Italy is the bucket-list destination to rule them all.
And I'm speaking from experience here, because it was my first trip abroad and the trip every other one inevitably gets compared to.
I've wanted to go back for years but always choose to go somewhere new instead, so I just haven't made it happen yet.
So when this challenge landed in my lap, I had the excuse to plan a trip to Italy that I’d been waiting for.
Then I looked at the calendar. 😣
First, a word about the school calendar
I worked in education for a decade, and I have the pleasure of being married to an educator, so I am extremely familiar with the pros and cons of the school calendar.
Yes, you might get summers "off." Yes, you might get long breaks around the holidays and never have to touch your PTO.
But you know who else is traveling around popular holidays? Basically everyone. 😑
So you take your less than impressive teacher salary, try to book a vacation during your bountiful time off... and you know what you get?
Expensive travel dates.
Points and miles help a lot here. But even award travel can be expensive on the weekends leading up to a holiday.
Rant over. (Mostly.)
Because in my years of wrestling travel plans into the school calendar, I've landed on the same three options every single time:
Pay more points to fly on my fixed dates from my home airport
Re-position to a different airport to save on an award flight
Take PTO and return to work a day or two late (why does this option always lose 😭)
This trip is the story of picking the third one.
The rules, and the thing that makes two people a challenge
Quick refresher: two travelers, departing Houston, Thanksgiving week, on a budget of 200,000 points and $2,000, with points from at most three cards.
And while that might sound like the challenge itself, it’s really not.
The real challenge is finding availability for 2 from the middle of the US for a price that doesn’t make you want to throw your computer across the room. Finding one decent award seat is great but does you no good if you’re not traveling solo.
So, because I value a deal, I got a little flexible with the rules of this challenge. 😬
Getting there: how 100,000+ points became 37,500
Flights from Houston (IAH) to Italy (FCO, VCE, MXP, FLR, I checked them all) over the weekend before Thanksgiving were running over 100,000 points+ for two people one-way in economy. 💀
No thank you, we will not be making that horrible redemption, friends. 🙅♀️
So, option two: re-position to the East Coast and spend 25,000 points per person, a total of 100,000 round-trip, to fly from New York.
Better. But the catch is paying for a repositioning flight and losing some of your vacation days to extra travel.
If you're a Central Timer who lives closer to Chicago, there was availability from there for 65,000 for two. Not great, but better. If you'll need to reposition anyway, though, I'd go wherever you can get the best rate possible.
Now here's the one that made me sit up.
That same flight from Houston, on Monday, November 23rd: 37,500 total points for TWO passengers.
Same route. Same airline. One day later.
So personally, if I had the flexibility to take the extra day off, I'd fly out Monday, November 23rd and fly back November 30th, and save myself thousands of points and several hundred dollars.
This is exactly why we say flexibility can be key to booking better award fares.
And it gets better, because by taking advantage of the 20% transfer bonus from ThankYou Points to Flying Blue, those points go even further. 75,000 points becomes just 63,000.
One more thing nobody puts in the pro column: you get your weekend back. You can spend it decompressing, cleaning, packing, and getting things sorted for when you return, instead of taking off first thing Saturday morning.
An unrushed ease into your vacation is a special little luxury, if you ask me. 🤷♀️
Tuscany: a former monastery for 22,125 points a night
If I spend 63,000 points on round-trip flights, that leaves 137,000 for lodging.
I spent a week in Tuscany on that first trip to Europe years ago and fell in love. I've wanted to go back and explore more of the region ever since, so that's exactly what I'd do.
Fly into Florence, pick up the rental car, and head straight into the Tuscan countryside.
Partly because I love slowing down in smaller towns and villages. And partly because this resort between Florence and Lucca looks amazing.
Once a former monastery, this hotel and spa is doing relaxed luxury right, with plenty of rave reviews to back that claim up. The perfect place to unwind for a few days and visit the towns we missed last time, like Lucca and Pisa.
And because it's a Mr & Mrs Smith property, it's bookable via Hyatt at just 22,125 points a night.
Meaning I can easily swing at least 3 nights here. Thanks, Hyatt. 😘
Rome: 20,000 a night and a walk after dinner
After 3 days of villages and slow mornings, I'd head back to Florence, return the rental car, sightsee if I had time, and jump on a train to Rome.
We blitzed through Rome last time and missed a few things, so I want to go back and see more of the Eternal City.
I'd stick with my bff Hyatt and stay at The Tribune, a JdV by Hyatt property near Villa Borghese.
It's a little further from the main tourist attractions, but it's quieter, and I never got to explore the Borghese gallery or gardens last go around.
Plus, a nice walk after dinner is one of my favorite European pastimes. ☺️
The damage
Points: 63,000 (ThankYou → Flying Blue with the 20% bonus) + 66,375 (Hyatt, 3 nights in Tuscany) + 60,000 (Hyatt, 3 nights in Rome), rounded up to 127,000 on the hotels because transfers move in 1,000-point increments = 190,000 points
Cash: $312.60 (outbound taxes and fees) + $461.06 (return taxes and fees) + $52 (buying World of Hyatt points, if needed) = $825.66
Two things worth knowing about that last line.
First, without ThankYou points and the transfer bonus, the flights cost 75,000 instead of 63,000, which leaves me 2,000 points short for the trip. In that case I'd buy Hyatt points, which start at 2,000. The regular price of 2,000 World of Hyatt points is $52.
Second, buying points is normally not a good idea. This is the exception: topping off a balance by the bare minimum to lock in nights you already have booked. Not a strategy, just a patch.
And with well over $1,000 of cash budget left, the rental car in Florence for 3 days is covered, along with the train to Rome, getting around the city, a food tour, and whatever else looks good when we get there. 🤷♀️
What didn't make the cut
The Saturday departure, obviously. Over 100,000 points one-way for two people in economy is not a redemption, it's a penalty.
The New York repositioning, at 25,000 points per person round-trip. It's a legitimately fine deal and I'd take it in a different season. But it costs a positioning flight and it eats vacation days, which defeats the entire reason I was looking at it.
Chicago at 65,000 for two, for the same reason.
Every one of those was a way to protect my dates. Moving my dates was cheaper than all of them.
Bottom Line
If you can pivot to fly out and return on Mondays, you can save yourself a mountain of points and the headache of positioning flights eating into your precious PTO.
You'd need one of these cards to take advantage of the transfer bonus. But otherwise this entire trip could be booked holding just this card, which is a transfer partner of both Flying Blue and Hyatt, and would be my pick for a trip like this.
And to every teacher reading this who just did the math on whether they can swing one extra day: I see you. Take the Monday. 😉
