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What skills do you have that you could use while traveling? Some employers have seasonal work that you may be able to train for or do easily. Research online and you will find travel-based jobs for every kind of skill. Adventure outfitters and summer camps recruit guides in the off season. If you want to be a rafting guide in the USA, start looking for summer work in the autumn or winter.  Surf instructors in Costa Rica work during the winters. Make a travel plan and network with other guides who can provide job information. Resorts need staff for every activity they offer, so find out things you can do at your skill level. Traveling nurses are in high demand. Many agencies will hire nurses from three months to a year to work at hospitals around the USA. Some even offer housing. Search online for traveling nursing positions and contact the recruiters. Most websites list location, pay rate, and benefits up front. Airline pilots, flight attendants, cruise ship staff, and transportation employees such as truck drivers travel as part of their work. While some of these jobs don't allow for much time to explore tourist areas, travel professionals can find ways to get out and enjoy, too. Research the industry to see what kind of skills and training are required. There are many opportunities to teach English abroad. Most places require that you take their Test of English as a Foreign Language (TOEFL) training class before you can sign on. This may expensive, but once you have the TOEFL certification, you can teach in many countries. Agencies often help with job placement. Many tourist destinations have resorts, theme parks, and restaurants looking for waiters, housekeepers, and attendants. The highest seasons for family tourist destinations are when children are not in school. For other places, high season may be during the best weather or centered around holidays. Check around for vacation high season in the area where you want to travel.
Get a travel industry job. Become an adventure guide. Get a job as a nurse. Become a travel professional. Try teaching English abroad. Get a service industry job.