Brad I hear you, during my StillSecure years I averaged about 120 to 150k miles a year and that was 99% domestic. The best it ever worked was when we used a private travel agent. There is just no good technology solution. All of the mobile apps, all of the web stuff, doesn’t take the place of just telling someone this is what I want, make it happen.

Jen does this for me when I travel, too. It is super difficult, but the tricks she uses are probably the same. We optimize for convenience + cost.

She uses Expedia, the airline’s, rental car co’s and hotel’s web sites. We find that hotels + rental car cos, on the whole, hate Expedia + the like. There’s a universal issue (around costs + paperwork, I think) w/ this that creates a dis-incentive for the cos to sell thru the 3rd party sites. We almost always get better rates booking directly w/ the hotels + rental car cos, but that usually means a little more hassle upfront, as we have to do the itinerary piece-meal. For a year of travel, this generates enough savings to be worthwhile.

That said:

- For day trips + those where your hotel is reasonably near the airport, use cabs or Uber. That removes the need for any rental car + associated hassle

- If you do need a rental car, book one at same time as flights, but then check rates again a day or two before travel. You can often get the exact same car (or better) for less, because the rental car cos are trying to book expiring inventory. This has saved me a ton of cash over the years.

- Avoid the airlines that consistently have poor service + dirty planes. Out of DEN, this means United. For me, this meant switching exclusively to Frontier for several years of DEN-SFO travel. Huge diff in pleasure-of-travel quotient.

- Use a car service to/from DEN so you don’t have to deal with parking. Be sure to use a reputable service here – the whole point is to reduce stress + that gets destroyed if your driver is late or a no-show.

- If you do drive yourself to DEN, always, always, always park in the garage. The $15 – $18 (or ~$35 in valet) per day is worth the stress it reduces for me in terms of dry, warm[er] access to the terminal + safety of the car (i.e. protection from hail + casual burglary)

But when I re-read your post, I don’t think any of these things are what you’re trying to improve. You want a better, easier way to manage the *scheduling* aspects of travel, right?

Clarifying this a bit wld be helpful.

I’ve made Platinum on Delta the last several years in a row – over 75k / year – and over 80% of that travel is direct (not multi-leg) and east of the Mississippi.

My solution has been BlackBerry Travel, the private label version of WorldMate. I can’t recommend WorldMate highly enough. The performance of their parsing engine has, in my experience, been quite a bit better then TripIt.

It’s easy as pie to get set up and allows you to get around the issues that John M. notes re: the piece-meal itinerary.

Give it a (free) try, I don’t think you’ll be disappointed.

Amen – its a timesuck and I’ve never been able to find an adequate solution that even comes close to the results of doing it manually. Sounds like someone plugged into the travel world should launch the right solution, and then pitch to the Foundry Group. (please, so we can all get our time back)

I do a similar amount of travel – 4-5 flights a week with occasional trans Pacific hauls. I’ve become a big fan of Tripit. I use Kayak to map out most of my flights and then I make arrangements with AmEx travel ( a corporate requirement ). Tripit lets me just email them my itinerary and everything gets imported. Most importantly, it’ll publish to Google calendar so my wife can keep track of flights and hotels. When I have an update to my travels, I just email the changes and things get updated. They’re supposed to have a function for “travel arrangers” that I haven’t used, but might be worth looking into. I splurged and spent the $49 a year for the pro membership – it’s already let me know about cancelled flights before the airline does ( United has been horrible about this lately ).

i was on AmexTravelStore for awhile. i liked it!

It needs smart, elegant tech to help people with extremely complex and frequently changing plans.

I get the impression that AmEx and other corporate travel services, along with private travel agents have solved the problem reasonably well / cost effectively for companies with high volume, lower complexity travel. From experience they don’t do complexity or handle changes so well.

Funny, I was saying just an hour ago that TripIt are my favorite innovative travel startups before a nice early-ish exit. That’s the sorta team I’d like to see take this on.

Short answer: private jet.

More realistically, perhaps (for short haull, intra-US trips) some kind of “season pass” service could be offered, when one could walk on to any flight leg that has availability without booking? This would work particularly well for high density routes where having to wait 30 minutes for the next plane wouldn’t matter too much. Could even extend to multi-airline or airline-network validity. Perhaps there are operational or legislative reasons why this couldn’t work the way it does for railways (at least in the UK).

Buy a plane, dude.

My husband, Thomas, racks up the miles as a Futurist Keynote Speaker, and I am the “Kelly” in our company. I have been looking for something seamless and easy to use. I am constantly trying to book multiple cities both domestic and Internationally (and at times trips so I can accompany him), so I feel Kelly’s pain. I tried TripIt for awhile but didn’t care for it, so would really love to find something that works. I would even settle for a great travel agent in the Boulder area. Thanks to the mention of WorldMate. I will check into that.

I used to travel 3-5 days a week and know what you struggle with. But take those airline travel systems and say “hey I’d like to take a Train from here (midwest) to there (west coast), for a romantic vacation trip (they have wifi). How can I do that?” and find another whole layer of travel planning excitement.

I had a go at this not so long ago, came up with a service for frequent business travelers, esp ones that go on same routes often – one of the concepts was complete integration with their calendar (rather than a new interface). Imagine booking a flight similar to booking a resource on your exchange server.