Some of our friends think we’re super rich.

And of course, by any global or historical metric, we are (we all are). In reality things are often tight for our one-income, three-kid family.

What these friends (who, for the record, actually make >2x our income with less kids!) are thinking is:

How do you guys take such bougie trips?

Let me give you a peek behind the curtain. As a case study, we recently took a luxury-hotel-filled ten-year anniversary trip to Italy.

Turn Big Spend into Points

In 2022, the silver-lining to the death of our air conditioner was the chance to purchase a replacement mini-split with a brand new credit card. So we applied for a new Amex Platinum card, and four days later bought our $6000 mini-split with it, netting us an instant 131,000 Amex points.

Later that fall when it came time to put some down payments on two roof replacements, we applied for the IHG Business Premier card, which gave us a quick 143,000 IHG points.

Those points sat idly in our rewards accounts until we had the spark of an idea: 2 weeks. No kids. Italy.

To do it, we just needed to turn those points into tickets.

Turn Points into Tickets

Italy costs more points than other European destinations, but the nudge that pushed us over the edge was a 25% transfer bonus to Air France that popped up in Fall of ‘22 - making the Italy flights more reasonable.

Once we found some flights and dates that worked w/ our backup-child-rearers, we transferred the points from Amex to Flying Blue (Air France’s mileage program) and for 92,000 points (RT) my wife and I were on our way to Italy. But we were still homeless.

Turn Points into Hotel Rooms

With a flight into Bologna and a flight out of Rome booked, we plotted a rough north-south itinerary. Where would we stay? We let the IHG travel portal guide the way. After some exploration we landed on a few “Mr. and Mrs. Smith” estates:

Paying for roofs never looked so good. The IHG points landed us six free nights in some swanky villas.

We had to snag two AirBnBs for the last week, but at <$150/night (and with AirBnB gift cards regularly on sale for 10-15% off), we felt like we got some pretty good value.

Not Totally Free

In full transparency, money was still spent. Between car rental, gas, a sunset boat ride, credit card/ticket fees, and all the gelato and pasta in Italy, the whole thing was still over $2000. For us, that ain’t chump change.

But be honest. If this girl was willing to stay married for ten years, wouldn’t you take her to Italy, too?!