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Originally, we planned to travel to Greece and the United Kingdom in late-August and early-September for our two week honeymoon, as we were able to find some cheapish tickets. After debating for a few months on when to make some big life changes (marriage, school, moving), we decided that this time frame would work well. Well, clearly we were W-R-O-N-G! You know what they say about best laid plans? Well, here’s the story about how we had to rebook our entire honeymoon!

(READ MORE: Booked! Part 2 of a very European honeymoon)

Once we realized (for good reasons!) that we weren’t going to be able to make that vacation work, I went into full on planning mode. We still wanted to see Greece and the UK, but booking a two-week trip ~90 days out can be difficult, especially if you want to do the majority of it on points. I have to say, I’m pretty impressed with the outcome, so let’s dive in!

Part One: Getting from New York City to London

In order to make this work, we flipped the order of our trip. Instead of Santorini first, we’d be jetting off to London. I know people gripe about American Airlines sAAver awards, but I was instantly able to find two economy tickets for 27,000 points + $5.60 each for the flight there. Being our honeymoon, I really wanted to surprise Nick with a better experience than economy, so I put those tickets on hold, and prayed (and prayed and prayed) for two sAAver Business Class tickets to appear. Lo and behold, two days later my prayers were answered and I was able to snag two seats for 55,500 points + $5.60 each. Wahoo!

a screen shot of a phone

This flight is on one of American’s recently reconfigured 777-200ERs with the reverse herringbone seating plan. We’re sitting in the middle so we can sit together (the cabin is arranged 1-2-1) in two forward facing seats. I’ve read pretty positive things about this seat on One Mile at a Time and The Points Guy, so I’m looking forward to trying it out for myself!


  • Cost: 111,000 American Airlines AAdvantage points and $11.20
  • Paid with: The Platinum Card® from American Express
  • Points earned: 34 American Express Membership Rewards points

Part Two: London

This was probably the easiest change to make, as Hilton makes it really easy to cancel bookings. Once our reservation was cancelled and our points redeposited (almost instantly), we pooled our points and rebooked for the six days we wanted. We’re staying in the same hotel, the DoubleTree by Hilton Hotel London – West End.

a close up of a form

As you can see, we’re still doing a Points + Cash redemption, which will set us back 272,000 points and $509.32 when you factor in the exchange rate. Our 272,000 points are saving us ~$1,600, which means we’re getting half a penny per point —  pretty much the norm for Hilton


  • Cost: 272,000 Hilton Honors points and $509.32
  • Paid with: Hilton Honors™ Surpass® Card from American Express
  • Points earned: 6,112 Hilton Honors points

Part Three: Getting from London to Santorini

Previously, we were set to fly Thomas Cook on the reverse leg of this trip (JTR-LGW), but I was hoping that there would be a points option now that we were rebooking. Again, the higher being you believe in smiled down, and we were able to use British Airways Avios to get from London to Greece.

a screenshot of a flight schedule

For 45,000 Avios and $189.30 in taxes, we were able to book LHR-VIE-JTR. This is in Club Europe class from London to Vienna and Economy from Vienna to Santorini. I’m a little nervous about the 45 minute connection in Vienna, but their website says legal connections can be as short as 25 minutes for Star Alliance carriers, so I’m hoping 45 minutes on oneworld isn’t too much of a stretch. If anyone has experience transiting in Vienna, please share!


  • Cost: 45,000 British Airways Avios and $189.30
  • Paid with: The Platinum Card® from American Express
  • Points earned: 947 American Express Membership Rewards points

Part Four: Santorini

This part isn’t changing at all, so I’ll repost what I wrote before:

Once we get to Santorini, we’ll likely rent a car, but I haven’t gotten to that stage of the project yet 😉 . We’re staying at an Airbnb on the east side (beach side) of the island. Here’s our rationale, courtesy of Nick:

We chose the east side of Santorini because the Airbnbs on that side of the island were much nicer for much less money, and we found one that’s 90 feet from the ocean. We knew we’d want to be spending much of our time there on the beach, and the other side of the island is all cliffs, so all of our beach days would start and end with a long car ride. Also, the Airbnb we found has a pool, so we can swim in the ocean and then dunk in the pool! We know we’ll be spending some time on the cliff side of the island to get those amazing sunset views, but for us and what we wanted to do, it made sense to stay on the east side.

a pool in a building

We’re staying at this AirB&B, and for six nights, which will cost us $1,034.00. I knew we wouldn’t be able to use points for this part of the trip, as there are only two chain hotels on the island (both Starwood, and currently we have 34 Starwood points 🙂 ). I also enjoy AirB&Bs, as I think they let you have more of an “experience” when you’re somewhere, rather than what you might get from a chain hotel. There was a fee to change our nights, as the nights we were changing to were more expensive. Also as one reader pointed out, I forgot to take advantage of the Delta/AirB&B relationship for 3x Delta points per dollar spent at AirB&B. I can’t be perfect ALL the time 🙂 .


  • Cost: $1,034.00
  • Paid with: The Platinum Card® from American Express
  • Points earned: 1,034 American Express Membership Rewards points

Part Five: Getting from Santorini to Athens

This is where we get a little creative. I really wanted to find a points redemption for the the way home, but the only options were out of Athens. Rather than bite the bullet and pay cash, I did what any sane person would do: took ANOTHER flight! We’re positioning ourselves to Athens with a Ryanair flight, which set us back ~$180 for two tickets. It was actually cheaper to book Leisure Plus rather than Standard, as we plan to have large suitcases with us. I’ve never flown Ryanair, so I’m looking forward to the experience–thankful it’s for a 50 minute flight and not four hours!


  • Cost: $181.98
  • Paid with: The Platinum Card® from American Express
  • Points earned: 910 American Express Membership Rewards points

Part Six: Getting from Athens to New York City

Once we’re in Athens, we have a six hour layover, and then we’ll be flying Turkish Airlines from Athens to Istanbul and then Istanbul to New York City. Thanks to my stash of American Express Membership Rewards points, we booked two Business Class tickets using Aeroplan, which meant that our flights ended up costing 115,000 points and $116.48 in taxes.

a screen shot of a white box

I’m looking forward to another Business Class redemption, especially since the flight from Istanbul to JFK is ~11 hours! We will be affected by the electronics ban, so we’ll stock up on (paper) books and podcasts! We’re seating in 2A and 2B for both our flights, and I’m really looking forward to trying their business product on the Boeing 777-300ER.


  • Cost: $116.48
  • Paid with: The Platinum Card® from American Express
  • Points earned: 582 American Express Membership Rewards points

What about the other trip?

Yeah…that’s a thing. I’m working to figure out the best way to get Meridiana and Thomas Cook to refund my fares, but I’m not confident that will happen. I paid with my Platinum Card® from American Express, so if anyone knows if they offer some sort of travel protection that I’m not thinking of, that would be helpful. I’ll also need to cancel by LHR-JFK American Airlines ticket, which will cost me $175, but I’ll get my 54,000 points back, so it’s not TOTALLY terrible. You live and you learn–this is why refundable fares are a thing; I’ll think twice about booking nonrefundable fares next time.

I will admit, I’m MUCH happier with this arrangement. I’m in Business Class for both of my longhaul legs, which is nice not only because it’ll be more comfortable, but you (hopefully) only have one honeymoon, so you might as well make as memorable as possible!

What’s the cost?

Given all that above, the actual out-of-pocket costs for our European honeymoon is $2,042.28 and 535,000 points/miles. That means we’re spending roughly $145.87 and ~38,214 points a day in travel costs. We also earned 3,507 American Express Membership Rewards points 6,112 Hilton Honors points, which we can use for future trips. If you factor in the nonrefundable fares, we’re closer to ~$3,400 in cost. Again, I’m hoping to get some of those fares removed, but I’m heading into those fights with a healthy dose of pessimism.

Header image courtesy of Mstyslav Chernov via Wikimedia Commons

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