Cleared for takeoff: A weeklong 5-star getaway to Cancun for 250k points

Cleared for Takeoff is a weekly series showing readers like you the best ways to book future adventures using points and miles. If you’d like tips on booking your own trip using miles, please email us with your preferred itinerary and current mileage balance.

You don’t need to travel far to get your fix of white sand beaches and turquoise water. The Caribbean and Mexico, in particular, tend to be great options among U.S.-based folks in need of some Vitamin D. The weather is beautiful almost year-round and there are plenty of flights from all over the U.S. to various Caribbean destinations. Even better, Mexico and most Caribbean islands are open to Americans.

While there are many ways to visit Mexico or the Caribbean on points, today, we're going to help TPG readers Rosalyn Santos and Brian Sturgeon book their next trip there. Their email reads:

My husband and I are in our early 30s, from NYC (JFK and LGA preferred) and want to ta1ke a Caribbean or Mexico vacation in August/September. We are both fully vaccinated!

What we're looking for:

1. Direct flight, economy class is fine
2. 5 star preferred with good food options on site or near a town with restaurants
3. 5-7 nights

Here are our points breakdowns, but we're willing to pay cash if the point valuations aren't worth it (I'm all about maximizing points!)

1. 450,000 Bonvoy Points, 2 50,000 point certificates
2. 140,000 Ultimate Rewards Points
3. $300 travel voucher with JetBlue

Thank you!

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Current points stash

Rosalyn and Brian have a fairly limited number of points, and we'd like to see them diversify the types of rewards they earn going forward. For instance, we recommend they stock up on some more transferable point currencies like American Express Membership Rewards or Capital One miles. Nevertheless, the stash they do have should be just enough to cover their airfare and hotel.

• 450,000 Marriott Bonvoy points
• 140,000 Chase Ultimate Rewards points

They also have a $300 travel voucher with JetBlue and two Marriott Bonvoy 50,000-point free night certificates at hotels participating in the Marriott Bonvoy program (certain hotels have resort fees) and that come with certain Marriott cobranded credit cards. They should try to redeem these first as both of these types of rewards have expiration dates.

Airfare to Cancun

Based on Rosalyn and Brian's points balances and requests, the best destination for them would be Cancun, Mexico. There are plenty of nonstop flight options from the New York City area and some great Marriott Bonvoy properties.

JetBlue offers three daily flights between New York-JFK and Cancun (CUN). Round-trip fares on this route are usually around $300 per person, so Rosalyn and Brian's JetBlue credit should cover one of the tickets. There's not Mint business class service on this route, so they'll need to fly coach.

Related: How to save on your next trip to Cancun with points and miles

For the second ticket, I recommend they book through the Chase Ultimate Rewards Travel Portal. Since we don't know what Ultimate Rewards-earning card Rosalyn and Brian have, we'll assume they have the Chase Sapphire Reserve. This would mean that they can redeem their points on the travel portal for 1.5 cents apiece. So, a $319 ticket, for instance, would cost about 21,250 points — not bad. Meanwhile, those with the Chase Sapphire Preferred Card and Chase Ink Business Preferred Credit Card can redeem at 1.25 cents each.

Although JetBlue TrueBlue is a 1:1 transfer partner of Chase, they'll likely get more value by booking through the travel portal. That's because TrueBlue points have a relatively consistent value of 1.3 cents apiece. Plus, unlike traditional awards, tickets booked through Chase's portal earn TrueBlue award points and Mosaic-qualifying credit.

How to book this award with points

Booking flights through the Chase Travel Portal is as simple as it gets. The search engine is powered by Expedia (though not for much longer), so it should feel familiar to most people.

Start by logging in to your Chase account and then heading to your Ultimate Rewards dashboard. From there, click “Travel” in the navigation bar to access the travel homepage. Then, type in your departure and destination (in this case, airport code CUN), along with your travel dates as you normally would.

On the next page, you'll see all available flight options. Rosalyn and Brian will want to filter the results to only show nonstop flights operated by JetBlue. This way, they can book the same flight that they're going to redeem the travel credit for.

After you’ve selected your flights, you’ll see a summary of your ticket cost, along with options to upgrade to a higher fare type. Unlike traditional award tickets, you won't need to pay and taxes or fees.

The final step is to fill out the traveler details as you normally would. The system will default to points as the payment method, though you can choose to pay using a mix of cash and points. Then, hit the “Complete Booking” button and voilà, your flight will be ticketed and your confirmation sent to you in an email — no need to transfer any points to a different program.

Related: When should I transfer points to airline and hotel partners?

How to earn enough points for this award

Rosalyn and Brian already have more than enough Ultimate Rewards points to book this award. However, if you’re looking to replicate this itinerary and need more points, you can do so fairly easily with a welcome bonus from a new Chase card.

For instance, the Chase Sapphire Preferred currently sign-up bonus: 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening. Meanwhile, the more premium Chase Sapphire Reserve offers 80,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.

Cancun hotels you can book with points

The only hotel points Rosalyn and Brian have are with Marriott Bonvoy, so that's the program we're going to focus on. Luckily Marriott offers several properties to choose from in Cancun.

Rosalyn and Brian mentioned that they're looking for a five-star hotel experience, so the two best options for them are either The Ritz-Carlton Cancun or JW Marriott Cancun Resort & Spa. Both of these hotels are located directly on the beach in the Hotel Zone and classified as Category 6 properties in the Bonvoy program.

Award nights at either of these properties cost 40,000 points for off-peak dates, 50,000 for standard and 60,000 for peak. This is perfect because it means that Rosalyn and Brian will be able to redeem their up to 50,000-point free night certificates at either of these properties. Plus, when they redeem Marriott Bonvoy points for five consecutive nights, one of their nights will be free.

Related: Cleared for Takeoff: A trip to Puerto Rico for a family of four

While the Ritz-Carlton name is usually more prestigious, TPG's experiences suggest that the JW is the better pick in Cancun. The JW resort has a fresher feel overall, thanks to a more recent renovation. It features three pools and three dining venues and a full-service spa and plenty of activities, including tennis courts.

It's worth mentioning that Marriott is also in the process of integrating several all-inclusive resorts into the Bonvoy program, such as the Royalton Riviera Cancun Resort and Spa and Royalton CHIC Suites Cancun Resort and Spa.

How to earn enough points for this award

Between the two free night certificates and points, Rosalyn and Brian should be all set to cover their weeklong hotel stay. That said, if you wanted to replicate the itinerary, you could earn Marriott points quickly with a cobranded credit card from American Express or Chase. In addition to the annual free night certificates, some cards offer free night awards as a part of their welcome bonus. Here’s a look at all available cards alongside their current welcome offers:

• Marriott Bonvoy Boundless Credit Card: Earn 3 Free Night Awards (each night valued up to 50,000 points) after you spend $3,000 on purchases in your first three months from your account opening. Certain hotels have resort fees.
• Marriott Bonvoy Brilliant® American Express® Card: Earn 95,000 Marriott Bonvoy bonus points after you use your new card to make $5,000 in eligible purchases within the first three months of card membership.
• Marriott Bonvoy Business® American Express® Card: Earn 75,000 bonus points after you use your new card to make $3,000 in purchases within the first three months of card membership.
• Marriott Bonvoy Bold Credit Card: Earn 30,000 bonus points after spending $1,000 on purchases in your first three months from account opening.

Bottom line

TPG readers Rosalyn and Brian have just enough points to book their post-vaccination Mexican getaway. While they'll be flying there in economy, they'll make up for it with a weeklong award stay at a five-star resort. Plus, you can easily replicate their itinerary if you're looking for a beach vacation of your own.

If you have a destination in mind and need help figuring out your points strategy, send us an email to be featured in the next installment of Cleared for Takeoff.