Easiest travel hack regarding Hawaii: Go in the shoulder seasons. (Weeks preceding summer vacation, weeks right after summer vacation)
If you’re really adventurous, consider a trip during hurricane season as hotel rates get nice and (relatively) cheap and rental cars even cheaper.
Makes sense. Unfortunately we’re not as flexible about travel dates this year due to an expected baby. 
Also try to avoid spring break - Hawaii is a heavy destination from the PNW and similar during late march to mid-april.
Big congrats!
Thanks!
Congrats, Make it a babymoon!
Also, AirBnB is also a great option if you feel you need more room than your average hotel room will afford.
This or try to “buy” someone’s timeshare for a week. I cannot tell you how big a difference it makes in the cost of a Hawaii trip to be able to eat breakfast, lunch, snacks etc in your room with a full kitchen.
Thanks! That’s definitely the plan Yea, I really should look at AirBnB. I never really think about that.
And DEFINITELY avoid xmas/NYE! Been there done that, had the credit card bill to show for it. This is when old money descends on the islands and makes your middle class money look like a charity case. Next to impossible to score suite upgrades as a top tier elite because they’ve been bought out.
Interesting! How do you do that? I’ve seen on orbitz where condos are basically rented out as hotel rooms, but I’ve never seen anything about outright buying a timeshare for a week.
The larger timeshare companies often also have packages to bring you there that give you a week’s worth of nights for 30-50% regular price, just gotta go to a presentation and do your damndest to say no.
Any tips for Paris? I feel like I’ve hacked all I can just by staying in airbnbs vs hotels, utilizing metro, etc.
My main dream in life is flight upgrades but somehow I’m never that person getting bumped to business
Flight upgrades on long haul are hard enough to get as an elite. I’d advise to just hoard points or search often for cheaper fares and be flexible on your travel dates.
I cashed out a bunch of points for a business class transatlantic flight once… spoiled me for life though I still had to pay nearly 2 grand in taxes for the damn thing.
Booked on British Airways, didn’t you.
Hoard points, book last minute to get last minute released upper cabin award space, and be flexible. Getting harder all the time for the cheap reward seats.
Bet you used BA Avios or AA miles on BA metal. Bad idea.
I never use Avios on anything but domestic AA flights, no close in fee is wonderful.
Virgin Atlantic…It’s a UK thing I think
Ah…
Yeah, LHR has a steep tax on premium seats when flying flag carriers.
Always avoid flying into London so you don’t have to pick up those fees. But hey — if you’re not a big time traveler, it’s worth traveling a premium cabin at least once for the experience!
Actually Air France economy wasn’t so bad and flying direct from LA was nice… not laying in a bed nice, but 1/8th the price nice.