When Bailey N. cashed in points for a vacation to Greece, he checked off a couple big items: his first big rewards redemption and his first trip abroad. Here’s how the Arizona resident used credit card points to book a proposal trip to Santorini and a honeymoon to St. Lucia 18 months later.
The trip: Greece in August 2023 for two adults; St. Lucia in April 2024 for two adults
Flights: Phoenix (PHX) to Athens (AIA) in economy; Phoenix (PHX) to St. Lucia (UVF) in economy; Phoenix Sky Harbor International Airport (PHX) to Hewanorra International Airport (UVF) in economy; Hewanorra International Airport (UVF) to Phoenix Sky Harbor International Airport (PHX) in economy
Points spent: 320,000
Money saved: $4,000 *estimated
Planning a proposal trip to Santorini
A long-time American Express cardholder, Bailey had been stockpiling points for a while when he decided to use them for his first international trip two years ago. He and then-girlfriend McKenzie had long dreamed of seeing the Greek islands, so Bailey planned a trip to Athens and Santorini in August 2023 for the two of them. When it came time to book flights to Greece, Bailey wanted to get the best deal out of the points he already had — rather than opening new cards — which led him to discover point.me.
“We’ve read through blogs about how to use points properly to convert to miles, but point.me really saved us time because it made it so easy to get the best value out of them,” he says. “We want to use what points we have to travel as much as possible.”
Bailey and McKenzie each have an American Express Gold card and a solid stash of Membership Rewards that they have earned through their day-to-day spending. The two primarily spend money dining out and buying groceries, he says, so having the right card to fit their lifestyles — specifically, a card that earns 4x points on restaurants and at supermarkets — has made that card a good fit for the couple.
To book their one-way flights to Greece, Bailey transferred a total of 99,000 Membership Rewards from his American Express account to Flying Blue for two one-way economy tickets. The couple flew Air France from their home base in Phoenix (PHX) to Athens (AIA) with connections at John F. Kennedy International Airport (JFK) in New York and Charles de Gaulle Airport (CDG) in Paris.
For their one-way flights home on Air Canada, they converted 110,000 Membership Rewards from their American Express accounts to Aeroplan points to fly economy from Athens to Phoenix with a connection at Montréal Trudeau International Airport (YUL).
The couple started their Greece trip in Athens, where they spent their days sampling the local food and visiting the major sites like the Acropolis, which houses the Parthenon, and museums such as the National Gallery. They booked their lodging and in-country transportation via a Costco Travel package, then took the ferry from Athens to Santorini, where Bailey popped the question with the famed caldera and iconic whitewashed homes of Oia as his backdrop.
Planning a honeymoon in St. Lucia on points
After their Greece trip, Bailey and McKenzie had the travel bug and, once again, decided to search point.me to plan a honeymoon to the Caribbean. Following their wedding in Arizona in March 2025, the newlyweds flew to St. Lucia for eight nights in April. They transferred 56,000 Membership Rewards from their American Express accounts to British Airways Executive Club to fly one way in economy from Phoenix Sky Harbor International Airport (PHX) to Hewanorra International Airport (UVF) in St. Lucia with a connection in Miami.
Once they were settled in, they spent their days sailing, snorkeling, and hiking the Pitons. Bailey says visiting the Diamond Falls Botanical Gardens and taking a mud bath at Sulphur Springs were highlights of their time on St. Lucia. They paid cash to stay in Anse Chastanet, an all-inclusive resort on the west side of the island, then transferred 55,000 Membership Rewards to Flying Blue to book two one-way Delta economy seats home via Air France’s website, departing from St. Lucia to Phoenix with a connection in Atlanta.
Bailey’s top tip for using points
“Using points is definitely harder than we thought it would be,” Bailey admits, adding that it requires a lot of organization to know the best airline alliance to transfer points to. “We never had the time to dedicate to searching all the different airlines for the best deal, so point.me was pretty powerful for us.”
Having flexibility in the future will open the door for even more possibilities for better points redemptions, he says. For their honeymoon, Bailey and McKenzie had a limited timeframe in which to travel immediately following the wedding, but they’re already hoping to plan their next trip around where they can get with AmEx points.
“We’re currently looking at flights in the fall and have a lot more flexibility — we’ll be using point.me to figure out where to go based on how we can use our points,” he says. “We have a good amount of points and want to try to find some good deals and good redemptions for other locations.”
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