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Maximizing Rapid Rewards and Companion Pass for an Anniversary Trip to the DR

Aviator A

I started almost exclusively flying Southwest in 2013 after moving to Nashville, where the airline has a large presence. Having held status with another major carrier, I was not sure what to expect, and I knew I would miss the occasional first class upgrade and the ability to always pick my favorite seat on other airlines. That said, I was pretty intrigued by the way my coworkers raved about the experience of flying Southwest.


Soon enough, I was completely in LUV with that experience, and it is crazy how quickly Southwest and its Rapid Rewards points and loyalty program became a part of my story. The flexibility of Southwest’s policies was a key part in Making Long Distance A Little More Bearable when my wife and I were dating. Today, the points I accumulate and Companion Pass allow us to travel in ways we couldn’t otherwise. Now that we have our own Little Southwest LUVer (two actually), we have mastered traveling with children as well!


Recently, we had been trying to decide what to do for our fifth wedding anniversary.  After lots of discussion, we landed on returning to the Dominican Republic where we honeymooned. If you have been, you know it is a beautiful place!

Photo: Majestic ColonialPhoto: Majestic Colonial

Since then, our family has grown a bit.

Photo: Brigette Billups PhotographyPhoto: Brigette Billups PhotographyAs much as we love traveling with our kids, we have earned some alone time back in the Dominican Republic!  Last time, we stayed in Punta Cana, but this time, we decided to explore a different part of the island, La Romana.


After doing some research, I found a magic combination of hotel and flight reservations, and, as any good Community Champion would, I want wanted to share some tips on how to I get the best possible value out of the Southwest Rapid Rewards program!


First off (and unrelated to Southwest) was the incredible hotel points redemption I found at an all-inclusive in the DR! I have lots of hotel points from my business travels, but I still like to use them conservatively. We got lucky booking a newly-renovated all-inclusive for five nights for both of us for fewer points than I could have booked two nights at many domestic hotels. Jackpot!  If you don't have hotel points available, you can book hotels directly through Southwest!


We had to wait a while to book our flights because Southwest had not released the schedule for our travel timeframe. (By the way, you can always see the upcoming release date on the Low Fare Calendar on Southwest’s website.) Once the schedule was released, I quickly booked our tickets, and I was in awe of how much value Southwest once again offered!


Here’s the plan: all four of us fly from Nashville to Houston to drop our daughters off with their grandparents (thanks, grandparents). Then, my wife and I fly the next day from Houston to Punta Cana for our trip. We’ll fly back to Houston in time for Thanksgiving with the wife's family and then head home to Nashville after the holiday.


All this translates to a few different bookings with a combined cash value of around $3,000: $760.00 x2 for the round trip from HOU to PUJ, $381.00 x4 for the round trip from Nashville to Houston. That’s not what we paid; however, not even close! In fact, our total out of pocket cost was about $650.


So, how did we do it? I’m glad you asked!


It all came down to a magic combination of points, Southwest’s Companion Pass, and the ability of our youngest to travel as a lap child. Here‘s how I booked it all:


  • First, I booked my ticket to Punta Cana from Houston on points. Retail value was around $760.00, but it only cost me some 38,000 Rapid Rewards points plus $120 in taxes. Then, I booked my wife using her Companion Pass – she travels for free, excluding taxes. Domestically, that would only cost around $11 round trip, but because Punta Cana is an international destination, taxes were actually $120.00, bringing our total cost to roughly 38,000 points plus $240. Approximate savings: $1,280.00! Even better, Southwest launched a sale a few days after I booked, and the cost of the flight went down; I was able to rebook and save around 1,500 points!  And then it happened again...another sale, another rebooking to save more points.
  • Next, I booked the trip to Houston for the whole family. This one is a little more complex. Although I had the points to cover tickets for all of us, I decided to pay cash for my flight so it would count toward my A List status (points bookings do not count). The cost was about $381.00 for me. Once again, I was able to add my Companion/wife for about $11 in taxes. Our youngest is a few months old and flies free as a lap child, and I booked our older daughter’s ticket using points. Total cost for this portion: about 25,700 points plus $405.00. Approximate savings: $1,120.00!


My wife stays at home to raise our family, so value like this is how we can afford to travel! And had I used even more points, I could have done this whole plan with only about $270.00 out of pocket — less than a tenth of the cash value of the flights.


So how does one do all this? First, you have to fly a fair amount. I do indeed have a ton of points from my business travels, and while my being away is not always ideal, the opportunities those accumulated points offer our family are a good trade-off. Second, make the most of Companion Pass. There are a few different methods to securing one, and it is without a doubt the best loyalty perk in the business. Third, do your research and learn all about Southwest’s flexibility; the Community here is a great place to learn, and the growing Knowledge Base is a good reference point along with Southwest’s website.


Now, a couple nuances came into play here, especially with the BNA to HOU and HOU to BNA flights. The way I booked the reservations required each traveler to be on his or her own reservation (since I was using a combination of cash, points, Companion Pass). After booking my ticket, I found the reservation in my Rapid Rewards account and selected “Add Companion” to add my wife. Next, I booked my daughter’s ticket on points by selecting the right flights while logged into my Rapid Rewards account. When using your points to book for others, after you select the flights, you will remove your own pre-populated info from the traveler details fields and then add the info of the person actually traveling. As a final step, since my daughter is a minor, the system automatically prompted me to enter my own reservation information to show she would not be traveling alone and to link the reservations. Finally, I booked the BNA to HOU leg and the HOU to BNA leg separately. While it wasn’t absolutely necessary to book them that way, this is a common best practice mentioned on the Community because it makes changing the flight easier or rebooking easier if prices go down.  Also, I will add our youngest as a lap child at the airport the day of travel, and I will have to show a copy of her birth certificate to prove her age (under two).


Beyond the booking process, we will have no additional costs related to this trip except for airport parking. Unlike other airlines that charge for checked bags, Bags Fly Free on Southwest!


Boarding with the whole family does get interesting due to how these tickets are booked; since we are not all on the same reservation, we will all have to check in separately meaning we will all have boarding positions that will not be together. This could be a whole other post in itself, but the best option we have here is to board during family boarding after the A group. You can learn more about boarding Southwest flights here.


At the end of the day, every traveler is different. We all fly at differing frequencies; we all have varying degrees of loyalty to one or more airlines. Value like this, along with the incredible experience Southwest employees provide for their customers (just ask J.D. Power) is why I choose to fly Southwest. No other airline would offer me this much value for this particular situation or for our overall travel needs as a family.


I encourage you to join Rapid Rewards if you have not done so already!  If you want to learn more about how to create magic like this, the Southwest Community can be your best friend.  Before you know it, you might just have some travel inspiration of your own to share!


Peace, LUV, and happy flying!