4 Weeks In Hawaii: An Intro

After 6 years, 11 months and 5 days on the road on a nonstop 50 state road trip, Shae and I landed on the island of Kauai in Hawaii on December 5, 2024. That was a pretty special moment as it meant we’d finally visited all 50 states.

That was far from being the end of the road trip though. We were about to spend four weeks in Hawaii trying to see as much as we could, while also relaxing and enjoying our time there.

Spending almost an entire month in Hawaii could clearly get very expensive very fast, plus there’s obviously a lot of logistical planning involved. Before we start posting about what we actually did in Hawaii, I wanted to share how we planned it all.

Which Islands We Visited

We spent a total of four weeks in Hawaii, with one week on each of four islands – Kauai, Maui, the Big Island and then finally Oahu.

How We Got To & From Hawaii

I was fortunate to earn a bunch of Southwest Rapid Rewards points in early 2024 via credit card referrals. As a result, that – and the fact that I’d already earned quite a few points from the signup bonus for the Southwest card in the first place – meant that I earned a Companion Pass.

In case you’re not familiar with the Southwest Companion Pass, if you earn 135,000 Companion Pass-qualifying points in a calendar year, you earn the Companion Pass. This allows you to select a partner who’ll travel with you on a Southwest flight that you’re taking and they fly for free, other than paying for taxes and fees. That’s the case whether you’re booking with cash or Rapid Rewards points.

A couple of years ago Southwest started flying to Hawaii, so I initially booked my flight to Kauai from Phoenix using Southwest points, then booked my return leg from Honolulu to Phoenix using those points too. I was then able to book Shae’s ticket for free other than the $5.60 in taxes and fees in each direction.

That was a pretty good deal, but we ended up changing our plans. Our original intention had been to fly from Phoenix as there was a pet-sitter there we wanted to use. However, our friends in Denver offered to look after both Truffles and our car while we were away. That meant we needed to get from Denver to Phoenix for the start of the trip and then from Phoenix to Denver at the end of it. Due to flight times, this also meant needing to book a hotel in Phoenix.

That was going to be a lot of hassle. Denver is one of United’s hubs, so when I found a nonstop flight from Denver to Kauai for a somewhat reasonable number of United miles, I booked that and cancelled the Southwest flight and got those Southwest points back.

I then kept an eye on the pricing for United’s nonstop flights from Honolulu to Denver for our return leg. At one point the prices dropped significantly, so I waited to discuss it with Shae the next morning (this was late at night), but by the time I came to book the prices had jumped back up. They dropped again several weeks later, so I jumped on that opportunity and booked those flights.

On the one hand it wasn’t as good value as the Southwest flight because the Companion Pass meant Shae’s ticket would’ve been free, but being able to book a nonstop flight was more appealing, as was the flight timing. As it turns out, the timing worked out even better than expected. It got us back to Denver 1.5 days earlier than we would’ve gotten back if flying Southwest via Phoenix. That enabled us to outrun the winter storm that hit in the first week of January upon our return – otherwise we’d have gotten stuck in Kansas City or St Louis.

We had quite a large balance of United TravelBank Cash, so it was nice to get to use some of that as it expires after five years. I also have Silver status with United, so that meant we were able to get upgraded seating in both directions.

How We Flew Around The Hawaiian Islands

If you want to island hop in Hawaii, you have two main choices – Southwest and Hawaiian Airlines. Prices for our dates were pretty much the same across both airlines, so we picked Southwest for all three of our inter-island flights for a couple of reasons.

One reason was my Companion Pass. That meant I was able to book my ticket using cash or points, then add Shae for only $5.60, thereby pretty much halving what we’d have had to pay with Hawaiian Airlines.

The other benefit of flying with Southwest was that they offer two checked bags free. Seeing as we were going to be in Hawaii for four weeks and were bringing along Christmas gifts as we were visiting in December, we each had two checked bags, a carry-on each and a personal item each. With Hawaiian we’d have had to have paid for all four checked bags on three separate flights, greatly increasing the cost of that option.

How We Booked Our Accommodation

Accommodation in Hawaii doesn’t come cheap, especially when you’ll be there over Christmas and New Year. Thankfully hotel points came to the rescue.

I started planning our accommodation about nine months in advance. Honestly, I should have started even earlier – a year ahead of time probably would’ve given us even more options, but things had been so busy that I put it off until we were in Idaho in March.

Kauai

The first hotel booking I made was a week in Kauai at the Grand Hyatt Kauai. That’s an incredibly popular resort for people with Hyatt points to stay at as it’s such a beautiful property with great amenities, excellent service, a club lounge and more. Many days in December were at peak pricing when using points, but by booking a stay for the second week of December we only had to pay the standard pricing of 25,000 points per night.

Big Island

The Big Island didn’t have any hotels bookable for a reasonable number of points based on the points we had, but thankfully we had an alternate option.

Wyndham has a partnership with Vacasa which allows you to book vacation rental properties using Wyndham Rewards points. I found a decent-looking rental in Kona which only cost 15,000 Wyndham points per night, so I called up to make that booking. I have a Wyndham Business credit card which gives a 10% discount on points redemptions, so that ended up only costing us 13,500 points per night.

Maui

A few days after booking our accommodation for the Big Island, I booked our stay in Maui. Once again we used Hyatt points, this time for a week at the Hyatt Regency Maui. Seeing as this was in the middle of December, we were able to book most of the nights at standard award pricing of 25,000 points per night, although the final night was 30,000 points as it was at peak pricing.

However, a couple of months later I made a change to that reservation. We wanted to drive the Road to Hana and stay a couple of nights at a hotel in Hana, so I booked two nights at the Hana-Maui Resort using Hyatt points for our first two days in Maui, then booked a five night stay at the Hyatt Regency Maui. After ensuring those bookings were locked in, I cancelled the week-long stay at the Hyatt Regency Maui I’d originally booked.

Oahu

Our final booking was for Oahu. I’d made all the previous bookings in March, but I procrastinated with Oahu as I couldn’t come to a decision as to where to book in Waikiki. There were actually too many options to choose from, each with their pros and cons. A Hyatt Place was tempting as it was in a good location, but we were already redeeming a ton of Hyatt points for the stays in Kauai and Maui, so I wasn’t keen on redeeming a further 100,000+ Hyatt points for Oahu.

There were several Vacasa options bookable with Wyndham points, but I waited too long and they either got booked up or became more expensive which put them out of the allowable price range when using Wyndham points.

Thankfully the Wyndham points still ended up being useful. There was a timeshare property in Waikiki that was bookable with Wyndham points. That was a studio suite with a full kitchen and lanai which only cost 15,000 points per night, or only 13,500 points per night courtesy of that 10% discount I mentioned earlier.

How We Got Around The Islands

When we first started planning our 50 state road trip, we’d looked into how much it would cost to ship our car to Hawaii at the end of the road trip. This was something we were really keen on as it would mean that our car would be one of probably only a handful of vehicles to have ever driven in all 50 states.

Back in 2017, the research I did suggested it would cost ~$1,000 to ship it. That didn’t sound completely unreasonable, especially because it would save us the cost of a rental car on whichever island we shipped it to. The plan was to then sell it in Hawaii.

COVID foiled those plans. Ever since 2020, there have been supply chain issues all over the world, increased shipping costs, inflation, etc. When looking into the cost of shipping our car to Hawaii closer to our time there, it looked like it would cost $3,000+. That was a much less viable option, especially because we figured it’d be useful to still have a car to drive back across the US afterwards!

That meant our car stayed in Denver with our friends, only making it to 49 states + Washington D.C. Leaving our car behind did mean we needed transport on each of the four islands though.

For Kauai and Maui, we rented a car for the entire week on each island. Our time on the Big Island was over Christmas, so that jacked up the cost of rental cars. Renting a car for a week was going to cost more than $1,000, so instead we booked a Turo for three days for ~$350 at the start of our time there, relying on Uber rides for the other few days.

That left our week in Oahu. We knew we wouldn’t need a car for the entire time, so we ended up renting a car for one day, then rented a car for two days at another point, using Uber to fill in the gaps. If we’d have been able to get free parking during our time in Waikiki, it might’ve made sense to just book a car for the entire week. However, parking would’ve added something like $50 per day, so it wasn’t worth paying that additional amount.

Why Didn’t Truffles Come To Hawaii?

I mentioned earlier in the post that we left Truffles with our friends in Denver while we went to Hawaii. We were sad about our car not making it to all 50 states, but we were even more sad that Truffles didn’t make it there too.

Unfortunately, bringing Truffles with us just wasn’t a viable option. If we were moving to Hawaii, of course we would’ve done everything necessary to bring her with us. The problem was that taking your dog to Hawaii isn’t like flying with them to any other US state – it’s like taking your dog overseas due to Hawaii’s strict rules regarding animals being brought on to the islands.

That meant there were a lot of restrictions regarding her needing to have various vet visits and certificates and I think it still might’ve included a quarantining period in Hawaii. Cost was another massive factor. Taking into account our flights to and from Hawaii and our inter-island flights, it would’ve cost us ~$750 in pet fees to bring her on board.

Having Truffles with us on all four islands would’ve restricted our accommodation options even further, plus there would’ve been hotel pet fees to pay. Not to mention that it would’ve been hard to do all the activities we wanted as many wouldn’t be pet-friendly.

After doing some initial research, it was looking like it would cost $1,500-$2,000 overall to bring Truffles with us which was very steep. That’s why we were grateful when our friends were happy to look after her while we were away.

Ultimately, I think Truffles was probably happy about that too! I doubt she’d have enjoyed all of those flights being in a crate, nor having to be left in a hotel while we went off doing stuff that wasn’t pet-friendly. Not to mention the fact that she got to have all kinds of adventures with our friends, from going out to see Christmas lights to getting her photo taken with Santa at Bass Pro Shops 🙂

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So that’s a little bit of background about how the logistics worked for our time in Hawaii. Next up – all the fun stuff we did in Kauai!