Note: From time to time I will highlight a significant trip we went on in the past as a “throwback trip”. The first of these trips is from 2014 to play golf at Pebble Beach. There will be a series of posts highlighting the planning aspects of the trip, daily diary posts detailing the actual trip, and a wrap up summary at the end. I hope you enjoy the posts as much as we enjoyed the trip!
Once in a lifetime… For the second time
While I don’t golf as regularly as I would like, I do play enough to understand the special draw of Pebble Beach. In 2004 I had treated my father to a 60th birthday present of a father-son trip to Pebble Beach. We had very high expectations going into that trip based on what we had seen on TV, what we had heard from people we knew that had gone, and everything we had read. Despite the high expectations that trip exceeded them in every way. It was a fantastic “once in a lifetime” trip we longed to turn into a “twice in a lifetime” trip. Funny how that works!
The more I travel I find there are often mental barriers preventing people, myself especially, from taking trips, going places, or doing things. These blocks affect us more than we realize. “I could never go there”. “That’s too far away/expensive/exotic/difficult”. Once we’ve done it once it becomes so much easier to turn that bucket list adventure into a repeat-but-better return trip. That’s definitely what happened for us with Pebble Beach.
For this trip we decided we wanted to expand the experience and invite my uncle and cousin to join us. They were part of our regular golfing group so they were natural candidates for our “dads golfing trip”.
This trip is one of the oldest trips I’ll document. Although it’s not the first time I used points to go on a trip, it is a milestone in that it’s the first time I used multiple types of points and miles for a trip and strategically applied for a credit card and signup bonus to help towards a trip. While I now know things I could have done differently to get marginally better deals, looking back I still did a pretty good job optimizing to meet our goals to minimize cash outlay. Most importantly the trip went flawlessly and we all had a fantastic and unforgettable time that still brings back fond memories and smiles to our faces. Isn’t that the ultimate goal of any trip.
Considerations
Pebble Beach is a special place for anyone who follows golf. Touring professions play there regularly as do celebrities and star athletes of all types. It’s also super expensive to stay and play there.
Given our budget we wanted to follow a strategy to minimize costs where we could to “save up” for the parts that were going to be expensive no matter what, which was basically our whole time actually at Pebble Beach. We’d use miles where we could, though at this time I was very much a rookie in the points and miles game. The focus would be on the golf and we’d economize elsewhere as it made sense without taking away from the trip.
While syncing up everyone’s schedules we found time the first few weeks of November that worked for all of us with some flexibility on the exact days. The goal was to go on a trip lasting about a week and we’d split our time between San Francisco and the Pebble Beach area and play a few rounds of golf other than Pebble Beach.
Up next up Pebble Beach hotel planning….
Tomatico Travels 
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