2018 Summer Travel Planning is Underway.


It’s August, new sets of students are coming this week, and so it’s time to begin thinking about next summer’s unemployment.  I’ve got a bunch of miles, with a bunch of airlines, but it is difficult to redeem miles in the summer, especially for a family of 4, with a preference for first class flights.

In the JumpStart family, trip destinations are typically chosen based on free flights.

A few years ago we flew to Saint Thomas, the day after Easter.  Saint Thomas was great, but there are lots of Caribbean options. When I found 4 saver level American Airlines award flights from Roanoke to Charlotte to Saint Thomas, there was no hesitation, and I booked them immediately.  Months later, a couple credit card bonuses earned us three free nights at the Ritz Carlton.  Next, I located free flights back to Miami with British Airways miles, and a free Marriott hotel in Fort Lauderdale. Finally, I was able snag Mrs. JumpStart and JumpStart Jill an award flight in first class on United home.  JumpStart Jack and I never found a reward flight home, and were forced to purchase Delta tickets for $150 each.  $300 for a family of 4 to fly, spend 3 nights in Saint Thomas, and 3 nights in Fort Lauderdale is pretty good though.

In that spirit, I booked a one way trip today.

100,000 American Airline miles and $22.40. Charleston to Los Angeles with a short layover in Seattle.

Both flights are in first class, and on Alaskan Airlines planes.

In the end, one of my credit cards gives a 10% bonus on redeemed American Airlines miles, and I got 10,000 miles back, for a total of 90,000 miles and $22.40.

As usual, we will spend more on gas driving to South Carolina and a taxi in Los Angeles, than we spend on plane tickets.

Next task is finding free flights home.  Southwest also flies from the Charleston airport, and we’re expecting 125,000 Rapid Rewards miles and a companion pass as soon as the Chase billing statements close.

Southwest doesn’t schedule flights out as far as other airlines, and therefore I’ll have to wait a few months to check their flight choices.  Southwest is always an dependable option, because award flights are based on purchase price, and not subject to blackout dates.  However I would prefer to find first class on Alaska, United, Delta, or American.

Our return flight doesn’t need to leave from LAX.  San Diego, San Francisco, and Las Vegas are great options.  If I can’t find 4 seats on the same planes, it’s always an option to send part of the family straight home to Roanoke.

Once our return flight date and city are finalized, I can begin the search for great free hotels.  The only part of California I’ve ever visited is the San Francisco airport, and we are excited.

Posted in Trip Report.


  1. Interesting. I’ve always had the same problem but am never able to convince myself to book oneways and then figure the rest out later. I take that approach with my investing but not with travel – ha!
    I almost always have to figure out at least the round trip before spending the award flights. I guess it’s worth trying this approach out – stuff generally falls into place (in most cases).

    • We have a unique situation as 2 teachers being unemployed for a 2 month stretch in the summer. I am also comforted by the the variety of miles/point types I have accumulated over the last 4 years. Finding award nights is pretty easy. The flight home will be tougher, but there is a lot of time to figure it out. Worst case scenario, we walk home.

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