I’m going to flash back to 2017. I had run into an old classmate in the grocery store and we chatted briefly about a trip she had posted pictures of on her social media. She told me all about how she was able to fly her family of 4 to Disney on points she earned by using a Southwest credit card. She said they basically put all of their expenses on the card and easily racked up enough points to cover their flights each year. Well this was something new to me so I went home and starting reading up on the Southwest cards! At this time, I also had a side hustle which I used a Citi Diamond card to pay for all expenses over the last year. I had a thought, if Southwest offered traveled points, maybe Citi did as well! Low and behold, I had over 100k points on my card! My husband and I had already booked a rather expensive 10 year anniversary bucket list trip to Hawaii and we had also always wanted to go to Napa Valley since we love ourselves some wine tasting (Ok I love myself some wine tasting and my husband indulges me). At this point, I still had no idea really how this point thing works so I just followed a link on Citi’s site to their travel portal. I realized I could book a stay at a Hampton Inn just outside downtown Napa and a car rental for 2 days completely on points! Since we had spent a mint on our Hawaii trip, I knew this was the only way I was going to be able to convince my husband to make a 2 day pitstop in wine country. I remember that first booking was such a rush! I just kept thinking, did I really just get 2 nights in Napa for free?!?! There had to be a catch! Spoiler alert, there was not a catch! About this time, I also decided to apply for the Southwest personal card to take a long with us to Hawaii and pay for our expenses during out trip. At that point in time, I didn’t realize i could have got more bang for my buck out of bank credit card opposed to a co-branded card but more to come on that later.
We took off to the Napa Valley and the Hawaiian islands in August of 2017! Flying United direct to SFO we spent the first day exploring San Francisco including Fisherman’s Wharf, the Painted Ladies, Golden Gate Bridge, and Muir Woods. We then drove up to Napa in our Cadillac rental paid for completely on points to stay in our Hampton Inn room a few blocks outside of downtown Napa paid again with points! The second day, we bounced around wineries started in Calistoga at a real castle built from material brought in from Italy, Castello di Amorosa! We took the tour through out the impressive grounds, tasted wine straight from the barrels in the wine cellar, and then had an official 10 sip tasting in their tasting room. From there, we went off to see the grounds of Berringer, walked around Frances Ford Coppola’s winery Inglenook, sipping wines at Robert Mondovi that were only available to those that visited the winery, and ended the day at Domaine Carneros sipping Pinot Noir on a beautiful balcony overlooking the vineyards. Did we have to pay for the tastings and wine we drank and purchased, yes, but not having to pay the almost $1000 it would have cost us for boarding and transportation, was HUGE! Points made this bucket list stop a reality for us!
The next day we were back at SFO and ready to jet off to Hawaii! It was our goal to go there for our honeymoon, but unfortunately just was not financially possible at that point in our lives so getting there to celebrate 10 years of marriage was a huge goal of ours. We spent 8 days first exploring Oahu. We stayed right on Waikiki Beach at the Outrigger Resort. Again, we had splurged on ocean front rooms and our view also included Diamondhead, so we were living the dream! Instead of renting a car for the whole trip (price of parking is INSANE in Oahu) we just did a one-day rental and drove the island up to the north shore. We saw turtles, swam in a waterfall, ate at the food trucks, and topped it off with shaved ice! We also rode an Outrigger canoe which was by far the coolest thing I’ve done! We then went off to Maui staying in the Wailea area at the Marriott. The resort had been recently renovated, sat on a cliff overlooking the Pacific and was walking distance to 2 beaches. There was an adult only infinity pool and we decided to rent a pool cabana for the day. HIGHLY recommend this! We had pool service all day, no worries about trying to claim chairs, and the cabana was sat in the middle of the pool area looking out on the ocean. We spent some time at Wailea Beach which also chair and umbrella rentals available, and took a full day guided trip to Hana. Our local guide was amazing, and we saw everything from waterfalls to bamboo forests, ate lunch on a horse ranch, swam in a black sand beach, and the guide took us along the back part of the island to see the differences in topography. It was an amazing, all be it long, day of adventure! (Travel tip: if you are planning on swimming in waterfalls, bring water shoes!). Before we knew it, it was time to make the long trip back to the east coast. We vowed we would get back to islands again for more adventures! Little did I know, I was going to be able to make that a reality, but this time rooms and flights would be paid with points!
On our adventure through the Napa Valley and Hawaii, we took along our brand-new Southwest card and paid for expenses using that card. Due to some things in our personal life, we didn’t travel much between 2018 and 2020 so during that time we were able to rack up over 100k Southwest points just paying for daily expenses. When it came time to book a flight in 2020 to Florida, I was able to do so round trip using only 30k Southwest points and I was officially hooked! Over the past 3+ years, we have been able to fly domestically without paying anything except for taxes and fees on flights. This has saved us at least $5000 or more! In my next post, I’ll talk about my first FULLY paid for travel hacking trip that we just took in September 2023 to Sedona, Grand Canyon and Las Vegas!