Santorini Flights: Why I Paid Cash Instead of Using Points

With three different resorts booked over one long weekend, with a game plan to compare all three on as similar a basis as possible, the flights became even more important than usual. Every hour gained or lost would affect one of the resort comparisons.

In reality, the flight booking involved almost as many decisions as the hotels themselves. Could miles produce better value? Was Santorini Airport necessarily the right destination? Should we prioritise arriving home earlier or enjoying another afternoon at the final resort? And if we were paying cash anyway, could we structure the booking to make better use of our credit card benefits?

The obvious destination was Santorini Airport (JTR). That sounds almost too obvious to mention, but several flight searches kept presenting Heraklion (HER) in Crete as a nearby alternative.

Geographically that’s true. Practically, it isn’t.

Flying into Heraklion would have meant adding a transfer to the port, a ferry to Santorini, and then another transfer to our first resort. That might make sense as part of a longer Greek island itinerary, but for a three-night weekend built around comparing three resorts it simply added complexity without adding value. Once HER was ruled out, the search became much simpler.

The next step was checking whether miles could improve on the overall itinerary. There was some interesting award availability, but none of it solved the trip we were actually trying to take.

For example there was a British Airways business-class redemption through American Airlines for 22,500 miles plus ~US$34. The problem was the outbound. Nothing comparable existed on the Friday morning we wanted to travel, and the search engines kept trying to solve that by routing to Heraklion instead, bringing us straight back to the ferry problem we’d already dismissed.

A mixed itinerary with one cash flight and one award remained possible, but it never became particularly compelling. The cash fares were already reasonable for peak summer travel, and paying cash unlocked credit-card benefits that simply weren’t available on an award booking.

The hotels and flights were deliberately booked in different calendar months.

The Fine Hotels + Resorts reservations had to be completed before the end of June because our first-half Platinum hotel credits were about to expire. The flights, however, deliberately waited until July.

By the end of June we’d already used every available Hilton Aspire quarterly airline credit. Booking the flights a few days earlier would simply have been an ordinary airfare purchase. Waiting until the calendar rolled into the third quarter meant a fresh set of airline credits became available, changing how I wanted to structure the booking.

The flight timings also mattered.

The outbound departs Heathrow at 8:15am and lands in Santorini at 2:05pm. That isn’t especially early, but it still leaves enough time to reach Vedema and enjoy the first afternoon and evening. With three separate one-night resort stays, every few hours count. Arriving late would effectively remove a significant proportion of the first hotel’s value.

The return involved a more interesting choice. British Airways also offered an earlier departure, and at first glance arriving home sooner seemed attractive. The more I thought about it though, the less sense it made.

Our final stay was at Magma Resort, where Fine Hotels + Resorts includes breakfast for two, a US$150 food and beverage credit and guaranteed 4pm checkout. An early afternoon flight would mean breakfast, packing and leaving. The 5:25pm departure would give us another relaxed morning, time for lunch, and the opportunity to make proper use of Magma’s dining credit before heading to the airport. For this particular trip, those extra few hours seemed much more valuable than arriving back in London a little earlier.

Once we’d decided to pay cash, another optimization appeared.

Like most airlines, British Airways expects everyone on the same reservation to book the same fare family. That’s convenient for the airline, but not always for the customer.

For a three-night summer trip we only need one checked suitcase between us. Buying baggage-inclusive fares for both passengers would simply mean paying for a second checked bag we had no intention of using.

The obvious solution was to split the booking into two separate reservations. One ticket includes a 23kg checked bag together with complimentary seat selection, while the other is hand-baggage only. That reduced the total airfare while still giving us all the luggage we actually needed.

We also thought there might be one final benefit. By waiting until British Airways allocated the seat on the hand-baggage reservation before choosing seats on the baggage-inclusive booking, we hoped it would simply be a case of selecting the adjacent seat rather than paying for seat selection on both tickets.

Splitting the booking also allowed each reservation to be paid with a different Aspire card, giving us the opportunity to trigger two separate quarterly airline credits while earning 7 Hilton Honors points per dollar. The separate reservations therefore solved three problems at once: we only paid for one checked bag, we could use two different payment cards, and each booking became eligible for its own quarterly Aspire airline credit.

At the time of booking, the strategy was expected to reduce the effective cost further through two separate US$50 Aspire airline credits while earning Hilton Honors points on the airfare.

Looking back after the trip, I’d make exactly the same decisions again. Both Aspire airline credits posted as expected, the later return flight gave us time for one final lunch at Magma before heading to the airport, and at no point did we wish we’d taken the earlier departure. None of the award options we considered would have improved the overall trip.

The only idea that didn’t really work was our attempt to save on seat selection by splitting the reservations, but that was a minor disappointment compared with the savings from paying for only one checked bag and triggering two separate airline credits.

Three Santorini Resorts, Compared Side by Side