After a lengthy planning process and multiple revisions to our itinerary, we were finally ready to explore the beautiful island state of Hawaii. With our negative COVID test results uploaded to our State of Hawaii travel profiles and having expertly skirted the upcoming changes in testing procedures required upon arrival, we set out at long last. Tropical paradise, here we come! Would we experience any other hiccups along the way? How much would it cost? Check out my Travel Hack Recap of Hawaii – West Maui below!
To read Hawaii, Part 1 – The Backstory, click here.
Where We Went
You get it by now. We went to Hawaii. But after multiple flight changes, our first night would actually be spent in San Jose, California before setting out the next day for 9 nights spanning several different regions of Maui.
I usually arrange these travel hack recaps by category (flights, transportation, accommodations, etc.), but I think it’s easier to follow along if I just go chronologically for this trip.
Day 1 – Minnesota to California
I’ll try not to belabor the point anymore, but the hardest part of planning this trip was just getting there. Since a negative COVID test was required within 72 hours of our flight leaving the mainland, we did a day of repositioning to end up in California so that we could leave for Hawaii early the next morning.
Sunday, May 2 saw us take an evening Southwest flight from Minneapolis to Denver. We were supposed to have less than an hour layover in Denver, but in what would become a recurring theme, we were delayed. Southwest still seemed to be really struggling with their logistics, since my flight home from Charlotte was also delayed nearly 2 months before. We ended up arriving in San Jose just before midnight.
Once we finally arrived in San Jose, the real saga began. We chose to stay at a hotel in close proximity to the airport (Hyatt House San Jose Airport) specifically to make use of the complimentary shuttle. But after arriving just before midnight, waiting on our luggage to arrive (we checked one suitcase due to large bottles of sunscreen), the shuttle was no longer running.
No big deal, we’ll just take an Uber or Lyft, right? Wrong. Not a single one to be found. I hope this has improved as more cities have relaxed their COVID restrictions, but at the time, we had at least one plane full of people competing for extremely few drivers all at once. After about a 45 minute wait, we finally found a ride, arriving at our hotel around 1:30am. Not ideal with a 6:50am flight looming, but we made it.
Day 2 – California to Maui
With just a couple short hours of sleep, we loaded up on coffee and headed to San Jose airport (SJC) early Monday morning for our 6:50am Southwest flight to Maui Kahului (OGG). Luckily we caught the hotel shuttle.
Thanks to the research Mrs. FIby35 had done ahead of time, we had all of our travel documents in order. We walked up to our gate, presented some paperwork, and were promptly provided with wristbands from the gate agent. These wristbands would be key to avoiding unnecessary delays upon arrival in Hawaii.
Speaking of unnecessary delays, our flight out of SJC was delayed…not significantly, but just long enough to piss us off in our sleep-deprived state. Seriously, you couldn’t check the plane out ahead of time? But about 5 hours later, we were soaring over the vast volcanic landscape of Maui and all the stress and sleep-deprivation melted away.
Kahului to West Maui
Emboldened by my public transportation win in Charlotte, I did a fair amount of research on the public transit options on Maui. Turns out, they have a pretty extensive city bus service, aptly named “The Bus.”
I had meticulously planned a route from Kahului airport to the Queen Ka’ahumanu Center (a local mall and transit hub in Kahului), continuing on to the Wharf Cinema Center in downtown Lahaina on the west side of Maui, before finally reaching our closest bus stop in Whalers Village on Ka’anapali Beach, just a few minutes walk north of our hotel. All for just a $4 day pass each!
Given our frustrations with delays thus far, we scrapped that plan and took a Lyft straight to our hotel. For a budget enthusiast like myself, we were not off to a good start in the Spreadsheet category. But we made it!
Ka’anapali
We spent 3 nights in West Maui at the Hyatt Regency Maui on Ka’anapali Beach, booked just a week or so in advance by transferring some Chase Ultimate Rewards points to our Hyatt accounts. This was by far the nicest property we stayed at in Hawaii, and it was all for free (plus 75,000 Hyatt points). Our Hyatt status resulted in a free room upgrade, ending up with a phenomenal view just feet from the beach – we could see sea turtles floating in the waves below.
After lunch at the on-site beachside restaurant, we soaked in the views and sun for the rest of the day. Exhausted from a full 24 hours of travel and thrown by the time zone difference (5 hours behind CST), we headed to bed shortly after sunset, which would be common over the next few nights.
Day 3 – Napili Bay & Whalers Village
Our first full day in Hawaii began by testing my public transit skills – we walked from our hotel to Whalers Village and caught The Bus up the coast to have breakfast at an awesome spot called Gazebo. The view over Napili Bay was breathtaking and the macadamia nut pancakes were phenomenal. Back in Whalers Village ($4 bus day pass FTW), we picked up some groceries at the ABC Store – that’s where I experienced my first bout of sticker shock.
I had heard all the stories of how expensive Hawaii is, so I wasn’t totally unprepared. But I was not about to pay $22 for a 12 pack of Kona Big Wave that costs about $14 back home. I resolved to stay sober rather than spend that outrageous sum on beer (spoiler alert: I didn’t last long). So we got some fresh fruit and were on our way. We had scoped out happy hour at Monkeypod Kitchen, a popular Hawaiian restaurant chain, for dinner and it did not disappoint. Highly recommend the place, as the happy hour deals make it much more affordable – just don’t end up like Miles Teller.
Day 4 – Lahaina
The following day was spent testing more skills, as I attempted snorkeling for the first time at Black Rock Beach. I’m not a strong swimmer, but I actually enjoyed it. We even saw Hawaii’s state fish, the Humahumanukunukuapua’a.
Later that day, we hit The Bus again to downtown Lahaina, an old fishing village just south of Ka’anapali Beach. It’s a bit touristy, but there are some cool historical landmarks and one of the largest banyan trees in the US. We had happy hour lunch/dinner at Down the Hatch before continuing on to Kohola Brewery a short walk away from the busy downtown area. Kohola has won several awards, including Thrillist’s list of Most Underrated Brewery in Every State in 2019. Throw in some happy hour pricing and I’m one happy tourist.
Day 5 – Ka’anapali & Kahului
On our last day in West Maui, we spent as much time as we could by the pool before checking out. Since we had our luggage along, we spiced up the public transit plan by taking the local trolley from outside our hotel to Whalers Village. From there, we bought one last round of The Bus day passes to head to Lahaina’s Wharf Cinema Center, transferring to the bus that would take us on to the Queen Ka’ahumanu Center in Kahului and our next set of adventures.
How Much We Spent (and Saved)
Let’s take a look at the Travel Hack Recap spending breakdown for this leg of the trip:
| Category | Budget | Actual | Notes |
| Flights | $22.40 | $22.40 | $5.60 per person per flight (MSP-SJC, SJC-OGG) + 34,307 Southwest Rapid Rewards miles. |
| Hotels | $0.00 | $0.00 | 75,000 Hyatt points (and no resort fees!) |
| Food/Drink | $345.00 | $299.06 | All the happy hour deals |
| Entertainment | $0.00 | $0.00 | |
| Transportation | $149.00 | $100.13 | The Bus saved The Spreadsheets |
| TOTAL | $516.40 | $421.59 |
Not too shabby considering the two unplanned Lyft rides on the front end. The cash price of MSP-SJC was $268/person and SJC-OGG was $219/person. One night at Hyatt House San Jose Airport would have cost $125.70, and the Hyatt Regency Maui was going for over $500 per night at that time, with a total savings of $1,548.43. Even excluding the savings of taking public transit instead of Uber/Lyft/Taxi/Rental car, and just being generally aware of happy hour pricing, we saved over $2,600 by travel hacking this leg of our trip to Hawaii.
Conclusion
Holy smokes. What an incredible start to a trip we had been dreaming of for years. And despite the travel delays, we still came in well under budget to boot! The cash price of the Hyatt Regency Maui is a little steep for what we like to pay, but it’s an incredible value if you’re able to pay with points. Doing just a little research can allow you to experience all the great food/drink/entertainment you want at just a fraction of the normal price. That’s the beauty of travel hacking!
Have you ever been to Hawaii? Anything in West Maui that we missed? Feel free to comment below!
