Nine Nights in Maui for $16.80

Introduction

In this trip, I flew to Hawaii, spending nine nights in Maui before returning to Ohio. For me, this was really a trip of first, and helped build my confidence in traveling on points and miles.

• First visit to Maui.
• First big points redemption.
• First lie-flat business.

Expenses

Ignoring food and ground transportation, the cash component of the trip was less than $20, with the rest covered by points.

Lodging

There’s no better way to book Hawaii than via Vacasa with Wyndham. It’s just 15,000 Wyndham points per night for one “official” bedroom, and this includes many places with multiple sleeping areas such as lofts. Unlike major hotels, you can usually find availability just a few weeks out.

After the 10% discount from my Wyndham Business Earner credit card, I got this beautiful bedroom + master loft for just 13,500/night for nine nights. At the time, the cash rate, including all fees, was just under $500/night.

Flights

While there are many great ways to get to Hawaii, I had a mountain of American Airlines miles from playing the American Airlines Loyalty Game. A quick search via SeatSpy revealed plenty of availability in lie flat business on ideal dates.

• 55,000 miles each way
• ~$4000 retail round trip

Overall, my first lie flat experience was great and it’s going to be very hard to go back to economy.

I should note, there are cheaper ways to fly to Hawaii in business class, but they can be harder to find and book, require positioning flights, and may have reduced availability. A lot of people would argue I should have saved the AA miles for QSuites or higher value bookings. However, this was my first major flight redemption and it was super easy.

Car Rental

When it comes to renting a car, Hawaii has lots of choices. You have the main agencies like Hertz, National, and Budget. Then there are smaller ma and pops like Maui Mini Go where you can get more unusual cars like a Mini Cooper. Lastly there’s a ton of folks on Turo renting out their own cars or running a mini rental agency.

I was late to the game and went with Hertz, leveraging a 30% cash back offer from the Capital One Shopping portal and using the primary rental coverage from my Sapphire Reserve.

Had I not done that, I probably would have picked the best rate on AutoSlash, which has long been trusted by the points and miles community to find rates significantly cheaper than those directly offered by companies.

Since I have Hertz Presidential status through my AMEX Platinum, they let me pick whichever car I wanted. I unfortunately chose this shiny red Mustang. For reasons that will become clear later, on the Kahekili Highway, I would have been much happier with a compact car like a Mini Cooper.

Maui

Kamaole Beaches

One of my goals in the trip was to get some beach time. There were three Kamaole Beach parks, all in a row, and my condo was across the street from Kamaole III. Usually, when walking into town, I would stroll down through Kamaole I and II. Every night had an absolutely perfect sunset.

All the beaches were very friendly, and some had lifeguards. It was the tail end of whale season, and we could see humpbacks spouting fairly regularly off in the distance. At one point there was a sea turtle out swimming amongst beach goers.

Haleakalā

”House of the sun” in Hawaiian, Haleakala is the eastern volcano on the island of Maui.

The national park at the summit is a very popular destination and has limited parking. If you wish to visit at sunrise, you need to make a reservation and potentially book a tour. They don’t require reservations at sunset, but I imagine it can be very crowded. Even though they were wide and well maintained, roads lacked illumination, and I don’t love the idea of driving them at night.

I chose to go in the early afternoon and only had a brief wait to enter the park. Unfortunately, it was very windy, cold, wet and cloudy, with the clouds all around. This hurt visibility at a site that is known for some of the best views in the country. That said, I was still able to get some nice pictures including a rainbow over the crater.

If you visit the summit, I’d recommend going earlier in the morning as there may be fewer clouds. Dress for freezing temperatures and be cautious of high winds. I would also recommend parking as far from other cars as possible as the 40mph wind can very easily catch an opening door slamming it into the car next door. This happened to my rental, leaving a scratch. Fortunately, the folks at Hertz didn’t care so I didn’t get the chance to test Chase’s primary rental coverage.

Western Maui

I took a day to drive highway 30 around the western part of Maui, passing through Lahaina where the fires struck a few months later. My first stop was at Leoda’s, which is famous for its pies. This was followed by a brief stop at the Kapalua resorts, just to check them out. They were very nice, but felt a bit like a separate world, and I think I prefer staying in Kihei.

My last two stops, before risking life and limb on the Kahekili Highway, were the Nakalele blowhole and the Ohai Trail. At Nakalele, I didn’t have the shoes to hike to the blowhole, down the Acid War Zone Trail (its literal name), so I just enjoyed it from the lookout. In contrast, the Ohai trail was a very pleasant hike along the coast with great views of the sea over lush greenery.

Kahekili Highway

The Road to Hana, on the east side, is the most popular drive on Maui. It’s famous for its harrowing, narrow winding path along the coast, and locals jokingly refer to it as the Divorce Highway for the stress it creates on couples that attempt it.

They just call Kahekili the Death Highway. Listed seventh on DangerousRoads.com, the Death Highway is 21.5 winding miles of two-way traffic on a one lane road with blind turns, sheer cliffs on one side and sheer drops to the sea on the other. Guard rails? We don’t need no stinking guard rails.

With all my energies focused on survival, I didn’t get any pictures during the drive, but the time-lapse video below illustrates all the horrors pretty well. Do not watch it if you have a heart condition.

If you decide to drive the Death Highway, here are a few tips.

1. Don’t do it.
   You’re going to ignore me, aren’t you?
2. Drive the clockwise route.
   This way you don’t have to pass people on the sheer drop side.
3. Take a tiny car.
   You want a Mini Cooper, not a Mustang.
4. Familiarize yourself with the backup camera.
   Because you may be driving in reverse, a lot.
5. Know that driving this road literally may violate your rental agreement.
   And void your insurance.
6. Start with plenty of daylight.
   If the sun sets, you may not live to see it rise.

Hawaiian Food

After surviving Kahekili, I curled up into a ball and didn’t leave the condo for about 18 hours, gently rocking back and forth until the tremors finally subsided. With stress hormones peaking, that naturally brings us around to delicious Hawaiian comfort food.

The three best meals I had on Maui were.

• Leoda’s pies (4th).
• Kitoko’s poke (1st).
• Aquarium Seascape’s Tacos (2nd).

Outside a few institutions like Leoda’s, I would say some of the larger restaurants can be hit or miss while the food trucks are where it’s at.

Aquarium

My last day in Maui, I split my time between the Aquarium and Kanaha Beach near the airport.

The aquarium had all the usual plus great exhibits for sharks, jellies and sea turtles. I also enjoyed the sea worms, lobster and shrimp tanks, and the coral exhibits were colorful and informative.

Kanaha Beach Park

Kanaha park is a quiet beach near the airport, off the beaten path. It’s a great place to go if you’ve got a few hours to kill before your flight out, especially if you’re trying to cram in as much beach time as possible. The park is full of stray cats, many of which are pictured below.

Cost Summary

This was a great, all points trip.

• 110,000 AA miles + $15.60: Business lie-flat round trip.
• 121,500 Wyndham points: Nine night Vacasa stay.
• $463: Seven day Hertz rental.

I ended up getting $243.57 back from Capital One Shopping for the Hertz rental, so the true cost was only around $220. That’s about $100 more than I was supposed to get with my 30% back targeted offer, but then, they’ve also failed to pay out $80 in commissions, so it evens out in the end. This is a great example both of how good these targeted deals can be and how badly they sometimes track.

If I were to do it all over again, I would probably make greater use of public transportation as the lines ran all along the coasts and major roads. Then, if I needed to go somewhere more adventurous, I would either join a tour or rent a car for just one day.