For my job I work on a private yacht that is based out of Boston and the Caribbean. I spend my summers in New England and winters in the Caribbean usually St. Martin, Antigua and the USVI. It’s a fabulous way to get to travel and get paid to do it! I can’t think of a better job to have out of college! I live on the boat and food and living expenses are paid for so I don’t have many bills. I get to save a lot of money this way but I give up getting to have my own place! Essentially, it’s like living at home with my parents again!

It’s really cool that you’re planning an around the world trip! Where are you planning on going, for how long and are you going alone or with others? Western Europe can be quite expensive. I found the best way to find places to stay was to stay in hotels with a few friends instead of hostels. It’s cheaper and usually nicer. Hostels in Western Europe in my opinion are universally disgusting! But in South East Asia, Africa and South America they are not only cheap but often immaculate especially Asia. Something to keep in mind. If you stay in one place for more than two weeksEating out gets too expensive so I recommend shopping at grocery stores and fixing your own food. It also gives you the chance to check out grocery stores which can be a culture shock in itself! Think about going in on making a dinner with people at your hostel, it’s cheaper and you get to know the other travelers around you. They can tell you where they’ve been and what they recommend. I’ve found this the best way to find good places to stay. Lastly, talk to locals about what to do while you’re there. They’ll tell you of the best night spots and where you can find free “locals” only entertainment! Including the cheapest place to grab a pint.

As for flights, in Europe easy jets and ryan air can get you from country to country for as low as $20. There are tons of websites that can help you find cheap flights. Usually, if you can wait it out patiently until the day you plan to fly the flights get cheaper. Risky but can be worth it. Most countries as far as I know are pretty lenient on one way tickets. BUT!! It’s best to find out before you try to go. You could buy a one way ticket, check in at the counter and they won’t let you get into the country unless you have a ticket out or proof you are traveling by some other means (i.e. train, car, ferry). That could get expensive and blow your budget!! This probably could go for your brother too. He’ll need proof just in case to show that he plans on moving on and not staying in Japan. Although, Japanese are pretty nice to American tourists. I got entry for a year no questions asked so he’ll probably be fine. I could write you so much more but I’ll leave you with that to digest for now!. I hope this helps Let me know if you have more questions!
Happy travels!
Jerri

My name is Tim and I am so happy to see what your doing, I plan on traveling the world too! I’m 21 now and doing extensive preparations for my exciting journey around the world! I was in iTunes and looking up travel podcast and found yours. I’m from Texas too! I listened to your show and checked your site out and I did have some questions for ya. I noticed you talked about travel being linked with your job and thats one way all this travel was possible. What is your job and what is the best advice you can give me about low budget travel, do you only stay in Hostels, how do u get the lowest airfairs, and how do your airfairs work when you go from say one country to the next as far as return flights and exit flights. I know my brother is going to japan and they want him to show proof of a return flight, so what would he do if he planned on going to another country after japan, would he be required to by that ticket before entering into japan. I am just really curious on how you go about funding all your travels, did you have it all saved up, or do your work along the way or is your job in each country?

I would appreciate if you could help me out by answering some of those questions, it would be awesome! I will continue to read updates to your site and listen to you podcast!