11 Days Puerto Rico on Points
After a long search for award flights to Egypt this fall came to a futile end, it was decided Puerto Rico was going to be the perfect cold weather escape during November. With a Southwest card full of bonus points, and a companion pass to boot, it was the perfect get away we could plan on a budget. Below I break down how we will be taking a 11-day luxury trip to the Island of Enchantment for less than $800 each.
Flights
Last spring (2023), Southwest ran a special on their credit cards with a 30,000 point bonus including unlimited Companion Pass for a year. As my boyfriend and I often fly together, the companion pass was too good of a deal to pass up. We met the minimum spend within a month and have certainly taken advantage of the great deal (14 “free” flights).
Credit Card Tip: Points are not always the “best” reward when it comes to sign up bonuses. We have booked a total of 14 flights for free this year with the Southwest companion pass. Be sure to always read about the entire sign-up bonus to determine if it’s worth it for you!
After we decided we would pass on Egypt this year, we immediately looked to Southwest’s flight map to see what other destinations could be a perfect vacation. As winter would be starting at home around the time we wanted to travel, a tropical paradise sounded ideal. According to the flight map, there were no flights from Spokane to Puerto Rico, but I wasn’t going to let that stop us.
Booking Tip
Flight maps can be your best friend when searching for flights. Most of the time I will have an idea of what we’re looking for in a vacation (culture, weather, sites), but keep exact locations open. By searching flight maps, it not only gives me ideas on places I may have never thought of, but also shows the best deals from the location you’re looking to fly from. The more flexible you can be with your travel, the better deals you can find!
After a little searching and creative booking, I was able to book round trip flights for both my boyfriend and I for only $45!
Nov 16th Spokane- Orlando 17742
Orlando- San Juan 10126
Nov 24th San Juan- Nashville 12782
Nov 26th Nashville- Spokane 24999
Total Points 65649
My Taxes $22.40
Companion Fare Taxes $22.40
Total Cash $44.80
In order to get to Puerto Rico from Spokane, I had to break the trip into 2 legs. Because we gain 3 hours on our way there, it was an easy trip to make in a day with layovers in Denver and Orlando. The return trip worked out even better because it allowed us to take a long layover in Nashville to visit family for a day. With these 4 flights and the accompanied companion fare, the total was 65,649 points and $44.80 for taxes!
Transportation
Our travel style is adventure, adventure, adventure! Sitting still for too long gives me FOMO, so we are on the go a lot. Puerto Rico is the perfect place for this because it is a small enough island you can drive anywhere and back in a day. In order to enjoy the island to the fullest, I knew we would want a rental car for the entire trip. It is easy to pick up a car from the airport and return it there when you leave.
With my Chase Saffire Reserve card, I am privy to a complimentary Executive status with National Rental Car. This status includes; upgrade from midsize to full-size or larger, priority service, and free second driver. Luckily National had a great rate for our trip, so this was an easy choice. I was able to book directly through the Chase Ultimate Rewards portal allowing me to book with 1.5 cents per point. For the 8 days we were spending in Puerto Rico, I paid a total of 37,634 points ($564 cash value).
Accommodations
In order to keep our driving time to a minimum, we decided to split our nights on the island between the east and west sides. Using Airbnb and hotels will give a great mixture of experiences. Below is a breakdown of where we will be staying each night with how much it cost total in points and cash, including all taxes and fees.
November 16th Hyatt Place San Juan 12,000
17-19th Utuado Airbnb $357
20th Hyatt Regency Grand Reserve Puerto Rico 20,000
21st Hyatt Regency Grand Reserve Puerto Rico $385
22-23rd Hyatt Regency Grand Reserve Puerto Rico*** $1463
24-25th Hyatt House Nashville Airport 16,000
Total: $2,205 and 48,000 points
As you can see, all of our hotel stays are at Hyatt Hotels. The Hyatt’s in Puerto Rico are resorts with ocean view rooms, restaurants, and private beach access. Although luxury, these are NOT all inclusive. The nights notated with *** include a “Stay and Play” package with breakfast for two and two rounds of golf per day at the Grand Reserve Golf Club (home to the Puerto Rico Open). Rounds at the Grand Reserve normal are $195 per person.
Booking Tip: The nights of the 20th and 21st had to be booked separately due to holiday award night black outs. When I originally searched for all the nights together, it did not look like I would be able to book any nights with points, but after I took the time to search each night separately, I was able to save well over $300. Sometimes the trick to finding the best award deals, whether it be hotel nights or flights, is to be creative with your searching, and again, be flexible!
Summary
For an 11 day luxury trip for two, including airfare, transportation, and accommodation, we have spent $2,250. That’s less than $1,200 each! If you discount the “Stay and Play” nights to the normal nightly rate (for those not into world class golf), the total is less than $800 each! If this is all foreign to you and you are interested in learning more, be sure to follow along as I dive into even more tips and tricks on travel hacking! Also don’t hesitate to reach out if you have questions or want some help planning a trip. I truly get a kick of this and would love to lend a helping hand.
