We have some friends that are new to the points and miles game and we often chat about trips they’ve made as well as our trips. They had recently come back from a trip to San Francisco which they had used points earned from their JetBlue card.

Looking to JetBlue

While the JetBlue card isn’t the best way to earn JetBlue points, the card itself provides a relatively good value proposition just by holding it. For one, you get a free checked bag for everyone in your party (up to 4). That can easily save you the cost of the annual fee after just one flight. In addition, you get bonus points as a cardmember anniversary gift. JetBlue points don’t expire and you can pool points with friends and family. To top it off you get a 10% rebate on any points you use to book flights, which can add up if you earn and spend a lot of points.

Since JetBlue is the biggest airlines in Boston, there are lots of opportunities to use the airline. I enjoy flying them as they go to the places I need to for work (primarily San Francisco, New York, and Chicago) and the planes offer extra legroom, even in the cheap seats in coach. Being 6′ 2″, it really helps to not have my knees crushed against the seat in front of me when I’m on a red-eye home from the west coast, so I try to choose them for those flights whenever possible. Our original thinking was taking a red-eye on this trip so we would look to fly them anyways.

Given all that, it makes sense for us to get this card so I had my wife sign up for it. At the time it came with 50,000 points after spending $2000 in the first 3 months. Since we were planning to fly JetBlue anyways, the free checked bags would more than compensate for the annual fee so it was a no-brainer.

Getting to San Francisco

While the schools discourage skipping school in the day or days before holiday vacation, we’ve found that those days usually are scheduled with movies, pajama days, and other activities focused more around filling the time than actual education. We were looking to head out either the Friday before a vacation or better yet, Thursday evening after school. It would be the classic getaway flight!

Google Flights was my friend in searching for itineraries. I was looking for a flight to San Francisco, then a flight from San Francisco to San Diego and then one returning to Boston from Los Angeles. Entering a multi-destination flight itinerary in Google Flights made this relatively easy to find the options and narrow down the best prices.

As it turned out, one of the cheaper flights to San Francisco was on Thursday at 6:05pm. It was even cheaper than the later 9:00pm flight that arrived after midnight. While we would have to leave as soon as the kids got home from school, we’d still be able to make it comfortably even if we encountered holiday travel. We’d arrive around 10pm in San Francisco which is pretty reasonable for us. To top it off, this flight was a JetBlue flight so we could use the card to get the free checked bags.

Getting to San Diego

We wanted to be in San Francisco for about 5 nights which would have us leaving for San Deigo on Christmas Eve. We didn’t consider driving because it would have taken too long. Also, the flight prices were about $100 per person so it was not going to save us much money by driving anyways. Given it would be on Christmas even, we preferred a direct flight. That wasn’t an option with JetBlue out of San Francisco or Oakland. I checked several other options and our best bet was on United. Since my wife has status with United via her Marriott Titanium status we could also get a free checked bag per person. That was also a benefit of my United MileagePlus Explorer card so we were covered two ways for checked bags there.

The flights were cheap and they are short. I also made sure I did NOT get the Basic Economy ticket and paid more for the regular ticket. The reason is that if there are delays or cancellations, you have much more flexibility and priority if you do not have the basic economy ticket. Christmas Eve is not a time to be hoping a seat opens up on a flight.

We also were careful to make sure we weren’t the last flight out. I close a 6pm departure which would give us a solid day in San Francisco, give us an early evening arrival in San Diego and also give us a buffer if there were delays or cancellations since there were two flights after ours. I also put the flight on my Chase Sapphire Reserve card which has excellent flight delay and flight cancellation insurance benefits.

Getting back to Boston

We were going to spend a few days in San Diego and then rent a car to drive up to Santa Barbara for 5 nights around New Years before heading home from Los Angeles. I was originally thinking of taking a red-eye back on the Sunday before school started on the first Monday of the new year, but those flights were already pretty full. I instead looked at a Saturday night red-eye. Those prices were pretty expensive as well and saw the mid-afternoon flight on the Saturday was by far the cheapest option. The times were comfortable for us as we could have a relaxing morning getting to the airport and a nice flight back with a day to re-adjust before getting back into the swing of things. This flight was also on JetBlue which again meant we could check our bags for free.

I ended up booking these flight segments separately. I booked the JetBlue flights using my wife’s JetBlue card (under her account of course) and also booked the United flights under her account to make sure we got the free checked bag benefits there as well. Overall the flights totaled just over $2000 total, which was about what we were looking at per person on our Asian trip.

While we wouldn’t be going anyplace nearly as exotic, there would be plenty to do and the boys would be able to spend Christmas with their uncle.