An (Almost) Free Week in Cabo San Lucas — Reader Success Story

Jul 18, 2017

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One of the things I love most about being The Points Guy is getting to hear stories from readers about how award travel has affected their lives — the exotic vacations they’ve planned, the trips they’ve made to be with family and friends, the premium seats and suites they’ve experienced and so much more, all made possible by points and miles. I love to travel and explore, and it’s an honor to be able to help so many of you get where you want to go.

I like to share these success stories to help inspire you the way you inspire me! From time to time I pick one that catches my eye and post it for everybody to enjoy. If you’re interested in sharing your own story, email it to; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. If we publish it, I’ll send you a gift to jump-start your next adventure!

Today I want to share a story from TPG reader Dennis, who used one of the most valuable travel perks out there to help book a vacation in Mexico. Here’s what he had to say:

Southwest Rapid Rewards points can be very useful, especially if you earn the companion pass.
Dennis used the Southwest Companion Pass to book two award flights for the price of one.

My wife and I recently took a week-long trip to Cabo San Lucas, Mexico over the long Fourth of July weekend. Thanks to two major travel perks I earned by following your advice — the Southwest Companion Pass and the sign-up bonus from the Chase Sapphire Reserve card — we were able to cover nearly all of our expenses with points and other rewards!

In late 2015, I decided I would embark on the challenge of earning the Southwest Companion Pass. After earning sign-up bonuses from both the Southwest Rapid Rewards Premier Credit Card and the business version, I achieved that feat in January of 2016, giving me almost two full years of Companion Pass status! We have since used it to travel to Boston, New York, Austin, LA, Chicago, Houston, Mazatlan, San Francisco — and most recently, Cabo!

For my portion of the flight, I wanted to book a Southwest award from Seattle to San José del Cabo for 23,000 points round-trip, but I didn’t have any Rapid Rewards points left from my credit card bonuses. This is when my 100,000-point bonus from the Sapphire Reserve card came in handy. Since you can transfer Ultimate Rewards to Southwest, all it took was a couple clicks and I had the points I needed to book my flight on Southwest. I then added my wife as my companion, and we were set to go!

I knew I wanted to stay at the Hilton Los Cabos, but I didn’t have enough Hilton Honors points since I don’t usually stay with Hilton (I’m a loyal Starwood guy). Instead, I decided to book directly through the Ultimate Rewards portal to get 1.5 cents per point on redemption, and I was able to find a room for just $180 per night (normally $350-400). That meant I paid just 12,000 points per night, or 72,000 points total for six nights at a beautiful four-star property right on the beach in Los Cabos!

We utilized our $300 annual travel credit from the Sapphire Reserve card to cover the cost of our rental car for the week. On top of that, we got lounge access in SEA and SJD thanks to my Priority Pass membership, and we used Mobile Passport to zip through a line of about 120 people when arriving at customs back in the States.

Thanks for all the value you provide to those of us traveling on a budget!

Ultimate Rewards has a solid roster of transfer partners, but they may not always suit your needs. One major benefit of the Sapphire Reserve card is that you can book a wide range of flights and hotels at a decent rate by redeeming directly through the Ultimate Rewards travel portal. Dennis couldn’t easily transfer points from Chase to Hilton, but the portal enabled him to use his rewards while taking advantage of a great price at his hotel of choice. When transfers and direct redemptions are both available, do the math to see which option is better.

The Southwest Companion Pass remains one of the most valuable travel rewards out there. Transfers from hotel programs no longer count toward Companion Pass status, so if you can’t earn the requisite 110,000 points by flying, the co-branded Southwest cards are a good bet to help you qualify. The airline continues to expand its route network (including new international destinations), and CEO Gary Kelly recently reaffirmed that adding service to Hawaii remains a priority. If you live in a city where Southwest service is reasonably convenient, the Companion Pass is hard to beat, and that doesn’t appear to be changing anytime soon.

By redeeming directly through Ultimate Rewards, Dennis was able to take advantage of a low rate at the Hilton Los Cabos.

I love this story and I want to hear more like it! To thank Dennis for sharing his experience (and for allowing me to post it online), I’m sending him a $200 Visa gift card to enjoy on future travels, and I’d like to do the same for you.

Again, if the strategies you’ve learned here have helped you fly in first class, score an amazing suite, reach a far-flung destination or even just save a few dollars, please indulge me and the whole TPG team by emailing us with your own success stories (see instructions above). Feel free to also submit stories of your most egregious travel mistakes. In either case, you’ll have our utmost appreciation, along with some extra spending money for your next trip.

Safe and happy travels to all, and I look forward to hearing from you!

Featured image courtesy of Gfed via Getty Images.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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