Another vacation in the books, and it couldn’t have been better than an (almost) free weekend in the beautiful island of Puerto Rico!

In this post, I’ll share how Josh and I managed to enjoy a 3-night/4-day winter getaway for just $22. Yes, that’s all we paid for flights and hotels!

I’m a huge points and miles enthusiast, and there’s nothing that gives me more satisfaction than using my hobby to score free (well, almost) amazing vacations that make my wanderer’s heart sing with joy. I’ve been using points and miles to travel for free since 2015, but it wasn’t until 2022 that I really took it seriously and became very strategic in my approach. So far, we’ve traveled to Colombia, Costa Rica, Mexico, California, Vegas, Florida, Paris, and Amsterdam for free (again, almost… we always have to pay taxes and surcharges). This year, we’re stepping up our game big time and heading to places as far as Germany, Ireland, and South Africa, all on points. More on that to come.

But let’s get back to the point. Puerto Rico has been on my list for a very long time, and now I wish I had visited sooner. It is absolutely spectacular! The weather, the food, the people, and the beaches are just out of this world!

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Free JetBlue Flights (almost… we paid $22 in taxes)

We used to be devoted fans of JetBlue, relying on the JetBlue card for all our monthly expenses and always paying it off at the end of the month (the golden rule for playing the points and miles game, by the way). However, as we began exploring other points currencies, like Chase and American Express, our loyalty to JetBlue waned, and we stopped using the JetBlue card.

Then, something intriguing occurred. Our oldest credit card is a Sears Citi card (yes, Sears), which we hadn’t used in nearly 10 years but had to keep open since it’s our oldest card. In April 2023, we received a letter stating that we needed to make a purchase or they would close the account, so I made a small purchase to keep it active. About a month later, I received an incredible offer: spend $1,500 each month on groceries, gas, or dining with the card, and get an extra 20,000 Citi points that transfer to JetBlue! This offer repeated for 8 consecutive months, during which we accumulated 160,000 points by making the same purchases we were going to make anyway! It just goes to show how easy it is to accumulate points.

Each round trip from Boston to Puerto Rico was 25,000 points plus $11.20 in taxes. The cash value for the flight was over $400 each. I used the rest of my points to book 5 round trip tickets to Nashville to take my kids in November, with a total cash value of $1,700. I only had to pay $44 in taxes! This means that my regular grocery, gas, and restaurant spend with the Sears card last year earned me almost $3,000 in JetBlue flight value!

The flight was a quick 3-hour direct flight. The airport in San Juan is small and super easy to navigate. Ubers are easily accessible, and our hotel was only 15 minutes away.

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Our Free 3-night Hotel Stay – Hyatt House

We’ve recently become avid fans of Hyatt hotels. Ever since we discovered how to earn and use Chase Ultimate Rewards points (which transfer 1:1 to Hyatt), we’ve been treated to complimentary stays at luxurious and exclusive hotels, like the ones we enjoyed in Paris and Amsterdam, which would have otherwise cost us $500 to $600 per night (you can read more about that adventure here).

Hyatt has numerous properties in the US that are not only centrally located but also quite affordable when using points. For our (almost) free weekend in Puerto Rico, we opted for the Hyatt House in San Juan, which required just 12,000 points per night. The cash value for the same stay was nearly $300 per night, especially since it was during February vacation. It was a standard room with a king size bed, a fridge, microwave, coffee maker, and free hot breakfast. Not the greatest view, but it was free!

We absolutely adored the hotel’s location! It’s just a 5-minute walk to the T-Mobile district, a chic and vibrant area teeming with restaurants, live music, and entertainment. The Sheraton hotel is also a mere 5-minute stroll away, and their restaurant “Metropol” offers amazing and very reasonably priced Cuban-Puerto Rican fusion cuisine (this was the first time we tried the mofongo!) Moreover, it’s within walking distance of Escambron Beach, which boasts several nice ocean-view restaurants. One night, we dined at Havana Grill, and it was a delightful experience. The lagoon nearby is perfect for paddle boarding and kayaking with waters so clear that we saw sting rays from the bridge!

The hotel is about a 10-minute Uber ride to Old San Juan, and there’s also a free shuttle service offered by the hotel. Old San Juan is incredibly lively at night, coming to life after 9 pm. We explored a few bars, and our favorite was La Factoria, owned by the rapper Nicky Jam. It’s said to be among the top 50 bars in the world and features six different “bars” inside, each with its own ambiance, including a speakeasy.

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Ahhhh…. The Beaches!

I’ve visited numerous beaches around the world, and Puerto Rico’s beaches come remarkably close to the top of my list (second only to the Maldives) for several reasons. Just a quick 15-minute Uber ride away, the Isla Verde Beaches are absolutely breathtaking! You can rent an umbrella and two beach loungers for just $25 per day, and there are plenty of food options just a block away. Additionally, there’s a fully stocked CVS pharmacy nearby where you can find ice, liquor, beer, and snacks. The beaches also feature beach bars, long stretches of coast for leisure walks, and the added bonus of no beach vendors and no seaweed! The Uber ride costs only $5 to $7 each way, and if we filled up on the complimentary breakfast at the hotel (complete with made-to-order omelets!), we could easily wait until dinner to eat again. When getting here, use Lifeguards of the Reef as a point of reference for the Uber address.

Another stunning beach that left me awestruck was Luquillo Beach, situated near the El Yunque Rainforest. It was about a 30-min ride from our hotel, and we spent about $100 round trip in Uber. This park/beach is truly a sight to behold, boasting golden and white sands, tranquil turquoise waters, and picturesque mangroves. What’s more, it offers convenient amenities such as clean bathrooms, showers, lockers, and rental services for beach equipment and umbrellas. Adjacent to the beach are the famous “kioskos,” a paradise for food enthusiasts like me. With a plethora of restaurant options available, we ultimately decided on Edelweiss Steak and Bar, and it was a culinary delight beyond words. The stuffed avocados were a revelation—how had I never thought of making them myself before?

So, there you have it—our (almost) free weekend adventure in Puerto Rico, achievable by anyone who learns how to leverage their monthly budget to earn points and miles to redeem for free travel.

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