Last month I took my first trip to South America and it was amazing! The destination and particulars of this trip were actually picked based on the friend I was traveling with. She prefers Europe, I prefer Asia. Our site-seeing preferences varied as well. But we both valued eating really good food (we normed on what “good” is), drinking really good wine, and sitting around looking at beautiful mountains. And while we might want to do other things, if that’s all we did, we’d both be happy. So we picked Mendoza, Argentina and Santiago, Chile. We figured out we’d either need Avios or American Airline miles and since I had done the 100,000 BA credit card bonus and she had tons of Membership Reward points, we picked British Airways. When we were trying to book their award reservation system had that ongoing glitch. The agent was finding seats on the earlier flight, but showing no availability on the one I wanted. Even asking her to request the particular flight manually yielded no results. Other airlines were showing award seats available on that flight. So, I decided to wait a little while to see if they’d fix the glitch. Checked online multiple times over 2-3 weeks, same problem. Finally broke down and called again and got an amazing agent. He was upfront about the problems and willingly checked flight after flight from various departure cities to see if we could get my dates. Still no dice, but using 100,000 Avios miles to fly LAN business class seemed like it was a better value than using 135,000 AAdvantage miles for American Airline First. So I wound up booking tickets the same day, but on the earlier, daytime flight. To get from DC to Miami the night before we decided just to purchase the tickets on United rather than burning more miles. I thought a Thursday night flight to Miami would have a good chance of our upgrades clearing in advance but they didn’t, and when I went to check in I got a message for the first time asking if I wanted to split the reservation in order to be on the upgrade list. I decided a free drink and snack for a 2 hour flight wasn’t worth the headache in the off chance something happened to the flight and we were trying to coordinate two separate itineraries. (For more details on the flight, see my post on HeelsFirst) The recently opened Element by Westin hotel was our top pick for the overnight in Miami. It was close, it had a free airport shuttle, it was brand new, and only 4,000 starpoints a night! (Not to mention the Hilton had reports of bed bugs on Tripadvisor.) It only took us about 15 minutes to make it off the plane, determine there was no restaurant open in the airport and we’d have to get delivery, and get out to the hotel shuttle area. It took us another 30 to catch our shuttle. After about 20 minutes of watching every other hotel van pass by, including the Sheraton which came by at least 2 times, I called and was informed the shuttle ran every 20 min. Hmmm.