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By: 10xT Reader Kailash Brodeur

My family took a 10-day trip in sunny Puerto Rico after jumping at the chance to escape the brutal cold in Minnesota and Michigan this past winter.

I’ve been earning points and miles since 2017 and got my parents into the game about a year later. This was our first family trip and we now plan to take one every year together!

We are scattered all over the US, so trying to come up with a place to go visit as a family was difficult since cheap cash/point fares would be different for each of us. Some of us are in the Midwest, some in the South, so where to go and how to get everyone there cheaply was the big question.


Since we wanted to celebrate the end of exams for my brother and sister, as well as my parents’ 30th anniversary, we decided late January was perfect timing, and for those of us in the midwest, we could escape the winter cold  – escaping the Polar Vortex was a definite plus!

Flights to Puerto Rico

We booked tickets back in September 2018 using the Southwest Companion Pass and points to get my parents and sister down to San Juan. My brother used a combination of Southwest Rapid Rewards Points and Delta SkyMiles earned by flying (he’ll join the game one day) while I also used my own SkyMiles.

Editor’s Note: You can read this article to learn How to Earn the Companion Pass.

Southwest Rapid Rewards Performance Business Card

70,000 points after $5000 spend in 3 months, plus earn 30,000 points after $25,000 spend in 6 months of account opening

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My Mom’s Southwest Companion Pass was earned with the Chase Southwest Rapid Rewards Premier Business Credit Card and the Southwest Rapid Rewards® Plus Credit Card back in early 2018 to earn the 110,000 Rapid Rewards points necessary to earn it.

Southwest Rapid Rewards® Priority Credit Card

Earn up to 80,000 bonus points. 50,000 bonus points after $2,000 spend in the first 3 months. Plus 30,000 bonus points after $10,000 spend in the first 9 months

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My brother and Dad flew down from Houston so they had no weather problems getting to San Juan. I, however, was in Minneapolis, dealing with below-freezing temperatures and horrible check-in lines as TSA was stretched thin during the government shutdown.

Thanks to the Chase Sapphire Reserve, I had TSA PreCheck, so I could get through security quickly after checking in so I was able to get to my gate on time. Flying out of Michigan, my Mom and sister were delayed one day because of snowy conditions in Detroit. Thanks to paying for the taxes for their flights using the Chase Sapphire Reserve, their hotel accommodations and food and toiletries were covered by Chase during the delay.

Jobos Beach at sunset
Jobos Beach at sunset

For our flights there and back, we had access to the lounges in San Juan and Baltimore thanks to our Priority Pass Select memberships we have through the Chase Sapphire Reserve.

San Juan Bautista Cathedral
San Juan Bautista Cathedral

Booking Hotels In Puerto Rico

Since my mom, sister and brother all went to Puerto Rico earlier than my Dad and I, they stayed at an Airbnb, which was covered by the $300 Chase Sapphire Reserve travel credit. My Dad and I had each opened a Marriott Card with a 100,000-point sign-up bonus. I earned mine a year before this trip, so I also had a free night certificate in my pocket.

Chase Sapphire Reserve

50,000 Chase Ultimate Rewards Points after you spend $4,000 spend in 3 months

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We used these points to stay at the Marriott Courtyard in Aguadilla on the west side of the Island for the first half of the trip, and then the Marriott Courtyard in San Juan for the remainder. The hotel in San Juan was filling up while we were making the booking because, as we learned later, the orchestra for the Hamilton musical was booked there too! The hallways were filled with music the entire time.

Learning how to Bachata at Aguadilla
Learning how to Bachata at Aguadilla

The Marriott points covered the whole stay including taxes. My Dad and I each redeemed 8 nights — 3 in Aguadilla and 4 nights + a 5th night free in San Juan. We saved well over $2,000 using Marriott points for our hotel stays!

Using the Cash We Saved for Experiences


We were able to use the money that we saved on airfare — $1,000+ for the family — and hotels for adventures into the mountains, a boat trip in a bioluminescent bay, hiking explorations into caves, and visits to coffee plantations! With a nice rental car (thanks to being an Executive Elite member of National, we got a nice upgrade to a Dodge Durango that came with plenty of room for the family, luggage and even a rental surfboard! We drove all over the island!

San Juan at sunset
San Juan at sunset

The Last World

While this wasn’t a luxury first class redemption, we did take an entire family to a wonderful paradise for 10 days for next to nothing. Now, it’s time to plan next year’s family trip!

El Yunque National Forest
El Yunque National Forest

Chase Sapphire Preferred Card

New to the world of points and miles? The Chase Sapphire Preferred is the best card to start with. With a bonus of 60,000 points after $4,000 spend in the first 3 months and 2x points on dining and travel, this card truly cannot be beat! 

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Editors Note: Opinions expressed here are author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

About the Author

Bryce Conway is the Founder of and Author of Takeoff: How to Travel the World for Next to Nothing and How to Fix Your Credit: Do it Once. Do it Right. Get on with Your Life. Bryce’s work has been featured in multiple national media outlets including Good Morning America, Money Magazine, and ABC Nightline News. Bryce created 10xTravel in 2014 and has been hanging out in the points and miles community since 2011....

Learn More About Bryce

3 Responses to “A Family Adventure to Puerto Rico using Points and Miles”

I’d also recommend the Courtyard Isla Verde in Carolina which is a category 4 and close to the airport. Very nice pics! Being from the Midwest I totally understand wanting to escape the cold!

had the points, didn't have the vacation time

What the author downplays here is that while he was in tropical paradise, he left his (definitely not still bitter) girlfriend behind to freeze during the most RECORD-BREAKING part of the Polar Vortex. Minneapolis saw temperatures of -50°F with wind chill, meaning that there was an over 130°F difference in temperature between the author’s lovely home and his vacation.

If anyone would like suggestions of fun activities for their next visit to Hoth, might I suggest:
• Keeping your hands warm with candles
• Not going outside because you could get frostbite in minutes
• Drinking hot toddies

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.

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