In 2021, my husband and I made a pact to take one kid-free trip together every single year. With two young children, careers, and the endless stream of school projects and activities, our stress levels tend to reach a breaking point at least once a year. And when that happens, nothing brings us back to center quite like a tropical getaway.

So far, the Caribbean has been our sanctuary. We’ve explored Aruba, Turks and Caicos, and most recently, St. Lucia—all for points totals that felt almost . . . illegal. I’m talking about incredible award flight redemptions that made me feel like I’d won the lottery. But here’s the thing, this isn’t luck. I’ve refined a method that works and helped friends snag equally amazing flight deals, all using points.

If you’ve ever dreamed about relaxing on white-sand beaches without breaking the bank, this guide is for you.

 

 

Why Charlotte Douglas Airport (CLT) is a Hidden Gem

One of my best-kept secrets? Location, location, location! Living in North Carolina has opened my eyes to the power of Charlotte Douglas International Airport (CLT). This airport is a Caribbean flight Mecca that is often overlooked in favor of larger airports like Atlanta (ATL) and Miami (MIA). I have found that using CLT as a positioning airport is one of the keys to my award flight success. CLT is not my home airport, in fact—I now willingly drive four and half hours in order to avoid a layover flight because nonstop flights are golden. Nonstop routes also have some of the best options when booking award flights

CLT offers nonstop flights to twenty-one Caribbean destinations, all on American Airlines. That alone is exciting, but here’s the kicker: because American Airlines has fifteen partner airlines through the oneworld Alliance, you can use points from fifteen other airline programs to book these flights at the best possible point rate.

Here are the destinations you can reach nonstop from CLT:

• Antigua (ANU) 
• Aruba (AUA) 
• Bermuda (BDA) 
• Bridgetown, Barbados (BGI) 
• Curaçao (CUR) 
• Grand Cayman (GCM) 
• Grenada (GND) 
• Montego Bay, Jamaica (MBJ) 
• Nassau, Bahamas (NAS) 
• Providenciales, Turks and Caicos (PLS) 
• Puerto Plata, Dominican Republic (POP) 
• Punta Cana, Dominican Republic (PUJ) 
• San Juan, Puerto Rico (SJU) 
• San José, Costa Rica (SJO) 
• Saint Croix, U.S. Virgin Islands (STX) 
• Saint Kitts (SKB) 
• Saint Lucia (UVF) 
• Saint Thomas, U.S. Virgin Islands (STT) 
• Saint Vincent (SVD) 
• Sint Maarten (SXM) 

That’s a lot of sandy beaches within easy reach, and a ton of opportunity to score a great redemption.

 

 

How I Find the Best Award Availability

Flexibility is everything when it comes to points and miles. When we first started traveling to the Caribbean, my only must-haves were:

• Somewhere close. I wanted to be within six flying hours from Charlotte and my children.
• A tropical and beautiful location.
• A Hyatt property nearby (because I love a good points-hotel stay, and Hyatts are my favorite). 

Instead of being locked into one destination or date, I searched for availability across multiple islands and let the best deal guide me. This approach works wonders if you’re open to discovering new places.

If you know exactly where you want to go, having flexibility with dates is key. If you’re locked into both a destination and a date? You might need to pay more points or even consider repositioning through another airport.

 

 

Finding the Award Availability: My Go-To Search Tools

• Point.Me – My go-to until 2023. This is a user-friendly tool and a limited version of it is free with some American Express Cards. You can even purchase a day pass. The first time I booked through Point.me, I used a 24-hour pass. 
• PointsYeah – My new favorite. User-friendly, lets you search multiple dates, and compares award charts easily. There are free and paid versions. I use the paid version because it lets you search wider ranges. 
• seats.aero – Another good one; our Points Talk Squad leaders, Alex, Jess, and Pam, use this search tool and recommend it. This tool is more of an advanced travel planning tool. 
• Roame.Travel – Great for searching a wide range of award availability. 

Once I find flights through one of these tools, I always double-check availability directly on the airline’s site before transferring points. And one rule I never break: book immediately once points are transferred, because these deals don’t last long!

 

 

Why I Love American Airlines for Caribbean Travel

Two words: airline alliances.

American Airlines is part of the oneworld Alliance, which means you can book AA flights using points from partner airlines like British Airways, Qantas, Alaska Airlines, Cathay Pacific, Fiji Airways, Finnair, Iberia, Japan Airlines, Malaysia Airlines, Oman Air, Qatar Airways, Royal Air Maroc, Royal Jordanian, and SriLankan Airlines. This flexibility can unlock major savings, especially if you don’t have American Airlines miles. 

To book partner airline travel, you use the partner’s website and points to book the flight. That flight will be flown and operated by American Airlines. For example, I have 48,000 Qantas points but want to book an American Airlines flight. I find the same AA flight on the Qantas website and book it directly with them. On the day of the flight, American Airlines will take care of you as if you had booked with them.

 

Favorite Redemptions and How I Booked Them

Booking award flights to the Caribbean is a great way to use points  Over the years, I’ve refined my process, and it all comes down to knowing which points to use, how to transfer them, and when to hit “book.” Here’s a closer look at some of my favorite Caribbean award redemptions and exactly how I made them happen.

 

Aruba

For a trip to Aruba, I found two American Airlines seats from Charlotte (CLT) to Aruba (AUA) for 24,000 miles per person. I didn’t have any American Airlines points at the time, so I transferred 48,000 Citi ThankYou® points to Qantas (1:1 ratio), one of American’s oneworld partners. Transfers are typically instant, but sometimes can take up to 24 hours, so timing is key. Once points landed in my Qantas account, I booked the American Airlines flights directly through Qantas’s website.

Pro tip: always check availability on the airline’s site after finding it with a partner. Occasionally, routing differences can affect eligibility.

I paired the flights with an all-points stay at Hyatt Regency Aruba.

 

 

Turks and Caicos

For a trip to Providenciales (PLS), the flights were again 24,000 miles per person round-trip. I transferred 48,000 Citi ThankYou® points to Qantas and booked through Qantas. The key for this booking was double-checking the American Airlines site after seeing availability on Qantas. This ensures your points don’t get stranded if a flight isn’t bookable through the partner.

Hotels we stayed at: Sail Rock and Point Grace, both in the Small Luxury Hotels of the World portfolio, now bookable through Hilton. Spoiler: this was my favorite Caribbean stay, and my full review of Turks and Caicos can be read here!

 

 

St. Lucia

Flights to St. Lucia’s Hewanorra Airport (UVF) were 32,000 American Airlines points per person round trip. Since I already had American points, this booking was direct and straightforward.

If you need to use bank points, Chase Ultimate Rewards® or Citi ThankYou® points can transfer to Qantas or British Airways. Once transferred, you can book the American Airlines flights. Transfers are 1:1 but may take a few hours to a day, so always confirm availability before initiating the transfer.

Hotels we stayed at: Secrets St. Lucia and Ladera. This was our latest trip, and we loved it!

 

 

Grand Cayman

For Grand Cayman, I booked five round-trip American Airlines flights through British Airways for 25,000 Avios per person round-trip. The steps:

1. Checked availability on British Airways. 
2. Ensured Avios balance was sufficient. (I transferred from American Express and Capital One, but you can also transfer points from Chase or Citi.)
3. Double-checked flight numbers on American Airlines. 
4. Booked immediately. 

Timing is everything. Avios transfers are mostly instant, but seats can disappear quickly.

Hotel: Kimpton Seafire. I recommended this hotel for a couple or families with five or more members. We love the Kimpton for large families. 

 

St. Kitts

Flights were 26,000 Avios per person, round-trip, booked through British Airways again. The process mirrored the booking for Grand Cayman above: confirm availability, transfer points, double-check flights, and book.

Tip: compare multiple transfer partners, like Avios versus American Airlines points, because sometimes one offers a significantly lower points cost for the same flight.

Hotel: Park Hyatt St. Kitts, a brief mention, since the focus is on the flight. Find out why we love this hotel here.

 

 

Dominican Republic

Flights to Punta Cana were 36,000 points per person, round-trip. We transferred 72,000 Citi ThankYou® points to Qantas to book two American Airlines tickets for my friend’s anniversary trip. Without Qantas as a partner, this booking wouldn’t have been possible at such a low points cost. The direct American Airlines flight was triple the points cost of the Qantas flight!

 

 

More Great Deals from CLT

• St. Thomas – 15,000 points via Aeroplan 
• Antigua – 20,000 points via Qantas 
• Montego Bay – 15,000 points via Etihad 

 

Other Departure Cities with Great Deals

Not near Charlotte or want to position from another large airport? Don’t worry, Atlanta (ATL) and Miami (MIA) also have incredible Caribbean deals.

From Atlanta (all with Delta SkyMiles®)

• Montego Bay – 11,000 points 
• Bermuda – 18,000 points 
• Nassau – 16,000 points 
• Barbados – 11,000 points 
• Aruba – 12,500 points

You can book these flights directly through Delta with Delta points or by transferring your American Express Membership Rewards® to Delta. Tip: if you hold the Delta SkyMiles® Gold American Express Card or higher, you get an additional 15% off your Delta flights. You don’t even need to use the card to pay the taxes, so you can even use another card, which can be helpful if you’re trying to meet a minimum spend!

 

 

From Miami (American Airlines flights booked via Qantas)

• Punta Cana – 6,000 points 
• Curacao – 12,500 points 
• North Eleuthera – 6,000 points 
• St. Maarten – 12,500 points 
• Kingston – 9,200 points 
• Cayman Islands – 9,200 points 
• Providenciales – 9,200 points 
• George Town – 9,200 points 
• Bermuda – 13,800 points 
• St. Croix – 13,800 points 
• Port of Spain – 20,700 points

 

 

Final Thoughts

Dreamy Caribbean getaways don’t have to drain your wallet—at least, not when you know how to work your points. Start with the right airport (CLT, ATL, or MIA), be flexible with dates and destinations, and use airline alliances to your advantage.

Our trips have been nothing short of magical, not just because of the turquoise waters and white sand, but because we walked onto each flight knowing we had booked one heck of a vacation for pennies on the dollar. And that, my friends, is the sweetest redemption of all.

 

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