Why The Advice You’re Getting is WRONG, Here’s The Best Way To Really Maximize Your PTO!

Okay this has been bugging me since it’s been making the rounds on social media. You’ve seen them too right? Those 2026 guides on how to turn 17 days of PTO into 48 days of vacation paired with the US Holiday schedule or other XX PTO days into XX vacation days?

What do I hate about these guides? That they always tell you to take the Friday off before a Monday holiday! Come with me as I show you why you should requests Tuesday for your long Presidents’ Day weekend plus a look at why flexible points are so valuable and how you can get some without a credit card!

Los Cabos, Mexico (Flying DEN – SJD)

Here’s why that is such bad advice. Here’s what flights from Denver, Colorado, US (DEN) to San Jose de Cabo, Mexico (SJD) over that weekend look like – first with the conventional advice and then with my advice.

See why I hate this advice?! Flying on Fridays and Mondays makes for some expensive vacation which is true if you are using cash or points!

So what you should be doing: requesting Tuesday (and if you can swing it, Wednesday). I know, you are wondering if it really makes a difference?

Flying out on Saturdays is typically cheaper than flying out on Fridays (and Sundays!). The same is true for flying on Tuesdays (and Wednesdays) than on Mondays even when it isn’t a holiday weekend! The difference between both cash prices (even if you are looking at all carriers/cheapest flights!) and miles needed is insane!

Flexible Points (and airline alliances) FTW

This is why flexible points (those you earn through Chase, Amex, Bilt etc that you can transfer to one of the travel partners) holds significantly more value than just earning UA miles on your United credit card. The cheapest flight on Saturday from DEN – SJD 2/14 is 27.8K miles (note this is per person) and this is not a direct flight.

Airlines alliances were created to allow you to seamlessly travel in different parts of the world on one ticket. What it also created was a gold mine of opportunity for us who love travel hacking.

Weirdly true that often the cheapest flights (ie less amount of points needed) is often an airline’s alliance partner. And in this case, if you search Air Canada for the same date, Saturday 2/14) you would only need 15K/pp Air Canada miles and you would fly direct from DEN – SJD and it would be on United. Wild right?! And while Chase has never done a transfer bonus to United, there are regular bonuses on Air Canada making your points even further!

Where to stay in Cabo? Hint: use your Hilton Free Night Award!

Mexico City, Mexico (Flying IAH – MEX)

Here’s another example flying from Houston, Texas, US to Mexico City, Mexico over the same President’s Day weekend.

Here are the cash prices from IAH – MEX round trip 2/13-2/16/26 for 2 people and round trip 2/14-2/17/26 for 2 people with a $300 difference

Flexible Points Again Showing Their Value

This must be a popular route for United as there are many, many direct flights from IAH to MEX with very great redemption rates. But here’s where things get interesting while the alliance partner trick doesn’t work in this case as Air Canada is not cheaper than United, there are Aeromexico flights bookable via Flying Blue (Air France / KLM’s loyalty program) for 8.5K (the show the total needed for # of passengers you choose).

You are thinking that’s not significant savings but again Chase/Amex/Citi and CapitalOne have had transfer bonuses in the past and Chase has never had one with United PLUS many hoard their Chase points…why coming up.

Where to Stay?

I have been trying to make a trip to Mexico City (CDMX) work for awhile now and there’s a couple of attractive options available. And this is why people love Hyatt and want to transfer their Chase points. A still reasonable (and published!) award chart!

Booked a room with Hyatt that has a lounge AND your stay is done completed by 2/26/26?

How to Earn Flexible Points WITHOUT a Credit Card

I wrote about the new Rakuten and Bilt partnership a couple weeks ago but this is a good time to mention it again as you can opt to have your Rakuten cashback in Bilt points!! For all the details read this!

f you’re not yet a member of Rakuten, I’d recommend signing up through a refer a friend link before you set up your account for this partnership. That’s because the current refer a friend bonus gets you $50 in rewards (5,000 Bilt points) upon completing eligible activity, while Bilt’s offer only gets you 2,500 Bilt points in rewards.