Sunday
We emerged from our flight in Honolulu (I managed to get some sleep thanks to the upgrade Virginia insisted on) and thankfully had an easy passage through passport control and COVID check with our PCR test results at the ready. We then headed over to our next flight, a very short one to Maui.
Once we arrived, we needed to get our rental car for the next few days. Virginia’s status with Hertz meant we could take our pick from the President’s Circle row, which oddly had only a couple of vehicles: an SUV and a Mercedes-Benz SLC 300 convertible. It was us with our backpacks and an older couple with multiple roller bags looking at these two cars. The other couple almost ran for the SUV, leaving us with the car we’d have wanted anyway — who wouldn’t want to drive a Mercedes convertible in Hawaii?!
Especially when the first order of business was taking the Road to Hana to get to our first hotel, the Hana-Maui Resort. It’s “only” 50 miles (80 km), but takes at least two hours to drive. The two-track (one lane each way) road is full of switchbacks and hairpins through the Maui forest. That means the traffic is a mix of locals who just want to get where they’re going, tour buses, and tourists (like us) with a variety of driving capability and confidence. We went around our share of tourists and buses, and definitely got passed by locals during the drive. Incidentally, this drive was why I was upgraded on the flight — I definitely needed to be alert.
We checked in at the Hana-Maui Resort, which is beautiful and dates back to before the chain hotel invasion (even if it became part of the Hyatt system in 2020). We were upgraded to an ocean view, which was beautiful to watch as the ocean hit the rocky shore. We did that for a while before getting hungry. Hana is far enough off the beaten path that food options aren’t expected chains. Instead, we purchased wine at the general store and chicken pad Thai and chicken basil stir fry from Ae’s Thai food truck, and enjoyed all that outside.
Monday
We were up early, so we walked to My Tita’s coffee stand for coffee and banana bread. After getting back to the room, I set up a laptop for interviews for a job I was in late stages for. (I know, this was a vacation. But I figured there were two advantages to scheduling interviews during vacation: (1) I wasn’t on my usual busy and stressful schedule, and (2) I could schedule them for 8am, interview for two hours, and then I had the rest of the day in Hawaii. It all worked out and I got the job, so no regrets.)
After the interviews, we had a hot breakfast, splitting a Loco Moco plate. We still had some banana bread from the morning, deciding that would be a great afternoon snack. So we headed outside, even though it was a rainy day (pretty common as Hana is on the edge of the forest). We picked up some wine at the general store and got takeout — shrimp and fish tacos — at Makai cafe. We took food and drink back to the room to find our banana bread was overrun with ants! So we tossed that (in a bin outside our room), ate, and relaxed the rest of the day, getting dinner from the hotel.
Tuesday
Time to head out for the next part of the trip. So we packed up and had a hotel breakfast (by the way, all the food was quite good) before getting in the car. We took the same road back west toward Lahaina, stopping in Paia for a snack and coffee at Better Things. Once we got to Lahaina, we made our way to the Hyatt Regency, which was both where we were staying overnight and where we could return the car. After two nights in Hana, the resorts in Lahaina seemed over the top. We mostly enjoyed our room and its balcony, leaving for sushi and sparkling wine at Japengo. After dinner, we watched a little of the nightly luau presentation from our balcony before going inside for the night.
Wednesday
The main part of our Hawaii trip starts today as we head from Maui to Lana’i. We had breakfast at the Regency Club (sadly the coffee was not good, which is especially sad in Hawaii). We made our way to the ferry in Lahaina and took it across to Lana’i — an hour-long trip during which I got a little queasy. But we got there okay and were taken up to the Sensei resort, which is interestingly not on a beachfront. Frankly, that made it more enjoyable because it was quieter than its sister resort at the beachfront. Not gonna lie — this was an extremely opulent experience for us.
We had lunch at the bar (chicken and shrimp mini-tacos with champagne and cocktails) and walked around the resort to get oriented before getting to our room. We chose room service, getting miso soup, quail, kohlrabi salad, roast chicken with vegetables and wild rice, with a bottle of Schug Pinot Noir 2018.
Thursday
I woke early and joined a morning stretching class, which felt great. We had breakfast (smoked salmon and eggs with French press coffee) in the room and relaxed for a bit. We went to the beach resort twice: first for lunch at Malibu Farm and some beach reading, and then again for dinner (after going back to Sensei to change) at Nobu. I failed to take any notes on dinner, but remember both the food and service was excellent.
Friday
I had two more interviews that morning — same setup as before. After those were complete, we walked into town for lunch at the Blue Ginger Cafe, which was mostly populated by locals. We then had coffee at Coffee Works before walking back to the hotel to change for the evening…
… which was a sunset cruise! In addition to it being beautiful on the water, we ended up talking with another couple, Michael and Stephanie, who were also staying at Sensei and live in the same part of the world that we do. We had a great conversation on the boat, which we then continued into drinks at the hotel bar before calling it a night.
Saturday
After breakfast, we spent most of the day outside. First we joined a beautiful hike along the ridge line, from which we could see the Pacific.
After that, we had lunch before taking a soak in a small private pool. We cleaned up for dinner, which was at Sensei by Nobu on the resort grounds.
Sunday
It was our last day in Hawaii and we were determined to make it relaxing. So we eased into the morning before walking into town for lunch, which was an enormous amount of poke from Richard’s Market that we ate in the central town park. After getting back to the resort, we checked out and were taken to the local airstrip for a hotel-arranged private plane back to Honolulu (opulent to the end, though it’s not like the plane was a Gulfstream jet or anything like that). Once we landed, a car took us over to the main terminal for our overnight flight to DFW. Thankfully we were upgraded and could lie flat to sleep.
Monday
We both worked from the Hyatt Regency at DFW for the day, which meant we didn’t fly home to Chicago until late afternoon, arriving late in the evening. Not exactly the most relaxing end to such a trip but ultimately was a better experience than if we’d tried to go home directly.
record of m. 
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