed a Hepatitis A and Typhoid vaccine. Many parts of Asia require a Yellow Fever vaccine. Some people choose not to get vaccines, which I do not recommend, but travel insurance is important too. My insurance already covers me for travel but you should find the right insurance for you in case you get your adventurous self into trouble.
This is just a basic outline of everything necessary for packing up and hitting the open road. There are many other important small things. I will write more detailed posts about the various steps listed in the future.
I forgot the most important step... find the courage to drop everything that is holding you back. Any reason you tell yourself you cannot do it, unless you have children, is a lie. I wish you luck on your preparations.
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