Airfare and Air Passes
When first planning to backpack, EVERYTHING needs to be, well...affordable! Airfare can get expensive, therefore every backpacker's question is: when is the best time to purchase airfare? Not only is airfare important but everything that comes with taking a flight needs to be inexpensive, for example, those annoying baggage fees.
Whenever I travel I try everything I possibly can to avoid paying for checking-in baggage. When I traveled to the Caribbean, I only took two flights: an American Airlines international flight into Haiti and Jetblue back to New York from Puerto Rico, without paying for baggage fees. If you are planning to backpack the Caribbean it would be ideal to travel with Jetblue because they do not charge baggage fees for both domestic and international flights. However, if Jetblue does not go to your desired destination then make su re to fly into an international island/country first such as Haiti or Dominican Republic because ALL international flights allows one free bag at check-in. Preferably, flight out of Puerto Rico with Jetblue. There are always ways to avoid extra fees, just get creative.
Best times and days to buy airfare:
Highest Fares: Because this is peak season, from mid-December to mid-April airfare are at its highest
Less Expensive Fares: During hurricane/rainy season, June, July and August, flights are less expensive
Lower Fares: Spring and Fall seasons, fares are at their lowest
Before travel became prominent in society, people mostly traveled to the Caribbean during winter, but now travel to the Caribbean is year-round. From my experience, traveling in the beginning or middle of the week, results in lower airfare. Traveling Thursday or Friday and sometimes even Saturday can be expensive because these are usually the days people travel. I usually search for flights and vacation packages through Booking Buddy, a site that compares all discount sites at once.
Airpasses
What many people are not familiar with are air passes. Air passes are for those who desire to island-hop and explore many regions in one trip.
Star Alliance - a website where you can plan your own itinerary throughout North America, choosing from 300 airports and 20 countries
One World - allows you to book up to 10 flights around North America, Central America and the Caribbean
No less than four years ago, many carriers such as American Airlines had Caribbean air pass programs that offered extremely affordable packages. Unfortunately, many air passes to the Caribbean are long gone. However, air passes to Asia, Latin America and Europe still exist and are quite popular. I will make sure to update any air pass information I come across. Until next time... Saludos!