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Flying to Italy on Points: A Smart Redemption for a Special Trip

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This summer, I’m meeting my daughter in Venice for a Backroads hut-to-hut hiking tour in the Dolomites to celebrate her college graduation. Travel has always been a big part of our lives, and for a trip this special, I wanted to make the journey just as enjoyable as the destination. Of course, I turned to points and miles to make it happen.

Booking the Flight to Venice: Delta One for Maximum Comfort

For the long-haul overnight flight to Italy, I knew I wanted to fly business class on a direct flight. While I typically look for partner airline redemptions to maximize value, at just five months out, award space was tight. I ultimately booked Delta One from JFK to Venice using 318,700 Delta SkyMiles, a ticket that would have cost a staggering $8,253 in cash.

I always do a simple calculation before using miles:Cash Price/MilesUsed×100

For this redemption, I got 2.67 cents per mile, which met my personal threshold of at least 2 cents per point. Yes, it’s possible that with more flexibility (or booking further in advance), I could have secured a better deal, but I prioritize comfort, convenience, and direct flights—so this was the best available option for my needs.

Most of these miles came from American Express Membership Rewards®, which I earn quickly thanks to my American Express® Gold Card (4x on dining & groceries) and The Blue Business® Plus Credit Card from American Express (2x on all purchases up to $50K annually). I also frequently refer people to Amex cards, netting me valuable referral bonuses that help fund future trips.

While I’m excited about the lie-flat seat, the exceptional service, and (of course) the warm chocolate chip cookies, I think what I’m most looking forward to is getting access to the new Delta One Lounge at JFK.

Who Can Enter the Delta One Lounge at JFK?

Delta recently opened this ultra-premium lounge, and it’s not like their usual Sky Clubs—it’s more exclusive. Entry is limited to passengers flying Delta One on international flights like me! (not partner airlines and not via Amex Platinum or status). Since I’m flying Delta One, I’ll be able to experience it before takeoff!

Flying Home in Economy—And Why That’s Fine

For the return flight, I was much more flexible. When I don’t need to sleep, I’m happy flying economy, especially if I can use points to cover the ticket. I booked two United economy tickets home for both myself and Jessie for 40,000 United miles each—a total of 80,000 miles for flights that would have cost $2,176 in cash. That works out to 2.7 cents per point, which is another decent redemption.

One of the reasons this was an easy booking? United’s family pooling feature. My family of five shares a pool of United miles, so I was able to pull from our collective balance rather than transferring in from another program. If I didn’t have enough, I could have topped it off with Chase Ultimate Rewards® or Bilt Points, since both transfer to United 1:1.

Takeaways: Plan Early, Stay Flexible, and Earn the Right Points

This trip reinforces what I always tell people:

  1. The earlier you book, the more options you have—especially in business class.
  2. Flexible points (Amex, Chase, Bilt) give you the best opportunities to book premium travel.
  3. United’s family pooling makes it easier to redeem miles for flights without worrying about splitting balances across accounts.

By planning strategically, I’ve made this trip both luxurious and affordable—ensuring we arrive rested, ready to hike, and with more money in our pockets for celebrating my daughter’s milestone. Now, bring on the Italian Alps!

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K. Roth
... I saved $700 in annual fees and scored 120,000 worth of bonus points. I also got $100 off a pair of fancy headphones and $200 worth of airline gift cards. ....
D. Cohen
I am obsessed with Cindy "The Points Mom". Today she saved me 100,000 points and $1500 booking a flight...
M. Bernaducci
A huge shout out to CINDY GREENSTEIN, aka The Points Mom, for helping me book our flights to Greece using points. Money wise it would have cost $12k. I learned so much from her! Contact her. You will not be disappointed.

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