Looking at the school vacation calendar for 2019, we were excited to see a full 2 weeks off from school due to when the holidays fell. It was the beginning of spring and we had just gotten back from our epic trip to Dubai and were trying to figure out where to go to take advantage of all that time off.

We spent weeks brainstorming ideas. We kept coming back to the idea of going to Asia. Neither of us had ever been and we were thinking of Bangkok or maybe Hong Kong, or even Shanghai (or all three!). It’s a long way away, but with 2 weeks we’d have more time to adjust and enjoy.

Asian Adventure Planning

I spent endless hours looking at flights and itineraries, trying to get ideas on where to go and how to get there. A close high school and college friend of mine had lived in Thailand and Laos for 15 years so I leaned on him for ideas. I also tried to find ways of getting to that region on points and miles.

In the end, we were thinking of doing a whirlwind tour starting with about 5 days each in Hong Kong, Singapore, and Bangkok or some close approximation of that.

The only problem was that since it was Christmas, I wasn’t able to find a reasonable way of getting there. On points, the flights were either too expensive and/or they had killer layovers taking 36-48 hours to get to the destination or back. Those may have been okay with one or two of us, but certainly for a family of 4 flying in economy.

There were lots of paid flight options that could have worked, but they were definitely expensive. I think the best price I ever found was close to $2000 each way in the back of the plane. While it may not have been a horrible price considering the itinerary, it was hitting the wallet harder than we felt comfortable with.

Rethinking the Plan

By mid-summer, the Asian adventure idea had fallen out of favor so we tried to pivot. We decided to stay a little bit more local, which meant a trip to California. We had planned a trip to San Francisco last April but changed plans and went to Los Cabos instead. This seemed like a good opportunity to finally visit that destination. We didn’t want to spend 2 weeks in San Francisco so we looked for other places to go as well.

On a previous trip, we had gone to LA, Las Vegas, and San Diego. We really enjoyed San Diego and my wife had seen an article on the Ritz Carlton in Santa Barbara, which we could get on points. A plan was starting to form.

With 5ish days in San Francisco, we could fly to San Diego around Christmas and then spend New Years in Santa Barbara. We also considered flying in my wife’s brother for Christmas in San Diego as the boys would really enjoy spending time with him.

We had the basis for the plan, now it was time to solidify the dates!