Hacking Greece: Results and Lessons Learned

Hacking Greece: Results and Lessons Learned

Hello folks! Hope things are going well. Back in December my wife and I began strategizing our travel hacking strategy for our ten-year anniversary trip to Greece. The trip is coming up this fall and I’m here to report we have successfully completed hacking Greece! It wasn’t without a few trials and tribulations, but airfare and hotels are booked and we have a tentative agenda set. It is certainly exciting to have everything official now and we look forward to continuing to research a few things we want to do when we are there. Without further ado, here is our “report card”.

Starting Point

As outlined back in my strategy to hack Greece, Lucy and I held a combined 260,000 Chase Ultimate Reward points (available to be redeemed for travel purchased through the UR portal) and 200,000 American Airline miles. Since then, the AA miles have been unexpected depleted. The AA account took a 42.5K hit in January when I booked a short notice trip back to the Midwest for the baptism of my niece. Then, Lucy’s cousin announced his engagement and planned wedding in May 2018. We used 75K AA miles to book three tickets (thankfully our youngest still flies free!) back home for the wedding.

Flights to Greece

First things first, flights! You may recall from our original post on travel hacking Greece, I was hoping flights would come in the range of $500 to $1,000 and I was intending to use ~50,000 Amex reward miles for each my wife and I. This didn’t work out for a couple reasons. First, I was hoping that once both my wife and I hacked the Business Gold Rewards card from Amex that we could then combine the points into one account to book the travel. Turns out Amex doesn’t allow you to transfer points within a household similar to how the Chase Ultimate Reward portal works. So that was a bummer and definitely complicated things.

Secondly, flights came in a bit higher. We were admittedly being picky on the itinerary. While we could have gotten to Greece cheaper, we preferred shorter trip duration and flight departure times that fit our ideal schedule. We’re still working and are slave to limited paid time off days, etc. so we wanted specific departure times including right after work on Friday and a mid-morning return flight getting us back in the mid-afternoon. All told, we were looking at ~$1,450 per flight.

As a result of these two factors, it just didn’t work to use the Amex rewards. What a wrench in the plans! But good thing we had alternatives. Specifically, we had the 260K Chase UR! BOOM! Airfare booked and we are now 230K UR lighter…

Yup, you heard me right. We used 230K UR points to book our Greece flights valued at a combined $2,900 (~1.25 dollars per point used…not shabby).

One More Flight

While the above mentioned flights get us from Charlotte to Athens, our Greece trip is also going to entail a couple day stop at Santorini. We could do a ferry, but from what we’ve read they didn’t sound too accommodative or comfortable. Plus they take upwards of five to seven hours! So alternatively we elected for the 50 minute flight from Athens to Santorini. Not willing to sacrifice our ideal arrival time in Santorini for lower cost flights, they ended up costing us about double the cheapest alternative. No problem though…we got points for that…

As part of our hacking strategy, we hacked the Capital One Spark card. We booked these flights for $350 on the Spark card and then “erased” it using 350 of the ~600 miles we earned.


Going back to my original guestimate in December, I was hoping to get hotels booked for under $300 per night. That may sound absurdly high to some, but keep in mind this is a special trip for us and we don’t want to cut any corners. We’re looking for 4-Star hotels with views and plenty of creature comforts!

I’m happy to report that our seven night stay has ultimately come to $1,800, or just over $250 per night! Happy to come in a bit below expectation here, but it still doesn’t make up for how far off I was on estimating the flights!

We ended up at booking three nights at Nefeles Luxury Suites in Santorini for ~$1,050 and four nights at Fresh Hotel Athens for ~$750. Both of these hotels were booked with the option to cancel with full refund, so we’ll keep an eye out in case we found cheaper alternatives later. But this was also really handy as it allows us to book now and pay upon arrival…more time to complete our hacking strategy.

Cards Hacked

To date, we’ve hacked the two Amex Business Gold cards (one for each of us – no longer planning to use for this trip…) and one of the Capital One Spark cash back cards (partially utilized by the $350 flight between Athens and Santorini).

We still plan to hack another Spark cash back card for me and the other available Spark miles card (50K travel miles) for both Lucy and I.

The plan will be to use the rewards from two spark cards (approximately $500 or more in value) for the Nefeles hotel upon arrival (just asking the front desk to split the charge on the two cards). BOOM! That is taken care of!

Next, we’ll use the $250 remaining value on our already hacked Spark card plus the fourth and final Spark card (~$500 value) for the Fresh Hotel Athens charge. BOOM! Done and done!

Lessons Learned

The Amex card is not my favorite right now. First, I think it is ridiculous you can’t transfer points among family members. I’m surprised because it is super easy with Chase (I did it when booking the airfare for 230K UR…). I would have thought Amex would allow this as well given the two companies respective travel booking portals are direct competitors. Lesson learned! But I’m not done with you Amex…

Secondly, I thought I would use the Amex rewards for booking the Greece hotels or the short airfare between Athens and Santorini. Well the airfare was ridiculous…just incomprehensible. The cheapest flight was over $1K and involved two stops through Munich and Frankfurt and over 13 hours travel time…huh ok…I’m guessing they don’t contract with local airlines that are offering the 50 minute direct flights.

I tried searching for hotels and at least I had a little more luck. Reasonable options populated, but when I checked the price on the Amex portal compared to rates directly from the hotel website or booking.com I realized the rates were inflated by up to nearly 50% in some cases for comparable room types.

So I’m done with Amex. It appears the portal is really only useful when it comes to domestic flights so we’ll resort to using these rewards for airfare back home to the Midwest some other time…or take a haircut on the rewards and get regular expenses reimbursed. Either way, we’ll get the points utilized and then cancel the cards before the annual fee kicks in.

Has anyone else experienced issues with the Amex reward portal? I thought it was well renowned…I’m disappointed but oh well.


All in all, we booked approximately $5,050 of travel for free! Chase Ultimate Rewards picked up ~$2,900 of airfare while Capital One rewards are picking up ~$350 of airfare and ~$1,800 of hotel costs.

All we have left to pay for is food, souvenirs, and likely a couple tour packages in Athens and Santorini.

Tentatively, here is our agenda:

Day 1 (Friday):

  • Leave Charlotte after work

Day 2 (Saturday):

  • Land in Athens mid-afternoon Saturday (~13 hour flight duration)
  • We have about 3 hours to get luggage and through customs to board our next flight directly to Santorini
  • Leave Athens in the evening and land in Santorini (<1 hour flight duration)
  • Nefeles Luxury Suites

Day 3 (Sunday):

  • Fira to Oia walk along cliffs
  • Volcano and hot spring boat tour
  • Sunset dinner at Mezza (highly recommended dinner spot)
  • Nefeles Luxury Suites

Day 4 (Monday):

  • Visit Akrotiri ruins
  • Beach time
  • Dinner at Mexani Mas (highly recommended to us)
  • Nefeles Luxury Suites

Day 5 (Tuesday):

  • Free day in Santorini
  • Depart Santorini in evening back to Athens (<1 hour flight duration)
  • Fresh Hotel Athens

Day 6 (Wednesday):

  • Day trip to Delphi ruins (decided this as it was recommended from friends and seems to be an easier day trip then heading over to Olympia) – so much to explore on the Greece mainland that we’ll have to return sometime…
  • Fresh Hotel Athens

Day 7 (Thursday):

  • Tour Athens

Day 8 (Friday):

  • Free Day

Day 9 (Saturday):

  • Depart Athens mid-morning and arrive back in Charlotte mid-afternoon (~13 hour flight duration)

Final Thoughts

As you can likely tell, we didn’t necessarily “optimize” our travel budget or our use of miles that well. Admittedly, it wasn’t a primary focus. First, we want our ten-year anniversary trip to go as smooth as possible and avoid any undue headaches that are common with any international travel (or domestic for that matter).

We don’t want to waste any unnecessary time traveling so we have the shortest flights possible. We want comfortable beds and accommodative lodgings so went with 4 Star hotels or above. And specific to Santorini, we wanted a hotel with breathtaking views of the caldera from our hotel room balcony!

While this is unlike us to an extent, that is the benefit of travel hacking. We are reaping massive rewards from everyday expenses (particularly the daycare expense that we can put on our credit card!). Therefore, we don’t mind splurging a bit.

This is going to be a trip of lifetime and we don’t want any regrets. To us, spending $5K on hotels/airfare instead of skimping here and there to cut it to $4K is well worth it if it means we get the cherry on top our sundae!

Olive oil, wine and baklava here we come…

Thanks for taking a look!

The Green Swan

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  1. My mom and I are using skymiles earned on Amex for an upcoming trip. It was tricky, as the ‘charge’ to transfer points would have been ~$700!! This meant we had to call with both of us there to book over the phone. The guy was very helpful. We couldn’t pick seats just then, maybe because partnered airline etc. Turns out, they will either let you pick seats 24 hrs before the flight, pay a little to pick 72 hrs before or pay more to pick now. Because it’s a long flight, we want to sit together and not leave it to chance 24 hrs before. We did get the flights for just the taxes, so I feel like I saved enough I can afford to pay for the seats.
    We will see how it all works out.

    Your Greece trip sounds wonderful! It sounds like the points worked out ok, even if not ideal to start with.

    1. Oh wow! I guess that’s nice you were able to book it together over the phone. We may do that to when we redeem our Amex awards so that we’re all on the same travel itinerary/booking. Rather than booking her and I and the boys separate… We’ll see. Some cards are definitely easier than others to redeem awards but either way it’s still worth it! Glad it worked out for you!

  2. I love the chase rewards and have found their whole UI experience so wonderful.

    I’ve moved on to the capital one venture once I used up the points and find the travel reimbursement a little easier bc there aren’t the limits of who they contract with.

    So glad you got to see Santorini man, it is such a beautiful and fantasy place. My favorite thing when I was there was a catamaran tour followed by the sunset. Can’t wait to take my future wife there one day, and hope you enjoyed it as much as I did!

    1. Thanks Chris! Actually we are set to go there in the Fall, but are excited to see everything. Good to hear you recommend the sunset catamaran tour. We’re looking at a bunch of that stuff now and trying to figure out the exact agenda, reserving the tours, etc. Let me know if there is anything else you’d recommend or any tips/tricks you learned there. Thanks!

      1. Ah I see! I must have missed the itinerary when scrolling with my phone.

        For your free day you could check out the beaches and relax if you wanted, they were beautiful and of course I had a few drinks.

        Other than that you have everything covered I did, Santorini was just so beautiful I can’t wait to go back.

        1. Great! We’ll have to be make it down to the south part of the island to check out the beaches. You’re getting me excited to visit!

  3. Wow, that’s some great travel hacking JW! And it was smart not to cut corners on a trip like that. We have our 25 year anniversary coming up in a few years and I need to start thinking about hacking my way there. Ironically, Santorini has been on our short list as well… Well done!

  4. This brings back some good memories for me. My wife and I went to Greece about a year after we were married for a late honeymoon. We spent a week on our own with our time split between Nafplio, Santorini, then Athens for a day. Then we went on a 7 day horseback tour on the Pelion Peninsula. Far and away the best vacation we ever had. I would highly recommend renting a scooter or two on Santorini and explore. We took a day and rode the entire island. We also did the volcano and hot springs boat tour, and it was really nice. Unless they have gotten some faster ferries, that ride from Athens to Santorini was more like 10 hours. We did an overnight ride and got into Santorini around 6am.

    I think we were there for 15 days total, and back then we were young enough to not have made any plans whatsoever for that entire first week (no places booked to stay). We spent the flight over looking through tourist books to decide where we wanted to go. The second week on horseback was all planned out. We normally don’t like to revisit places we have already been, but I think we will make an exception for Greece. Have a great time over there!

    1. Wow what a trip! Thanks so much for sharing. Great idea to get the scooters, sounds like a nice way to see everything. Although I may have to talk my wife into that, not sure how comfortable she’ll be.

      And we for sure will be doing a cruise. I want to have a little time to hike the volcano. The hot springs sounds like a crazy phenomenon, I heard people jump off the boat and the water gets warm as you swim up to the springs.

      Ha you folks truly fly by the seat of your pants! What a way to travel, I’m sure it was a blast! Thanks again for sharing!

  5. Sounds like a great tour. I have a 17 day tour with students to Greece in 6 weeks. And now that I think about I bet our tour guide could give you some info on some great tours of Athens. I have already done this tour before with students, but we are adding time on to some Greek Island (Rhodes).

    1. The agenda you shared of your trip in my prior post was much appreciated and helpful to reference! Sounds like you’ll have a blast.

      I would definitely welcome any info your guide had to offer! Thanks Jason.

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