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How to turn 14,000 Amex points into a Caribbean vacation

Victoria M. Walker
September 1, 2025
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As a traveler who has been using points and miles to travel the world for nearly a decade, I’ve become quite comfortable using tips and tricks to maximize my rewards.

I’ve adopted an “earn-and-burn” strategy, meaning that as I earn points or miles, I immediately use them to avoid sitting on them for months or years at a time. After all, points and miles were meant to be used, right?

I planned to book a round-trip flight to Santo Domingo as a quick getaway. The only problem was airfare. Flying from New York, where I’m based, to the Caribbean during peak season can be pricey, especially for last-minute travel.

This is when I decided to put my points and miles strategy to use. Of all of my points balances, I had the most American Express Membership Rewards points. I earn Amex points through everyday spending on various cards, using my cards on groceries, dining out, and travel.

Amex + Delta: A winning combo

Using ​Points Path​, I saw that the best deals were on Delta Air Lines.

This was great news for me. Delta flies nonstop from New York to several destinations in the Dominican Republic, like Punta Cana and Santo Domingo. Delta is also a transfer partner of Amex at a rate of 1:1, meaning I’ll get 1 SkyMile for every Membership Rewards point transferred.

Set on Santo Domingo, I checked Delta’s website regularly and explored different dates. I ended up finding a round-trip nonstop flight from New York-JFK to Santo Domingo for just 14,000 SkyMiles plus about $130 in taxes and fees.

Considering the cash price for the same itinerary was more than $350, and knowing that I still needed to book a hotel, plus ground transportation and excursions, this redemption was a solid deal.

I logged into my Amex account and transferred my points over to Delta. The transfer was instant, which was a relief because award tickets can disappear almost as quickly as they pop up.

For a round-trip flight to the Dominican Republic, I paid a fraction of the cash cost just by using points and miles.

Spending less on airfare meant more for my stay

With the flight sorted, I turned my attention to the rest of the trip. Not having to budget hundreds of dollars for airfare gave me room to splurge on a decent hotel.

I found a cheap stay at the Renaissance Santo Domingo, a hotel and casino, for just under $150 per night. I also booked a food tour and a walking tour, both of which felt like luxuries I could easily justify after saving money on the flight.

If you’re thinking about using points and miles for your next trip, start by coming up with a strategy to earn points. You can use cards that offer elevated earnings on spending like travel or dining, and take advantage of shopping or dining portals to earn more points or miles.

Keep your goal in mind, watch for award availability, and don't hesitate to jump on a good deal when you see it!

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