Booking Italy for four on 189,000 points and $1,874

I usually book for one. Solo trips, or trips with friends where everybody handles their own flights. Sometimes two, me and my partner.

Four is a whole 'nother animal.

I'd never done it before this challenge, and I came out the other side with a newfound appreciation for anyone booking for a family. Here we go.

First, my one rule about fees

Before I show you the trip, you should know the bias I brought to every single decision in it.

My personal philosophy is that I try to pay as little in fees as possible, because it doesn't make sense to me to use miles and still have to pay hundreds of dollars out of pocket. 🤷‍♀️

That rule cost me options on this trip. I'd make the same call again. It's also why I didn't land on the cheapest-in-points itinerary, which you'll see in a minute.

Okay. Now the trip.

Pompeii, and why Italy was an easy yes

In what feels like a previous life, I was an archaeologist.

So visiting Pompeii is absolutely a rite of passage, and the second I saw Italy on the board I knew Naples was going in the itinerary whether or not the points cooperated.

They cooperated. Barely, and only because of a transfer bonus. More on that when we get there.

The rules, and the thing that makes four people tough to wrangle

Quick refresher on the challenge: four travelers, departing the East Coast, Thanksgiving week, on a budget of 200,000 points and $2,000, with points from at most three credit cards.

I used all three. The Chase Sapphire Reserve®, the American Express® Gold Card, and the Bilt Obsidian Card.

I picked Boston as my departure airport, since it had the best options when I was looking.

And here's the part that changes everything about booking for four instead of one: I needed four of everything. Four award seats on the same flight, four beds in the same place, four train tickets. A single seat at a great price is useless to me. Scraps of availability are useless to me.

Which is how transfer bonuses stopped being a nice-to-have on this trip and became the entire strategy.

Getting there: three options, and why I took the one in the middle

Option #1: Flying Blue. 106,000 miles + $134.

Low fees, which I'm a big fan of. But it slashed my mileage balance by half right from the start.

Option #2: Virgin Atlantic plus Ryanair. 24,000 points + $1,075.

This was the least number of points for getting across the pond, with a cash positioning flight on the other end, since there are so many cheap inter-European flight options.

But it slashed my cash budget by half right off the bat, and I couldn't make it work with everything else I had to book. See also: my one rule about fees.

Option #3, the winner: Aer Lingus on points, Aer Lingus on cash.

Here's the math. It came out to 52,000 points total, 13,000 each. BUT I used the current transfer bonus from Membership Rewards to Aer Lingus, which brought that down to 40,000 points.

Add taxes and fees of $424, plus $316 for the Dublin to Rome leg at $79 per person, and we're at 40,000 points + $740 to get all four of us there.

I always like to compare against what the cash option would cost. The cheapest was $734 per person, or $2,936 total, which would have eaten the entire $2,000 cash budget before I booked a single hotel.

Rome: three nights in an apartment for $590

We land in Rome on 11/22. Whoot!

For a group of four, an apartment is almost always going to be the most economical and the most comfortable option. Four adults, one bathroom, no thank you.

I found this one on Rove with a nice 12x multiplier.

$590 for three nights, and the perfect base for seeing all the sights.

Naples: Pompeii, and the 70% bonus that came in clutch

On 11/25 we take the train to Naples, one hour from Rome, $92 total for all four of us.

Two nights, and Pompeii. (Told you.)

The Holiday Inn in Naples is not the most glamorous stay of this trip and I do not care even a little, because it came in clutch.

I used the 70% Ultimate Rewards to IHG transfer bonus. I missed the 100%. Hey, that's life. 🤷‍♀️

40,000 IHG points for two nights at 20,000 a night became 23,530 Ultimate Rewards points, which became 24,000, because you have to transfer in 1,000-point increments.

That bonus is the whole reason Naples happened. Without it, Pompeii comes off the itinerary and I write a sadder article.

Then the same train back to Rome on 11/27, same $92 for all four.

One last night in Rome, for 15,000 points

Chill out for the last night at an airport hotel in Rome.

Once again, that 70% IHG transfer bonus. 14,706 points, rounded up to 15,000 for the transfer increment.

Not romantic. Extremely practical when you've got a morning flight and three other people to get to an airport.

Getting home: 110,000 points I really didn't want to spend

I'll be honest: by the end of a busy trip, I just want the most direct route home if I can manage it. No positioning. Shortest possible path to my bed and my cats.

Honestly, I couldn't find anything better anyway. The weekend after Thanksgiving is a rough time to travel.

110,000 points + $360 for all four of us.

Two things worth knowing about that number.

First, it's nearly triple what we paid to get over there. Same four people, same trip, one week apart. That's not a booking mistake, that's just what the Sunday after Thanksgiving costs.

Second, Aer Lingus was the only other viable option flying back, at 66,154 points + $942 for all four passengers. Fewer points, but the fees put me over the $2,000 budget.

The damage

189,000 points. $1,874 cash. $126 left over.

Plus 10,525 points earned along the way, which softens it a little. (You can take the girl out of Points Pursuit, but you can’t take Points Pursuit out of the girl.)

What didn't make the cut

• Flying Blue at 106,000 miles, for cutting my points balance in half on day one.

• Virgin plus Ryanair at 24,000 points, for cutting my cash budget in half on day one. Genuinely the cleverest option on the board, and I still couldn't make it fit.

• Paying cash for the flights, at $2,936 for four. More than my entire cash budget, by itself.

• Aer Lingus on the way home, at 66,154 points + $942. Lost on fees.

• The 100% IHG transfer bonus, which I missed by timing. It happens.

The bottom line

I never have to book for a group of four, and it was eye-opening how hard you have to lean on transfer bonuses when you're traveling with a family on fixed dates.

Holiday Inns booked through a 70% IHG transfer bonus saved me. Twice.

And I had to weigh points against cash on every single flight in a way I never do for myself, because I'm points flush and I'd rather pay as little out of pocket as possible.

If I'd booked this trip for me, it would be a completely different trip. Which is sort of the whole point.

To everyone booking four seats at a time on fixed dates: I see you now. 🤝