I always get travel insurance when I travel internationally. It isn't just good to have if your trip gets cancelled, it's really helpful if you get delayed! If you have a layover somewhere and you miss your connecting flight due to the airline, your insurance kicks in. Covers meals and accommodations if necessary. Also covers you for lost/stolen/damaged baggage (not a huge amount of money but it helps). We actually had this issue when we went to Guatemala and it covered our hotel stay and meals! Totally worth the extra $28 for travel insurance IMHO. As for flights, why AirTran? Is it because of pricing? I just remember a few years ago when we had our family reunion in Panama, a lot of my family members booked flights with them and many of them had issues with delayed/lost luggage and also cancelled flights was an issue. This was actually during high season! No weather issues, they just sucked! It was the cheapest airline I think for a lot of people coming from all over the country. But man was I glad not to have used them. Maybe they have improved in the last 3 years? I don't know. All I know is I wish JetBlue was flying out of DC to Cayman!