We had figured out at the end of summer 2018 that we were headed to Dubai for February vacation, but we hadn’t settled on a destination for April vacation. April vacation is a little more constrained because the kids have soccer and other activities that can more easily conflict with going on vacation. For example we didn’t even know the dates we could travel because we didn’t have the soccer schedules yet. We were willing to miss practices during the week but didn’t want to miss any of the games which happen on the weekends.

Due to this we were focusing on shorter trips. Europe or beyond was going to be too far so we were looking for someplace closer. Not knowing the exact dates was also going to cause some headaches, but I went ahead looking at different itinerary proposals so I’d be ready once I got the dates.

San Francisco Here We Come!

On a trip to Hawaii in 2017, we had arranged an 8 hour layover in San Francisco. We used the opportunity to go into the city for lunch and walk around to see some things. The kids really enjoyed their quick visit and had asked about when we would be able to go back.

While I wasn’t ready to actually book flights, I searched and priced out itineraries using Google Flights to get an idea of what the prices would be like. I searched for hotels and even explored rental car options.

My basic itinerary was that we would fly in on either a Friday night or Saturday morning, spend a night or two nights in San Francisco to adjust. We’d then rent a car and drive to Napa and spend a day/night visiting landmarks there before driving back to the city to spend 5 nights on points somewhere in the city.

I had a free night certificate from my IHG Rewards Club credit card that was going to expire, so I preemptively booked a reservation at the Holiday Inn Express in Fisherman’s Wharf for the first Saturday night that I thought we might be in the city if my itinerary worked out. If I canceled it, I would lose the certificate (because it would have expired by then) but we weren’t likely going to use it otherwise anyways so I might as well use it on that hotel in case we did want to use it. San Francisco hotels can be EXPENSIVE and this one would save us nearly $300 vs the best paid rate I could find. It’s not a bad value for the $49 yearly annual fee for the credit card!

I had a second free night certificate I could use from IHG that I could also use if we ended up coming in on the Friday night instead of Saturday night. That one wasn’t about to expire so I didn’t have to book that one yet. Spending the first night or two in Fisherman’s wharf would give us easy access to the really touristy parts of the city while also letting us adjust to the time difference.

From there the itinerary would have us renting a car Sunday morning first thing and driving to Napa Valley. There are a number of things there to see and do. We were looking for a kid friendly winery tours and we found a couple that might not have been horrible. I don’t drink so my wife would have been the only one interested in the wine tasting parts.

I found a Marriott hotel in Napa that was a short walk to the downtown area that had a reasonable rate for a Sunday night. Friday and Saturday nights were MUCH more expensive. I booked a refundable rate for that property to get it locked in, but I made sure we could cancel it if things didn’t work out.

I also booked a rental car with Silvercar. I love Silvercar because you get a new, fully optioned Audi A4 to drive with navigation, satellite radio and no surcharge on any tolls you may incur. It’s so much better than a crappy subcompact and in many cases not necessarily more expensive, either. I also get a hefty 20% discount if I book with my Chase Sapphire Reserve credit card. The rental car reservation was also one that could be canceled.

Finally I booked a 5 night stay at the Palace Hotel in downtown San Francisco. I had been inside the ballroom for work meetings, but never stayed there. As a city center hotel with an indoor pool it was a unique property. The kids love having a pool to go with and the value booking on points was solid (and refundable) so I booked that as well. It’s also in a great location not far from my favorite bagel shop in the city, Posh Bagel on Sutter Street.

While we had an awesome itinerary lined up and reserved, we didn’t have plane tickets because we weren’t sure when we could actually travel on those dates. I put in reminders for several options in google flights and watched the prices over the months leading up to the trip. They weren’t getting cheaper the closer we got to the trip, unfortunately.

Second Thoughts

We still weren’t getting the final dates for games around vacation week. The flights to San Francisco were still climbing to nearly $1000 a person. There wasn’t any award availability to offset that with points, either. I tried everything I could from flying out of alternative local airports to flying out of NYC but nothing made sense.

We instead started looking at other places we could go. As much as I enjoy San Francisco, if we were going to spend that much, we should be able to go some place more exotic. We plugged in some of the same tentative dates we were looking at with Boston as the departure city, but no destination city into Google Flights. In the Map View it showed us how much it would cost to get to all sorts of different destinations.

One place that kept coming up was Los Cabos on the tip of the Baja Penninsula in Mexico. It’s a place we’d heard was beautiful and family friendly. It required a one stop flight, but was only two time zones away. It was also coming out to be about $1000 less for the family to fly to.

It was a place we had on our list and we thought would be a great opportunity for the kids to practice their Spanish skills. We also found several great Marriott properties that were available for reasonable cash prices as well as ones available on points. It was decided! Now we’d just have to figure out the actual dates of the trip!