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

Jun 1, 2021

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Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic 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.


Puerto Rico is a beautiful destination full of history, rich culture and year-round beach weather. Being a U.S. territory, you can fly there without a passport and won’t need to worry about money conversions, international data plans or major language barriers. It’s even more attractive now in the age of coronavirus because vaccinated travelers aren’t required to provide a negative COVID-19 test for entry and U.S. citizens don’t need to get tested before returning to the mainland.

TPG reader Alyssa Haring reached out to us for advice on booking a trip to Puerto for her family of four. They’ll be departing from the Northeast and want to spend at least five nights there. More specifically, they’re willing to fly from Philadelphia International Airport (PHL) or Newark Liberty International Airport (EWR) and hope to visit in December.

Alyssa has a mix of Chase Ultimate Rewards points, Hilton Honors points, Marriott Bonvoy points, JetBlue TrueBlue points and American Airlines AAdvantage miles.

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In This Post

Current points stash

Although Alyssa is off to a good start, her points might not be enough to cover the entire family’s vacation. Ideally, she could get the rest of her family to start earning their own points to reach their goal faster. We’d also like to see her diversify the types of points she earns a bit more going forward. For instance, in addition to Chase Ultimate Rewards, she should try to earn other transferrable rewards, such as American Express Membership Rewards points and Capital One miles.

Here are all of the points she currently has:

  • 90,000 Chase Ultimate Rewards points.
  • 20,000 Hilton Honors points.
  • 9,000 Marriott Bonvoy points.
  • 900 JetBlue TrueBlue points.
  • 13,000 American Airlines AAdvantage miles.

Related: How to refer friends and earn points, miles or cash credits

Airfare to Puerto Rico

Route: PHL-SJU

Miles needed: 10,000 American miles + $5.60 per person

There are nonstop flights to San Juan Luis Muñoz Marin International Airport (SJU) from several U.S. gateways, including Philadelphia and Newark. Given her existing stash of AAdvantage miles and its frequency of direct flights from Philly, I’m going to recommend she fly American Airlines.

American usually charges 15,000 miles for a one-way saver award in economy, or 12,500 miles on off-peak dates. However, you might be able to find cheaper awards through American’s Web Specials. While these awards are priced dynamically, it’s not uncommon to find Web Specials to Puerto Rico for as low as 10,000 miles each way. As with any other domestic flight, the taxes and fees on these awards are just $5.60.

Related: How to fly to the Caribbean, Mexico or Central America for the price of a domestic award

AA Web Special
(Photo courtesy of American Airlines)

How to book this award with points

Booking this award is no different than any other American Airlines flight. Simply head to aa.com, enter your route (PHL-SJU), select your dates and check off the “Redeem miles” box.

AA PHL SJU Award
(Photo courtesy of American Airlines)

To find the cheapest dates, try using the calendar search tool available on the search results page.

AA PHL SJU Award
(Photo courtesy of American Airlines)

After you’ve selected a flight, you’ll need to log in to your AAdvantage account to complete the booking. The taxes and fees on this ticket should come out to $5.60 per person. Although Web Specials are not changeable, you can cancel them and redeposit miles for free.

Related: Maximizing redemptions with American Airlines AAdvantage

AA PHL SJU Award
(Photo courtesy of American Airlines)

How to earn enough miles for this award

Alyssa currently only has enough miles to book about one of these flights. She’ll need to earn some more miles to book the rest of her family’s flights. One way to quickly earn AAdvantage miles is by signing up for a cobranded American Airlines credit card:

The information for the Citi AAdvantage Platinum Select, Citi AAdvantage Business Platinum Select, AAdvantage Aviator Red and the AAdvantage Aviator Business cards has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Airfare from Puerto Rico

Route: SJU-PHL

Miles needed: 11,000 British Airways Avios + $5.60 per person

I recommend Alyssa and her family also fly American for their return. However, this time they book their flights through British Airways Executive Club. Although she technically doesn’t currently have any British Airways Avios, she can get them easily by transferring points from her Ultimate Rewards balance.

Related: 11 times it’s better to book American award flights through British Airways

How to book this award with points

British Airways lets you book partner awards directly on its site. There just needs to be saver award space available — a.k.a. the awards American usually charges 12,500-15,000 miles for.

Sign in to your British Airways account, go to the “book flights with Avios” page and put in your search details.

British Airways award search
(Photo courtesy of British Airways)

If you’ve already confirmed availability on another site, the same award availability should appear for the date you search. If not, you can easily search plus or minus three days at the top of the results page. If you still can’t find any award availability, you can subscribe to ExpertFlyer (owned by TPG’s parent company, Red Ventures) and set alerts to be notified when award space opens up.

British Airways award search results
(Photo courtesy of British Airways)

British Airways uses a distance-based award chart. Since the flight between San Juan and Philadelphia is between 1,152 and 2,000 miles long, the one-way economy award should come out to 11,000 miles.

BA AA award price
(Photo courtesy of British Airways)

How to earn enough miles for this award

As mentioned above, Alyssa can get all of the points she needs to book these flights by transferring her existing Chase Ultimate Rewards points to British Airways Executive Club. Chase points transfer to British Airways at a 1:1 ratio and typically post instantly. If you’re looking to replicate this itinerary and are starting with a zero balance, you can also transfer points from Amex Membership Rewards and Capital One. Here are some of the highest welcome bonuses available right now:

Related: A 5-star trip from Phoenix to Dubai for two

Puerto Rico hotels you can book with points

There are plenty of points hotels on the island, including Hyatt, Hilton, Marriott, IHG and even Choice Hotels. It’s also great that Alyssa wants to spend five nights there because several programs — specifically, Marriott, Hilton and IHG — provide opportunities to pick up the fourth or fifth night free on award stays.

Since Alyssa already has a stash of Hilton Honors points, that’s the program I’d recommend she focus on. Hilton offers seven hotels to choose from in Puerto Rico.

Related: 8 things that make Puerto Rico the place to visit right now

The Hiltons are all located in the San Juan area except for the Hilton Ponce Golf & Casino Resort. On-site amenities include a 27-hole golf course, beautiful pool, tennis courts and one of the largest casinos on the island. It isn’t the fanciest Hilton property in Puerto Rico, but with an oceanfront patio room typically costing 50,000 Hilton Honors points a night, it’s a pretty good deal. And although the hotel usually charges a resort fee, it’s waived on award stays.

Hilton Ponce Puerto Rico Pool
Hilton Ponce Golf & Casino Resort (Photo courtesy of Hilton)

Looking at the San Juan area, your options range from the Caribe Hilton to the Condado Plaza Hilton, DoubleTree by Hilton Hotel San Juan, two Embassy Suites properties and the Hampton Inn & Suites San Juan.

Fun fact: The Caribe Hilton was the first international Hilton hotel when it opened in 1949. But don’t worry, it’s been gut-renovated since then and has a nice, modern look now. They’re currently all pricing out at 50,000-60,000 points per night, though we’ve seen some of these properties available for around 40,000 points per night during less-busy periods.

Hilton Puerto Rico map
(Photo courtesy of Hilton)

To get her fifth night free, Alyssa needs to have Hilton Honors elite status. Luckily, she can get automatic status by having any of the cobranded Hilton cards in her wallet. Plus, she may get extra perks like daily food and beverage credits and upgrades if she gets Gold or Diamond status, offered by Hilton’s mid-tier and premium credit cards.

Since Alyssa currently only has 20,000 Hilton points, the cobranded cards will also help her earn the remaining points she needs to book her stay.

Related: How to maximize longer hotel stays by using a free night benefit

How to earn hotel points

You can currently get an elevated welcome bonus on several of Amex’s Hilton credit cards. Again, they all come with varying levels of automatic elite status.

The information for the Hilton Aspire Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Bottom line

No matter where you’re traveling too or how big your group is, there’s likely a way to get there on points. Aside from the balmy weather and beautiful sights, Puerto Rico is a particularly enticing destination given the array of direct flights from the U.S., points hotels and lack of passport requirements. 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.

Featured photo by Maremagnum/Getty Images.

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