With three days of tropical lounging under our belts in West Maui, we were ready to set out on the busier part of our Hawaiian vacation. Since those first three days were a late add-on, our itinerary from here on out was jam-packed with the more touristy activities associated with the island – Road to Hana, anyone? Would this be where the travel budget was blown? Check out my Travel Hack Recap of Hawaii – Sightseeing & Wailea below!
To read Hawaii, Part 1 – The Backstory, click here.
To read Hawaii, Part 2 – West Maui, click here.
Where We Went
From the Ka’anapali area of Maui, we bus-hopped our way back through the central lowlands of the island and northward to the town of Kahului. Since this was the regularly scheduled portion of our trip, it was basically a reset: back near the airport, picking up the rental car, and preparing for the legendary Road to Hana the following day.
Day 5, continued – Ka’anapali & Kahului
Because our original flights weren’t supposed to arrive in Kahului until late at night, we scheduled our rental car pick up near the airport similarly late. So we had some time to kill.
We took as much time at the luxurious Hyatt Regency Maui as we could, then bus-hopped our way from Whalers Village in Ka’anapali to Wharf Cinema Center in Lahaina, then to the Queen Ka’ahumanu Center in Kahului, before hitching one last bus ride to within a couple blocks of our hotel, the Courtyard Maui Kahului Airport.
Right next to the hotel parking lot, we found a neat gathering of several food trucks offering a variety of local and foreign fare. Unfortunately, the wait time for some of the trucks was 45 minutes to an hour, so we settled for something that ended up being pretty average. We retired to the hotel…while eating our dinner and watching the news, we learned there was a flash flood watch in effect for most of the island, particularly the north and east (windward) side where we were heading for the Road to Hana.
Not wanting to get caught up in a flash flood and swept out to sea, we pivoted.
Day 6 – Iao Valley
Though slightly less optimal and certainly not according to plan, we decided to postpone our attempt at the Road to Hana until the following Monday when the weather appeared to be better and the weekend crowds were not likely to bog us down. Instead, we embarked on our first true sightseeing adventure: the Iao Valley.
It’s worth noting first that we stopped at the Walmart in Kahului for some groceries on our way out of town. The fresh fruit selection wasn’t as bountiful as we were hoping, but the prices were much more reasonable compared to other parts of the island. I was pleasantly surprised to find that 12-pack of Kona in Ka’anapali was less than $15 here, so I grabbed some to keep in our room.
I also have to plug the Gypsy Guide app for guiding our Maui explorations. If you’re interested in some historical and cultural tidbits while visiting Hawaii without the cost of a guided tour, we highly recommend the Gypsy Guide. The app works off of your phone’s GPS, with driving directions and the aforementioned tidbits automatically prompted along the way. The guide also gives helpful suggestions for where to park, what attractions may/may not be worth your time, and more. Well worth the $9.99 price tag for the full Maui tour (apparently $14.99 now), and they have other audio tours in Hawaii, the continental US, Canada, and Australia.
The Iao Valley is an extremely lush region in the west-central part of the island with incredibly steep cliffs, several picturesque streams, and rich historical significance. It’s just a short drive outside of Kahului with a state park entrance ($5 per person + $10 to park), and about a mile of walking trails to explore – perfect for our first adventure.
We explored the trails for a bit and then stopped at Kepaniwai Park on the road back towards Kahului. Kepaniwai Park has beautiful gardens and small structures with historical placards dedicated to the various Asian immigrant groups that settled in Hawaii and how they have impacted the region. Pretty cool if you’re into that sort of thing.
Having successfully completed our first Hawaiian expedition, we hopped back in the car and followed our narrated audio tour south to Wailea, our home for the next five nights.
Day 7 – Wailea (Luau Day)
For our five nights in Wailea, we stayed at the Residence Inn Maui Wailea. We booked with Marriott points, which included the fifth night for free, so all we had to pay upon checkout was for parking the rental car. It’s not the super swanky resort right on the beach that most tourists prefer, but much more affordable and within walking distance. A selling point for me knowing the cost of groceries in Hawaii was that breakfast was included – though with COVID restrictions, that turned into a less attractive grab-and-go situation.
After a morning spent snorkeling at Ulua Beach, we returned that night for the main entertainment attraction of our entire trip: a traditional Hawaiian luau at the Wailea Beach Marriott.
The luau performance was spectacular, and there was more than enough food to stuff ourselves full (and an open bar). Due to COVID, the tables were socially distanced and each party had their own table. So we ended up with an entire table to ourselves, and all the food served family-style to go with it. It was A TON of food but we did our best not to waste much.
Day 8 – Haleakala
If you want to feel like you’re on another planet, make the drive up the Haleakala Crater on Maui. After several miles of switchbacks and hairpin turns, you emerge above the clouds to a totally different landscape than you left behind. It’s recommended to go for sunrise or sunset if you want truly spectacular views, but I’d say just about any time of day is worth it. I’m not usually one to be blown away by nature, but….wow.
Pro tip: the entrance pass for Haleakala State Park ($30) is the same one that gets you into the Pools of Ohe’o at the end of the Road to Hana, if you go that far. Do these two activities within 72 hours of each other to avoid paying the entrance fee twice.
Day 9 – Road to Hana
At long last, we were ready to embark on the Road to Hana. Though it wasn’t quite as optimal as leaving from Kahului as we had originally planned, starting from Wailea only tacked on another half hour or so. We hit the road at about 8:30am, stopping in the town of Paia for a massive acai bowl, and then continuing on the long, winding Hana Highway.
In hindsight, I would leave a little earlier in the morning. There’s limited parking on the side of the road for the various hiking trails, waterfalls, and other scenery, and by the time we arrived there were no places to park. Since our main goal was to get to the end of the road past the town of Hana to the Seven Sacred Pools of Ohe’o, it wasn’t a big deal at the time. But then we hit a major roadblock.
While offering stunning views, the thing about the Road to Hana is that it’s a single, narrow lane in each direction along the edge of a cliff for miles. So when a power line pole falls across that narrow road, traffic STOPS. Like turn-off-your-car-and-roll-the-windows-down-hope-you-have-some-good-podcasts-downloaded-you’re-going-to-be-here-a-while stopped. That’s exactly what happened to us, almost exactly halfway through the drive. After the first hour, we decided to wait it out instead of turning back and trying to make the entire trek the next day. Luckily(?) it was only another hour before the local utility crew was able to clear the road and allow traffic to pass.
Though behind schedule, we made it to the Pools of Ohe’o in time to make some of the hike past the waterfalls, rainbow eucalyptus trees, and to the bamboo forest before turning back. At this point, I definitely recommend the Gypsy Guide, as the narrated audio tour breaks up the drive back to Kahului after a long day in the car.
Day 10 – Last beach day in Wailea
On our last day in Wailea, we soaked up as much beach time as we could. We hit up Makena State Park, just south of where we were staying in Wailea, as the beaches there were expansive and highly rated.
Day 10 – Wailea, Maui to Honolulu, O’ahu
Our final day on Maui began by returning the rental car and heading to the airport for a short-hop flight over to the island of O’ahu. I’ll save those details for the next post!
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 | $0.00 | $0.00 | |
| Hotels | $0.00 | $4.00 | 206,000 Marriott points + 5th night free in Wailea (and a load of laundry) |
| Food/Drink | $300.00 | $235.95 | $46 in groceries, a couple happy hours at Maui Brewing Co |
| Entertainment | $88.00 | $80.70 | Gypsy Guide, park entry fees at Iao Valley, Haleakala, Makena Beach + 27,833 Chase Ultimate Rewards points for luau |
| Transportation | $195.00 | $120.55 | Mostly hotel parking, gas for rental car + 33,476 Chase UR points for rental car itself |
| TOTAL | $583.00 | $441.20 |
Very impressive streak of under-budgetness we have going here. The cash price of one night at Courtyard Maui Kahului Airport was $253.18, and five nights at the Residence Inn Maui Wailea would have cost $2,785.92 at that time, not including parking. We also saved some cash by redeeming Chase points for the rental car (33,476 x 1.25 = $418.46 value) and luau (27,833 x 1.25 = $347.91). Even excluding the savings of taking public transit instead of Uber/Lyft/Taxi/Rental car, and again taking advantage of happy hour pricing, we saved over $3,800 by travel hacking this leg of our trip to Hawaii.
Conclusion
We really got into the swing of island life during this leg of the trip and packed in plenty of touristy exploration as well. Hotel points saved us big time in out of pocket costs. And really, how much time did we spend at the hotel? Definitely not enough to splurge for the big fancy resorts on Wailea Beach, in my opinion. 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!
What part of our trip so far interests you the most? If you’ve been to Maui, what were your favorite parts? Feel free to comment below!
