Trip report: Maui and Honolulu
Thought I’d share a credit card churning/points based trip report for a common destination amongst churners: The islands of Maui and Oahu, Hawaii.
This post is so long- sorry in advance for those who want to quickly scroll past.
Travel
Myself and husband, 43, daughter and niece, early 20s and our younger kids, 7 and 11, known as “the lils”
Did pre-departure testing in a drive-through Walgreens pharmacy. Readily available appointments and super easy self-administered rapid test nasal swab. Results were ready in about 2 hours, sent to my email. Uploaded these to Hawaii’s safe travels portal and filled out their other entry forms. No cost for testing through Walgreens- they don’t even request insurance information.
Paid for most of our trip from Chicago to Maui utilizing Southwest vouchers we’d received for shifting us to a different flight to accommodate open middle seats. A few months prior to our departure, Southwest scrapped our return flight, so we booked Alaska Air for the return. 6 of us flew economy for both flights. Our Southwest flight was at 6am, requiring a 3:30 am exit from our home. The early departure made it possible for us to sleep on the plane. We upgraded our boarding for four of us, utilizing a Chase Southwest card which has this benefit. Otherwise we were in B boarding on a fairly full flight. Upgraded boarding got us A5-9. I’ve never done this before, but I packed a ton of food in a small cooler for the flight (frozen cheese and sausage, crackers, fresh tomato, basil and French baguette). Boy was I glad I did, because there wasn’t a single thing open at Midway prior to our departure. This fed our group well during the flight and it felt filling without being greasy, overpriced airport food. Southwest served assorted beverages (can if requested) and snack packs on each leg (Chicago-Oakland-Maui). I’m sure you’re asking how we could manage 9-10 hours of flight time on Southwest? Honestly, I’m a former airline crew member, and so it’s in my blood to be on flights for 20 hours at a time, standing or sitting on a thin bench. With six of us usually traveling, it just doesn’t seem feasible to find first class award seats. As our kids get older and we travel in smaller groups, I’m sure that will be in the cards. TIP: If you have time between flights, Southwest is pre-clearing you for Hawaii entry. They check your safe travels account and pre-screen you, providing you with a wristband. The wristband allows you to walk out the doors when arriving in Hawaii. Our connection was too tight to get in this long line, so we did this in Hawaii. Most people were pre-screened, so our wait was maybe 10 minutes and we were out the door to car rental.
I love Maui’s open air terminal. We only ever travel with carry-ons now, so we were straight out to the mini-tram to the car rental station. We waited about 30 minutes in the Hertz/Thrifty/Dollar line and another 30 minutes in the lot for a car to be provided to us. Having heard some horror stories about Hawaii entry right now, we were really pleased with this. Paid $335 for a 6 day mini-van (provided an Escalade- yay) through Orbitz, which was a great price considering how expensive car rentals are now. I had ordered drive-up pickup from Target in Maui near the airport, so we stopped there and picked up some limited food essentials and sunscreen/bug spray and a $20 booster seat.
For our first five nights we were staying at Waldorf Astoria’s Grand Wailea. While we are low-budget on flights, we are bougie with accommodations. I have learned that I am not a “I can stay anywhere” type of person. We had two rooms at GW, 5 nights each, so a total of 10 nights. I was able to get 5 nights on points, 1 FNC and four nights paid. 3 of those nights were a Hilton price match to an Orbitz/Expedia price. Hilton cash rate is about $900 with taxes and fees. Check in was long, but they upgraded both of our rooms to ocean view from terrace view due to my Diamond status and made it so that we wouldn’t have to check in/out or move rooms with our MANY, MANY different reservations. I received Diamond status by getting the Hilton Aspire Amex prior to the trip, which also provided a FNC and $250 credit at a Waldorf Astoria resort. The $250 resort credit was basically eaten up by the $45/nt self-parking fee. The points were a combination of the Hilton sign up bonus points 140k and MRs transferred 1:2 plus 40% transfer bonus during a transfer bonus period. Here’s the best part: In addition to upgrading both of our rooms, they also provided Diamond breakfast benefits for both rooms, which was $40 for each room to be used at their quick service or table service breakfast restaurant. Despite the fact that Maui food prices are INSANE ($15 for an Açaí bowl or egg/sausage breakfast croissant), the $80 benefit served our entire family a hearty breakfast each morning at the quick service restaurant. Don’t you love when you fall into a new routine on vacation? Breakfast at the quick service restaurant was our routine, and it was a lovely start to our day.
The low-down on Grand Wailea. Yes, the rooms are dated. The bathroom is huge, which is a nice plus. Everyone raved about the pools before we arrived, but I really couldn’t understand what the fuss was about until we got there. I think there are at least 7 pools, starting on an upper level and cascading to the lowest level. They are each connected by a short distance water slide. The second to final water slide leads you into a rapid type lazy river, which floats you along to the final water slide. The final water slide is a multi person side by side slide, which leads you to a calmer lazy river. That then leads you to the main activity pool, as well as baby sand pool. There’s also a Tarzan rope swing pool and a scuba dive training pool, as well as two slides which take you from the top of the activity pools down to the bottom. The activity pools (slides and Tarzan swing) were open from 10:30 am-5pm). The only thing closed was the water elevator. I can do about 90 minutes in the pool, and then I’m usually just there because my kids love it. But at GW, it was actually SO MUCH FUN to be in the pool. The water temp was great and the pools were so entertaining. I’m afraid my lils are going to be disappointed with any other hotel pool in the future!
So here’s the negatives. You have to reserve pool chairs at 4pm the night before using their online portal. Except it NEVER works. It typically just spins and drops out. Then, each morning, you have to wait in a line 10 families deep to get wristbands and your pool towels and beg for pool chairs somewhere. Most mornings they were able to accommodate us poolside, at the beach or in grass chairs. Also, service shuts down at 5pm. So no pool attendants, no ability to get a towel without going to reception. For a resort which charges $900/nt for a room, it’s not acceptable to have such poor of an IT reservation system or not to be able to get a towel past 5pm. Also, GW is a BIG resort which takes about a day to get your bearings.
Other positives about Grand Wailea: There is an absolutely AMAZING beach path that passes through all of the Wailea resorts. It is so, so picturesque. You can even catch glimpses of different luaus at various resorts, if you are into that. We saw so many birds, stray cats, roosters, etc. One day, as we walked past the Four Seasons, one of the landscaping team members noticed our sandy feet and gave us a foot shower with his hose. He asked us where we were staying and encouraged us to stay with Four Seasons in the future. When you have that kind of service from your entire team, you are doing it right! Back at GW, we enquirer about cultural activities, like lei making, hula or ukulele lessons. They put us in touch with their Cultural Director, and she arranged a morning session for just our family, where she taught us hula and ukulele. This was a highlight for my kids and I felt like they left knowing more about Hawaiian traditions and culture. This was included in the resort fee and I believe they normally provide a calendar of events, but due to COVID, they are doing this by request right now. GW provided a 1:30pm late checkout for both of our rooms. Their concierge team was great about answering requests by text- love the digital age.
I assume the only readers left on this looooong post are those planning a trip to Hawaii, so I’ll keep blathering on. Outings:
Road to Hana. We spent half our time on the resort, and half our time self-exploring. We did Road to Hana one day and utilized the Shaka app ($14.99 per tour or $30 for the 6 tour bundle. TIP: You want the bundle). This app was a trip highlight. You download the “tour” in advance and then the app uses GPS to determine your location. We named our tour guide Alfie, and he told us exactly what stops were coming up, where to park, if it was worth stopping, etc. I was REALLY nervous about doing Road to Hana because of the 600+ curves, narrow cliffs and 59 one-way bridges. But it really was manageable and it was a great day. We purposely got a late start (9:30 am) and did halfway to Hana. It was perfect for our family. We saw and swam in beautifully frigid waterfalls, stunning coastal views and ate roadside banana bread from Auntie Sandy’s. We only had one hairy experience when we came around a blind curve and were face to face with a Mack truck. We were able to reverse until we could find some shoulder and he passed. The Shaka app was so great to tell us some Hawaiian history and interesting stories along the route. I hear the Road to Hana is also called the Road to Divorce. Do yourself a favor and get the Shaka app! He does all of the navigating for you.
Lahaina. One afternoon we went to the Village of? Lahaina. We explored the huge Banyon Tree, shopped, got dinner and of course, shaved ice. The 20 somethings really liked this area’s surfer vibe.
West Maui Coastline Tour. Again, we used the Shaka app and downloaded the Coastline tour. We didn’t plan to do the whole circle, so we modified it a bit to our needs. Alfie is great because he just picks up where you are at. We went to the Iao Needle and wow is this a beautiful valley. Lots of stairs which made it clear I am out of shape. From there we looped around and stopped at an overlook to see if we could see any whales (probably too late in the season) and stopped at Leoda’s Kitchen & Pie Shop and General Store. Leoda’s Kitchen & Pie Shop had hands-down the best food we had in Maui. HUGE portions. The General Store had good prices as well for souvenirs. And Leoda’s has a REAL bathroom. There are great swimming beaches along this route. From there we went to Dragon’s Tooth Trail and the Nakalele Blowhole. For me this was our toughest excursion. The landscape changes to sheer cliff dropoffs and hairpin turns. I understand past the Blowhole it gets much worse. Our adventure was plenty for me and we headed back “home.” The blowhole was the highlight for my 20 something niece.
Overall, we found Maui to be incredibly beautiful. Just jaw-dropping scenery. And just about every excursion we did was free, or the cost of a state park admission (think $10). Food prices are up there ($23 for a burger in some places), but it IS an island. We really liked the Wailea area and would return there again if we ever visit again. We took a 23 minute inter-island flight to Oahu, which doesn’t require any additional COVID testing. Flew on Southwest again and this was a really pretty visual tour. We saw the Island of Molokai from the air and WOW, is it beautiful.
Honolulu, Oahu. We stayed at the ‘Alohilani hotel on Waikiki beach, paid cash through Orbitz, about $250/nt/room plus taxes/resort fee. The reception staff upgraded us to ocean view and Diamond Head/Ocean view. Arranged for SUPER late checkout at 8pm for a $225 fee for one room prior to our 10:30pm red-eye flight. We primarily came to Honolulu to see Pearl Harbor. We were able to get reservations both 7 days in advance and extra ressies a day in advance for the USS Arizona memorial. A heavy outing AND we left with so much gratitude. A service woman answering questions on the memorial was asked what three questions did she wish visitors would ask (great question, right?). The final thing she said, and what every American should take away, is that “freedom isn’t free.” We have the privilege of freedom because of the men and women AND THEIR FAMILIES who serve our country. We should endeavor to do our best to never take our freedom for granted.
My daughter and niece hiked Diamond head. Other than that we had pool time (the pool was FRIGID) and enjoyed ‘Alohilani’s beautiful 5th floor pool deck and lounge. We were there for Easter and they had Easter eggs in the lobby and an egg decorating activity. This hotel also has a really great activities schedule worth checking out. There were great dining options right onsite. I would recommend this modern hotel. We used Uber/Lyft for transportation in Oahu. There’s a real shortage of Uber/Lyft drivers, attributed to how cautious it seems many on the Hawaiian islands are. We even had the same Lyft driver twice, which has never happened, anywhere.
Overall thoughts on Honolulu: In a few words, it’s not for us. It’s busy, overcrowded, there’s a homeless problem which understandably stems from substance abuse or mental illness, often. I’ve never worried about stepping on a hypodermic needle on any beach, but I did there. Our expectations were low going in, so it wasn’t a surprise. Two nights there were plenty and I don’t envision us returning.
Our return red-eye flight was on Alaska. I status matched to their highest elite level from Frontier or Southwest. This got me early boarding and a chocolate (I’m fancy now), as well as the ability to move my entire party up to their elite section of the plane. While this was the same seat category, as our aircraft was shuffled, we’d ended up in the last row (non-reclining). So at least elite status got us out of those terrible seats. Any minor entitles you to early boarding, which we utilized for this full flight, mostly so we wouldn’t be forced to check our bags. We paid cash of $235 per one-way ticket, so rather economical.
Overall impressions. Our last four trips have been to FL, FL, FL and FL due to the pandemic! So it was great to get out into the world again, and it many ways it felt like an international destination. We thought the weather was perfect: hot enough to enjoy the pool/beach, but the trade winds kept you cooled down. If we return again, it would be to Maui/Kauai and maybe Aulani, because, Disney. I’d love to see sunrise at Haleakala, explore upcountry’s lavender fields and goat farm, snorkel the Molokini crater, as well as whale watch. Our hesitation to return would be probably because to the long flight times from Milwaukee/Chicago. There’s so much European travel to do for the same flight durations, that we could see Hawaii falling in more of a 5-10 year rotation for us. And ideally a red-eye, nonstop flight. Maybe even lie-flat seats, some day.
This will be our first time redeeming any points, and I cannot wait! We chose to save the Arrival + for the Disney vacation because it is way better to redeem those points for travel.
I’ll just be super happy if it at least resets my miles expiration date.
I'm 0/24 at this point and P2 (who is much more active on disboards) is 1/24. I had her get the CSP for the 80,000 point bonus last year, thinking it was too good to last (ha!). P2 has mandated layovers are not viable due to our kids issues with airsickness. We will be travelling out of a AA hub with direct Orlando flights from SW and Frontier, I'll be focusing on SW due to the few choices for transferring points to Frontier. We'd be staying onsite. Our normal monthly spend is about $2,000. We don't own a business or have any side-hustles that could be converted into a business.
