Free tickets to Italy? Per favore, sign me up!

OK, OK, “Free” is slightly overstated. Two round-trip tickets for $418.86 doesn’t have quite the same ring to it, but “a screaming deal” regardless.

We’ve got not one, but two trips to Italy next year. Somehow the stars aligned for points bookings, and both trips have desirable flights in preferred airports! While I love upgrades and more premium seats, I like getting heavily subsidized vacations and preferred schedule even more.

Here’s what we landed on (ha, like the airline pun?!)

Booking set one: Iberia via Alaska Airlines partnership

  • IAD (Washington DC) to VEN (Venice, Italy) via Madrid (MAD)
  • Leaves at 5PM, 2h layover, arrives 11:15AM next day
  • Total cost: $63.20 (2 tickets, $25 partner booking fees, the rest taxes) + 55,000 Alaska Airlines Atmos miles
  • Total value: $1,172.00 (2 tickets)
  • Savings: $1,108.80 ($1,172-$63.20)

Booking set two: KLM via Flying Blue via American Express points transfer (AMEX Platinum Card)

  • FLR (Florence, Italy) to IAD (Washington, DC) via Paris (CDG)
  • Leaves at 1:05PM, 1h45m layover, arrives at 7:15PM same day
  • Total cost: $355.66 ($139.40 partner booking fees, the rest taxes) + 50,000 True Blue points
  • Total value: $1,128 (2 tickets)
  • Savings: $772.34 ($1,128-$355.66)

The points redemptions value for each of these bookings is pretty good. On top of this, this redemption helps minimize both my out of pocket expenses AND getting the multi-legged (different arriving/departing airport) without getting reamed by the premium cost/rate for one-way flights.

  • Alaska redemption: $1,108.80 / 55,000 points = 2.016 cents per point
  • Flying Blue redemption: $772.34 / 50,000 points = 1.545 cents per point

My general rule across points redemptions is to target 1.5 cents per point at the low end. I’ve been sitting on a bunch of AMEX points (used to transfer to Flying Blue), so I’m happy to just have those be used. The Alaska points I recently got for a sign-up bonus, so I’m similarly happy to cash out quickly, particularly with such good value.

I’ll share a separate post on transfers and partners in the not distant future, as that’s a critical tool to help maximize the value of any earnings.

How much pizza am I going to eat on this trip? If my lactose intolerance doesn’t stop me, every single day. My phone search for “pizza” in images highlights some beauties. But I suspect authentic Italian may top even the best Richmond has to offer…

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