We had our flights booked so we had the dates we needed to fill with hotel stays. We had 5 nights in San Francisco that was definite. Then we had 11 nights to fill between San Diego and Santa Barbara.

We often try to plan stays in 5-night increments because when paying with points at Marriott we get the 5th night free which really adds value. We expected to use points for at least some of the stays.

San Francisco

San Francisco is a notoriously expensive city and we expected that using points was going to be our best bet.  As I started searching, I found the cash rates were surprisingly low. There were several really nice hotels in the Union Square area that were $200/night or less.  Points wouldn’t have provided a great return even with the 5th night free. Many times when I visit for work these same hotels are going for more than twice as much for cash rates.

I found the best option for us was at the JW Marriott Marquis. They had upgraded rooms with two queen beds instead of double beds. The extra space can be priceless with keeping the boys from fighting (as much). This upgraded room was $180/night on a refundable AAA rate. In general, we find the Union Square area to be conveniently located and not quite as touristy as Fishermans Wharf, which can be pretty dead after the sun goes down so I booked this rate.

San Diego

In San Diego, my brother in law was going to be staying with us so ideally I needed to find a hotel room that could hold all 5 of us. I was worried that was going to be a challenge and it certainly limited our options, but there was one Marriott hotel that fit the bill. The SpringHill Suites is located downtown, holds 5 people, has free breakfast for all, has a pool, is near to a park, walking distance to several attractions, and very close to many restaurants. It was built relatively recently so it looked in fantastic condition in the pictures. The refundable AAA rate was only $150/night. I booked this for 4 nights.

Palm Springs

I booked the San Diego room for only 4 nights because we decided we wanted to spend a couple nights in Palm Springs. It’s a place we had never been before and it is partway to Santa Barbara and would reduce the length of the drive there (hopefully). My wife isn’t a fan on long road trips so it’s a big plus.

It is also a place that seems like there are some interesting things to do so I started looking for hotels. There were a few lower-end Marriott hotels we looked at which held 5 people (my brother in law would still be with us for at least one of the days), but they weren’t all that exciting. The Fairfield Inn looked like a nice property, but it’s not much of a destination property.  We were in the mood for something more interesting for 2 nights.

In the end we settled on the JW Marriott Desert Springs Resort. I had read about the property in one of the blogs I read and remembered mention of a water shuttle/gondola to take you from the lobby to different parts of the property. I also remember mention of free mini-golf and a spectacular pool area. From the sounds of it, the boys would LOVE it for sure!

In order to get a room that held 5 people we needed to get a suite which was a little more expensive at about $350/night on a refundable AAA rate, but it was only two nights and the resort seemed like a memorable destination. We couldn’t use points to get the suite we needed so I booked the AAA rate.

Santa Barbara

We wanted to end our journey in style and had read excellent things about the Ritz Carlton in Santa Barbara from several sources. The cash rates at the hotel are high which meant it was an excellent candidate for using points. For this, my dad wanted to let us use his points for that stay as a Christmas present. He booked the stay using his points and called to add my wife’s name to the reservation so we could get her elite benefits for the stay.

The hotels were all set, or so we thought…