Here’s how I’ve been planning my trip to Colombia (similar to how I plan any major trip):
Airfare - We settled on our (approximate) dates for travel and bought our plane tickets to/from the US/Colombia about four months in advance. I say approximate because we had flexibility of 1 or 2 days on either side. The best site I’ve used to look for airfare is http://matrix.itasoftware.com/ which is owned by Google.
Domestic Flights: I later used the ITA Software to also look up the domestic flights I wanted to take within Colombia, but found they didn’t use the same conversion rate as the actual airlines used. The difference wasn’t significant, but remember to check the final price when you buy the ticket.
Hotels - I mainly used Tripadvisor to check reviews and then Booking.com to make the reservations. I’ve used Agoda too, but for Colombia, Booking.com had the lowest rates (as shown on Tripadvisor). Also, Agoda doesn’t always send the confirmation voucher to your email, rather makes you sign into your account on their own site to pull it up. All the reservations were just that; they don’t charge your credit card right away.
Organization - Finally, I sent all the confirmation emails for flights and hotels to Tripit and they were automatically put into an itinerary for me. I will probably carry paper copies of these as well, but it’s nice to have the itinerary up on “the cloud” if necessary.
Insurance - If you’re spending a ton of money on travel, it’s probably a good idea to get some type of insurance. You can purchase this with your plane tickets, or a package on your own, or perhaps your credit card(s) offer some type of protection. I found out the life insurance I have with my employer also offers a special travel assistance program, so it’s good to check!
