Drew and I regularly spend entire weekends obsessively planning and scheming every travel detail.  Case in point: today, I’m working at home and Drew is working on some flight research for our trip to the US in May/June.  We are planning a pretty epic trip, but we only have two specific commitments – one wedding in Colorado, and one wedding in Maine. Two weeks between the two weddings. Not so bad, right?Well, as of this minute, there are, count ‘em, thirteen flight/car options that Drew has detailed out on a spreadsheet, using cash and miles and points on multiple airlines to hack our way to the best possible and most convenient fare.  He has ten tabs open on Safari and dealing with different currencies, which he is then converting all to pounds.  Confusing.

We have one option where we fly to Los Angeles, rent a car for three weeks, and fly back to London from Boston. This gives us ultimate flexibility but also requires mucho time in the car.

We have another option where we flight hop from London to Los Angeles to Denver to Chicago to New York and from Boston to London, renting cars in each major city. That is actually the cheapest flight but requires us to use a ton of points and deal with four separate car rentals.

I’m imagining my sister Laura’s face as she reads this post later today. For her, this is straight up torture. I literally can’t think of anything she would rather do less than sit here with Drew working on the spreadsheet. As the quick decision maker of this duo, I just want Drew to give me the winning combo and book it already. But Drew is methodical and surgical with his research, though he just informed me that he’s ‘dangerously close’ to a solution.

I wonder if we were multi-gazillionaires, if we would not bother ourselves with this type of research, instead calling on our personal assistants to book just the most luxurious option. Who am I kidding? Given our spreadsheet-focused personalities, it wouldn’t make the slightest difference.  We will be listing out thirteen flight options for every major itinerary until the day we die.

Oh, Drew tells me he’s found the ideal combination, so hopefully we can book these flights soon and move on to my favourite part of the travel planning process: restaurant selection and hotel booking!