Throwback Trip: Pebble Beach 2014 – Flight Planning

I have had the American Airlines AAdvantage MasterCard since the early 2000’s when I was traveling frequently for work. At the time of this trip I had about 80,000 miles sitting in my account to use towards getting everyone out to the west coast.

It was only enough for 3 saver level tickets (25K miles each) so I would only need to pay cash or use my wife’s miles for one of the tickets.

In addition to being able to use the points, flying with American would also allow us to check our golf clubs for free and get priority boarding as those are perks of the credit card. This would save us $25 per person each way on the trip, or $200 total.

Searching

With the Pebble Beach hotel reservations nailed down I had to find award availability. We were looking for approximately a week long trip and wanted Pebble Beach to either be the beginning or the end of the trip. Searching for award availability as well as cash prices on the tickets, it was clear our best option was to fly into San Francisco rather than San Jose, an hour south. As for timing, the Pebble Beach trip was going to be at the end of the trip which made for a nice finale.

At the time there were no direct flights between Boston and San Francisco operated by American so we’d need to stop in either Dallas/Fort Worth or Chicago which are both hubs for American Airlines. Nonstop flights are almost always preferred when available, but we wanted to save as much cash as we could so we needed to use the miles we had available to us so we had to compromise.

Booking

After a few hours of searching and verifying availability with the rest of the group, we decided on an itinerary that left first thing on a Saturday and returned the following Saturday that flew into San Francisco with a layover in Dallas/Fort Worth.

I booked the award tickets for everyone else and in the process discovered my wife had enough US Airways points to get my ticket on miles rather than paying cash. US Airways and American Airlines had merged the previous year so the US Airways miles could be used for American Airlines award flights. While the flights wouldn’t be on the same itinerary, we wouldn’t have to pay cash for the flights.

The itinerary was for seven nights. We had 4 nights before our stay in Pebble Beach and one night after Pebble Beach. I needed to figure out how to split those days between the San Francisco area and the Pebble Beach/Monterrey area which was the next task on the list.