How to Blow $4,000 on a $56 Vacation

It’s All Too Easy to Do

When people go on vacation, they often pay face value. According to Forbes, the average vacation costs $1,145 per person or $4,580 for a family of four. I love family vacations because I like going on an adventure with my wife and kids. But I would never consider paying over $4,000 for a vacation. And I don’t want you to, either.

The three kids and I on the beach during our vacation to San Diego

On my last two family vacations combined, I spent less than $100 total on hotels and flights. Earlier this year, we took a $5,000+ vacation to Cabo San Lucas for $42. Last week, we took a short (2 night) vacation to San Diego for $56. Had we paid face value, the hotel and flights would have cost $4,012.

If vacations are part of your life—or if you’d like them to be—you should seriously consider a total paradigm shift in terms of how much you think they need to cost.

In this post I’ll share how we spent so little on a great vacation. And I’ll show how you can do similarly.

Our Hotel in San Diego

We stayed at the Fairmont Grand Del Mar in San Diego. It’s a 5-star hotel with nearly perfect TripAdvisor ratings from over 1,700 reviewers.

Fairmont Grand Del Mar hallway, off the lobby

We stayed in a 1000 square foot “Prado Suite.” At the time I booked the room, the cash rate, including tax, was a whopping $2,827 for 2 nights—$1,413 per night!

But we paid $0.

Back in January, my wife got the now discontinued Chase Fairmont Credit Card. Included among its benefits were 2 free nights at any Fairmont hotel and one free suite upgrade certificate. By combining those benefits, we were able to book 2 free nights in a suite at the Fairmont Grand Del Mar.

Fairmont Grand Del Mar library, where I spent a lot of leisure time reading . . . or not!

How You Can Do Similarly on a Hotel Stay

There are many hotel credit cards. But if you’re looking for one that provides an opportunity for an over-the-top room for two nights, I’d suggest the IHG Rewards Club Select by Chase.

With the IHG card, you get 80,000 points after spending $1,000 on purchases within the first 3 months. The top IHGs in the world can be booked for 60,000 points, so the signup bonus is worth at least 1 night at a top IHG. But it gets better.

The card comes with no annual fee the first year. Each year thereafter, the annual fee is $49. But in exchange for paying the annual fee, you get a certificate that can be redeemed during that cardmember year for 1 night at any IGH in the world.

So by getting the signup bonus and then paying the annual fee when it comes due, you will be able (in your second year of card membership) to book any IHG in the world for 2 nights. (Or get the card at the same time your spouse does for twice the effect.)

Probably the best redemption from a dollars/point standpoint is the InterContinental Thalasso in Bora Bora, where you can book straight into an overwater bungalow. Rates at that property can exceed $900/night. For other top IHG properties—including ones closer to home—check out the Category 10 & 11 properties shown on Travel Is Free’s excellent Complete Map of IHG Rewards Hotels.

Michael, Elizabeth, and John outside the Fairmont Grand Del Mar

Our Flights to/from San Diego

Ok, back to our trip.

Roundtrip, nonstop flights from Denver to San Diego on Southwest would have cost $237/person—$1,185 for our family of 5.

Instead, we came out of pocket $56, which is just the cost of the government-imposed September 11th security fee of $5.60 per ticket each way (i.e., 5 passengers x 2 ways x $5.60 each way).

I am the system. My boys are gaming the system.

We paid for the bulk of the tickets using 43,716 Southwest points. That was the number of points we spent to book tickets for my wife, one of our sons, and me.

Our other son and our daughter traveled for free (zero points), as Sarah and I each have a Southwest Companion Pass. Arguably the best deal in travel, the Companion Pass allows one passenger to fly for free with the passholder on any flight, regardless of whether the flight was booked with cash or points.

So, to recap, we used 43,716 points to book roundtrip tickets for three of us. The other two flew free as Sarah’s and my companions. And we paid $56 to cover the security fee on all 5 roundtrip tickets.

My son John is an early riser. I don’t know how this happened.

How You Can Do Similarly on Flights

The easiest way to get the Southwest Companion Pass is to earn 110,000 Southwest points in one calendar year. The pass is good for the remainder of the year in which you earn it as well as all of the following year.

And the easiest way to earn 110,000 Southwest points is to sign up for two Southwest Airlines credit cards in the same calendar year. There are three cards for which one can apply:

  • Southwest Plus. 60,000 points after spending $2,000 on purchases in the first 3 months. $69 annual fee.
  • Southwest Premier. 60,000 points after spending $2,000 on purchases in the first 3 months. $99 annual fee.
  • Southwest Premier Business. 60,000 points after spending $3,000 on purchases in the first 3 months. $99 annual fee.

If you’re interested in getting a Companion Pass via two credit card signups, however, I’d recommend waiting. That’s because to maximize the benefit of the Companion Pass, you want to earn it as early in a calendar year as possible. Doing so allows a companion to travel free with you for almost two whole years. Earning it at this point in the year isn’t ideal.

If a better opportunity arises to earn the companion pass (which it likely will), I’ll be sure to let you know. Sign up for my newsletter to receive that alert by email.


If you enjoy vacations, go on them. Just please, don’t pay $4k. Put that money to better use on other priorities.

Question: What is keeping you from moving from a mindset that vacations cost $4,000 (or $1,000+ for an individual) to a mindset of them costing under $100? You can leave a comment by clicking here.

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7 thoughts on “How to Blow $4,000 on a $56 Vacation

  1. I’m quite curious to see how your travel on the cheap evolves as the kids get bigger. I’ve found traveling with six of us (mostly-bigs) has created major challenges. Finding lodging to accommodate all of us (they are not quite big enough for me to be comfortable taking a chance at connecting-room bookings) is an adventure in and of itself. Paying for meals is a major chunk of travel expense, with the best case scenario at $50/meal. I love that we have always traveled with them, but now they/we have expectations of adventure, it’s become much more difficult to travel for next-to-nothing!

    • Carole,

      I’ve had those same thoughts and am likewise interested to see how travel evolves for my family.

      A few thoughts I’ve had in that regard so far include:

      • If my family is to stay in one room, that room will need to be a one-bedroom suite or larger. Therefore, programs whose points allow me to book directly into a suite (e.g., Hyatt) rise in value.

      • We could get connecting rooms. Or, at least, I figured that would be a good play for us. I’d be interested to hear more about what you mean by that not necessarily being a great setup.

      • We’ll probably be more likely to look at non-hotel options such as renting homes on Airbnb or VRBO. I know points can help defray such costs, but I’ll need to research how to maximize those opportunities. (And I’m hoping that new opportunities/cards emerge as Airbnb and VRBO continue to establish their prominence.)

      • I’d also like to explore very different options for adventure, such as renting an RV. At a certain age for the kids, even just road trips in our minivan will probably be fun.

      It’s tough to imagine that travel won’t get harder / more expensive as my family grows. But I look forward to the challenge of trying to figure out how to do it on the cheap.

      Oh, last thought. Regarding meals, a good trick is to charge hotel meals to the room and then use a card that reimburses travel costs to pay the bill on the room. That’s what we did at the Fairmont, using the Barclay Arrival+ card to pay the room bill, which consisted entirely of food charged to the room. Not infinitely scalable, but helpful.

      Thanks for the comment!

      • Regarding the connecting rooms – my understanding is that even at family-friendly venues (e.g. Disney) there is no guarantee for rooms that are next to each other or that actually connect – I imagine trying to use reward nights gets even trickier. Our age range is 8, 11, 15, and 17. There is a curious feeling when one’s child is a bit too young to have access to an outside door (or the chance that there is a second entrance/exit), but then on the immediate other side of that dilemma, they become slightly older and may decide they are big enough to go exploring at an odd moment. Some parents are okay with that risk. Also, my husband and I decided we really don’t want to do the one adult in each room thing – another possibility!

        Sneaking in more than the max cap has become problematic! 🙂 IHG, SPG, Hilton (Doubletree, etc) have had the best options for reward nights that can be upgraded to 3 beds. We haven’t gone the Airbnb route yet because it doesn’t offer a straight free night, but it’s definitely in the cards.

        • That all makes sense. I appreciate the concern with kids that age. Good to know IHG, SPG, and those certain Hilton properties have allowed upgrades to 3 beds. Thanks for sharing!

  2. Hi Brian, what do you think about cards like the Marriott Rewards Premier Credit Card (80,000 points, $85 annual fee, spend $3K in first 3 months, free anniversary night stay) or the Hilton Honors American Express Surpass Credit Card (100,000 points, $75 annual fee, spend $3K in first 3 months, free anniversary night stay)? I came across them while looking into the IHG card. Are these all about as good as the others? If so, do you just sign up for as many as you can reasonably meet the spend quota for? Also, amidst all these credit card deals, do you have a particular credit card(s) that you keep as “permanent” while you just rotate through these other cards (because for most of them it seems you can’t take advantage of the deals if it’s been less than 24 months since you were a cardholder–which seems to be motivation to cancel the card once you’ve received the benefits)? I’m thinking maybe the Southwest one? Lastly, is there a max # of open (1) credit card accounts and (2) rewards points programs you recommend having at one time so that the time required to keep track of the accounts and rewards programs doesn’t outweigh the benefits? Thanks!

    • Steve,

      Thanks again for these questions. I apologize for my delay in replying to them.

      I, personally, prefer hotel credit cards that come with points rather than free night certificates. With points, you have the flexibility to spend them for more nights at slightly lower-tier properties vs. with free night certificates where you only get 1 free night no matter the property. Also, free night certificates expire whereas points do not (as long as you periodically generate some point activity). I mentioned the IHG card because it’s free night certificate can enable, each year, the type of high-end stay that my family enjoyed with the Fairmont free night certificates. A lot of folks really enjoy those high-end splurges.

      In terms of how many cards to sign up for, provided that one has a good credit score, yes, the limiting factor is one’s ability to meet the cards’ required minimum spend. But there are tricks for that, too. See:

      I do keep some cards long-term. Those are typically premium cards that I have “downgraded” to no-annual-fee cards in order to avoid paying an annual fee beyond the first year. It’s also ideal, from what I’ve heard, to keep open the oldest card you have.

      Finally, I agree that one shouldn’t open more cards than one can properly manage. With a robust tracking system, I think that number can be fairly high, and the benefits of developing a good tracking system can be well worth it. That said, it’s important to know oneself in this regard.