2016 was a hell of a year. I went from traveling full-time, to falling in love, to settling down in Phoenix, Arizona. Now, I’m working the most kickass job I’ve ever had, which is GREAT for my career. However, those mere 16 days of PTO every year are not so great for my travel habit.

Having only 16 PTO days meant that a larger international trip was slightly harder to plan this year. JT and I were left scratching our heads to determine exactly where our 2017 travel destination(s) would be.

Then, the heavens opened up and handed us a low-key miracle — the Southwest Companion Pass.

Back in November 2016, I entered a contest to win a Southwest Companion Pass from The Points Guy. I didn’t expect much to come from it, especially when I learned that nearly 20,000 people had entered to win only 20 passes. A week later I learned that I was one of 20 winners who would have a Companion Pass added to their Rapid Rewards account the following week.

If you’re unfamiliar with the Southwest Companion pass, it’s the most ridiculously awesome airline perk ever created. It’s difficult to earn (you need to take 100 one-way Southwest flights in a calendar year to qualify), but that’s why it’s so incredible. Once you have earned the Companion Pass, ANY Southwest flight you take through December 31st of the following year, you get to take one “Companion” with you for FREE. Well, actually you do still have to pay tax on the Companion’s ticket, which is $5.60 each way for domestic flights.

So what does that mean?

That means if I booked a trip ANYWHERE Southwest flies, JT could go with me for TAX ONLY, throughout all of 2017.

Naturally, we were absolutely ecstatic to win this elusive perk. We were even MORE excited when we saw that Southwest dropped 110,000 points into my Rapid Rewards account to be used with the Companion Pass! We were looking ahead to a 2017 of nearly free travel anywhere Southwest flies.

Some of you might be scoffing at this… “Anywhere Southwest flies? Big deal. They only do domestic flights, right?”

Wrong, Miss Debbie Downer! In the past few years, Southwest has expanded its flight routes to include international routes to Mexico, Costa Rica and the Caribbean.Southwest Companion Pass_Southwest Route MapWith so many possibilities and the opportunity to fly two-for-the-price-of-one, we started planning early. Our first step in planning 2017 travel with the Companion Pass was to select our destinations. We booked the “BIG” trips we want to take first, planning for five days off work in between weekends to maximize my PTO in both cases. We booked smaller “weekend” and “long weekend” trips as the year went on.Southwest Companion Pass_Sailing with San Diego Sailing ToursJanuary

I used to live in San Diego, and it still has my heart. We received an offer from San Diego Sailing Tours to join them on a sail, so we were BOTH off to San Diego (roundtrip and last minute) for only $200 total (taxes incl.) using the Companion Pass. Southwest Companion Pass_Beach on Klein CuracaoSouthwest Companion Pass_Lighthouse on Klein CuracaoSouthwest Companion Pass_Shipwreck on Klein CuracaoApril

“Aruba, Jamaica, ooh I want to take you to Bermuda, Bahama, come on pretty mama…”

I’ve been dying to visit Aruba for a long time, and in April, it finally happened! We spent four days in Curaçao and five days in Aruba, snorkeling, sunbathing and eating/drinking the days away.

We used my Rapid Rewards points gifted from Southwest to book these flights, meaning we only had to pay the taxes which came out to $75.16 per person. $75.16 PER PERSON TO GO TO ARUBA…ROUNDTRIP. Plus, we used our $300 2017 travel credits from the Chase Sapphire Reserve card (I’ll be writing about this credit card soon in exhaustive detail, because I’m pretty obsessed with it). In total, we paid exactly $0.00 for the airfare for this trip. Winning!Southwest Companion Pass_Royal Caribbean Harmony of the Seas_A Kiss on DeckSouthwest Companion Pass_Fort in St. KittsSouthwest Companion Pass_Blue Water of St. JohnJune

We threw around a bunch of different destinations for this trip, and decided that we simply couldn’t resist another cruise. If you know us, you know we LOVE cruising. We were thrilled to hit the high seas once again on the world’s largest cruise ship: Royal Caribbean’s Harmony of the Seas. The itinerary included four different islands: Nassau, St. Thomas, St. John and St. Kitts. Rapid Rewards points gifted from Southwest paid for my flight, and JT’s was free with the Companion Pass…meaning we only had to pay the taxes. Taxes came out to $11.20 per person roundtrip, which we also paid with our Chase Sapphire Reserve $300 credit. That’s a damn good deal, considering a standard roundtrip fare from Phoenix to Fort Lauderdale currently runs around $600 per person!Southwest Companion Pass_Silver Dollar Lake TrailSeptember

We were itching to go again, so we took off to Denver. It was a close flight for us, and we were able to take in the sights in Golden, Boulder and downtown Denver in 48 hours. We also went on a hike with friends on Silver Dollar Lake Trail, near Georgetown. It was the perfect quick getaway, and with the Companion Pass, it cost us only 16,600 Rapid Rewards Points and $22.40 for taxes total. You can’t beat that!Southwest Companion Pass_Golden Gate BridgeOctober

In October, my Aunt’s 90th birthday party had us looking at flights from Phoenix > my hometown of San Jose, California. Because we never do ANYTHING small, we tried to see how much we could pack into that weekend away, and ended up going a little nuts. We flew up to San Jose on Saturday, visited family and went to the Winchester Mystery House (one of my favorite haunts…pun intended).

After celebrating my Aunt’s birthday with her Saturday night, we drove to San Francisco on Sunday morning and spent the day playing tourist in the city that is my second home. Monday morning, we got up at 3:45 a.m. to catch the 4:10 a.m. BART train from SF to Oakland, where we hopped a flight to Anaheim. Then, we spent two days at the Happiest Place on Earth before heading home. It was a whirlwind few days, but worth every second! The best part is that it cost us barely anything once again, with the help of the Companion Pass.


As you can see, it was an action-packed year…even though I was only working with 16 days of PTO. We visited THREE new countries and some of our favorite cities in the US.

We’re so grateful for the gift of the Southwest Companion Pass. It was an incredible year of new adventures and we can’t wait to see what 2018 brings!

What is your favorite destination that Southwest flies to? Tell me in the comments below!