Maui has always been a dream of ours.
It never worked out though. Twice before, we had the whole trip scheduled and had to cancel, once due to Covid, and once because babysitting backed out. This time I held my breath until we landed in OGG, and it worked!
I really wanted to stay in Andaz Maui, so I used
www.Openhotelalert.com to get notified when award availability opened. I had to book 3 different reservations, as availability opened at different times for different days of our stay, and ended up using 295k Hyatt points in total for 7 nights at the Andaz.
I emailed the manager requesting an upgrade to the ocean view suite. She replied politely that they never upgrade to suites and for a view room we will have to wait until check-in. She was able to give us an extra fridge and microwave which would be placed in our room prior to our arrival.
We also booked the Hana-Maui resort for Sunday night, using 30k Hyatt points to book into the basic room, and using a Suite Upgrade Certificate to get the garden view suite. I also tried getting an upgrade to the oceanfront bungalow but was told it would cost $500 a night. No thanks.
For food prep, we took along enough food for most nights. As usual, when DW cooked supper two weeks prior to the trip, she prepared extra portions which we froze in containers we knew would fit into the hot logic. Shabbos food we had planned to order there.
I booked United EWR-HNL in lie flat business using 77k United points per person and paid additional 7k United points for a Hawaiian flight from HNL to OGG in Y. We had some extra United points thanks to the
Denver fiasco . I specifically used United points to link the reservations, so I can have my bags checked through OGG.
For the return I booked Hawaiian first using 130k pp Hawaiian points OGG-HNL-JFK. I had Hawaiian points sitting in my account from previous transfer bonuses.
DAY 1- Wednesday Since flights to Hawaii are domestic, I didn’t have access to the Polaris lounge, so I bought 2 United passes. The lounge itself wasn’t anything major, but it’s always nice to have a comfortable place to sit and fill up with drinks.
Kosher Snacks in the Lounge 
United Lounge On the way to the gate, we saw a United flight EWR to PHL!
While standing in line to board the plane I received a notification that I could check into the hotel. I opened my reservation, which was corrected to one stay, and showed an ocean view suite! I pressed the check in button so hard I’m surprised my phone didn’t crack lol. Unfortunately, it did not allow me to check in as the card on file was locked, so I also took a screenshot of the reservation, showing the upgrade so they shouldn’t be able to take it back.
The seats on United 767-400 were wide, private, and very comfortable. We got kosher meals from Fresco which were surprisingly good! I had also brought along our own food, and we warmed them up in flight using the hot logic. The flight was bumpy and long but sitting in J certainly helped.
Fresco Breakfast 
Fresco Lunch 
Landing in HNL After a long day of flying, we finally arrived in OGG. I reserved a Jeep Wrangler from Alamo, and they told me to take my pick of Wranglers they had. Although I have status with National, I didn’t want to gamble as I really wanted a Wrangler. I did notice when I arrived that the National Executive Aisle did not have any decent cars.
Welcome to Maui We did a quick Costco run and checked into the hotel. The check in guy was super surprised at our upgrade. 😊
We set our alarm clocks for 3am and went to sleep.
DAY 2-Thursday We awoke even before our alarms. Thanks jet lag…
This planned was planned just two weeks out, which meant I had a very hard time getting reservations to Haleakala. I checked the website daily to see if availability opened and had 3 alarms set for 12:00 two days prior to the day we wanted to go. I had the website opened by 11:45, refreshed the page at 12, and snagged my tickets.
Arriving at Haleakala early meant we got a good parking spot at the summit and viewing location. To our luck we were in clouds for 90% of the time. All we saw was clouds. Once or twice the clouds moved for a minute so at least we were able to get some nice pictures. It was still an experience standing in the freezing wet cold waiting for sunrise. Would we do it again? Probably. Did we try again on this trip? Absolutely not. Although we had tickets for Wednesday the following week, we decided against trying again.
I had reached out to Rabbi Mendy Krasnjansky from Chabad regarding a Shabbos package, and he told me they were trying to put together a minyan for Thursday. I wasn’t sure if I would be able to make it back in time, but I did, and it was nice.
After a leisurely breakfast we headed to West Maui. Passing through Lahaina was sad. So many houses there completely burned and so many people were left homeless.
Our first stop was the Nakalele blowhole. It was shooting up water every 20 seconds or so. We didn’t hike all the way down, instead sat on some rocks and enjoyed it.
The next stop was the Olivine pools. The weather was not great, so we didn’t go swimming in it. Even so, it was cool to see what rock formations around the ocean can do.
What happened next, we were not expecting. The top of West Maui highway is both exhilarating and terrifying. TBH, I did not realize that this was that road when I started driving. The sheer number of switchbacks and blind turns makes it one heck of a drive. The views, if you are brave enough to look down, are breathtaking. DW was certain we were going to die on this road and kept her eyes on Waze counting down the minutes to our ETA. While it was thrilling, I am not sure I would do it again. I am sure DW won’t let me… We have no pictures of the drive, because DW made sure I kept my hands firmly on the steering wheel.
We stopped at a fruit stand on the way back We planned to go to the Iao State Valley Monument, but upon arrival realized we did not have reservations. The attendant told us we must do it online, but there was no service there. By the time we got service, we were some distance away and were too exhausted to be bothered. Oh well, gotta leave some things for next time.
We got back to the hotel in one piece, watched sunset from the pools, and went in for the night.
DAY 3-Friday Due to the dateline issue, we were told to keep doraysa on Friday, which limited most activities we wanted to do as we couldn’t drive. The beach was a problem too, with stormy weather and high tides, the beach area was basically non-existent at our hotel. The beach crew told us it’s been like this for a while now, and the area is usually much nicer. We were a bit bummed out by that, but it was too bad. They did offer to put out beach chairs on the lawn for us, but we preferred to take a walk.
Walking along the boardwalk is beautiful. It’s a well-maintained walkway with beautiful views of the ocean. Add to that whale season, we were seeing whales everywhere. A little tip someone told us, look for the boats. If you see a boat stopped somewhere that means, there are whales nearby.
We bumped into a fellow yid on the boardwalk who told us they would be having minyan in the Four Seasons. Chabad confirmed this a little later when they came to deliver our food.
We had planned to go for erev Shabbos massages in Andaz spa, however they called me Thursday night to tell me they did not have a male massage therapist because he called in sick. Since we had scheduled one male and one female, they were going to have to cancel the session. I told them to cancel both mine and my wife’s massage and we went to the Four Seasons spa and were able to book a couples massage there. The ambience was nice there, and they played Hawaiian music for us. It all worked out in the end and the Four Seasons spa was even cheaper than the Andaz
View from the Four Seasons After being rejuvenated, we had a free photo session booked courtesy of the resort fee I didn’t pay
. They were pretty accommodating with all our scheduling changes and the photographer did his job well.
A few minutes before the zman we took the Andaz courtesy car to the Four Seasons for minyan kabalas Shabbos. After davening, it started raining. For Wailea being considered the driest place on Maui, we surely had a lot of rain. It was dark, wet, walk back to our hotel after davening.
The food from Chabad was big portions and very tasty.
DAY 4-SHABBOS Shabbos in Maui was beautiful. We had a nice minyan in the morning, and the walk there was nice. We stopped many times to watch the whales frolicking in the distance. After davening we had big kiddush courtesy of Chabad.
DAY 5-SUNDAY The road to Hana honestly deserves a trip report on its own. There is so much ground covered on that one road, you don’t get that anywhere else. Before the trip, we read through the section on this road in the Revealed book and made notations of which stops we wanted to make.
Based on the recommendations of many DDF’ers we purchased the Shaka guide which was a must. Yes, we could have done it on our own, or with just the Revealed book/app, but this guide was invaluable. Without it we would have probably passed by some of our stops, and definitely would have missed a cool cave that wasn’t in the Revealed book. (To be fair we have the 9th edition and I believe they are up to the 11th edition.)
Although we were sleeping over in Hana, we decided to leave early, as we were up early regardless. We packed up just the stuff we needed for the night, enough food for 2 days and we were off! We kept our room in the Andaz, figuring it’s easier to replenish the points, than waste time and energy packing and repacking. Like this we were able to fit everything into backpacks, which we took with us, to avoid potential thievery.
Our trip started by filling up with gas in Costco, the cheapest gas on the island.
We made our first stop at baby beach, a recommendation one of the locals we met gave us. It was a nice beach, but we were filled with too much energy to sit down and get all sandy.
In the beginning we kept our eyes peeled for the rainbow eucalyptus trees. When we finally spotted them, we pulled over to take some pictures. Shaka guide promised us another stop, but we wanted to make sure to capture their beauty. We also saw quite a few tour buses stop at those trees.
Originally, we hadn’t planned to stop at Twin Falls as the Revealed book recommends skipping it. However, we decided as we have all day to do half the loop to make the stop. It was a nice hike to the falls, which were beautiful. We spent some time there and were happy we didn’t skip it.
They had paid parking on site for $10
Our next stop was the Garden of Eden. It’s an expensive entry $20 per person, and all in all probably not worth it. They had some beautiful plants and trees and magnificent lookout points. There was also a waterfall that I believe is only visible from their lookout point. The coolest thing we saw there was a whale tail slapping the ocean repeatedly. It was from some distance away as we were high up, but besides seeing it, we were able to hear the noise as its tail hit water.
After that we stopped at the Keanae Arboretum. It’s a short walk and along the way there are many interesting, labeled trees. As the Shaka guide promised us there was a cluster of the rainbow eucalyptus trees and much nicer photography availability.
Next up was Keanae Peninsula. It’s a turnoff of the road, where the coast hugs the dead-end street. It was an absolutely striking view.
Next up was Wailua Valley State Wayside. It’s an outlook that is 40 steps up with a view that is worth the climb
After that we drove through Upper Waikani Falls, and just passed it slow enough to enjoy its beauty from the car.
Next stop was Pua'a Ka'a State Wayside. There are restrooms there, plenty of parking and very access from the road. We went into the pools beneath the falls and had fun cooling off after a long trip.
Then the guide told us to stop for a roadside cave. We remembered reading that the Hana Lava Tube cost $30 entry so were super surprised. This lava tube is accessible from the roadside but has the smallest opening I ever saw. It was dark, we had flashlights turned on, but super cool! The exit of the cave is right near the entrance (Its kind of like a U) so we didn’t have to climb it back to get to our car.
We were beginning to get exhausted, so for the rest of the waterfall we just slowed our car down with rolled down windows and took in the beauty like that.
After a very long road, we finally got to the hotel. Our upgrade luck was still playing, as we were upgraded to an ocean view bungalow. As globalists, we also got a $15 voucher to use at pools bar.
The bungalows are nice and spacious, and the view was just perfect. The resort is large so they get around using golf carts. Any time we wanted to go to the parking lot, they had a golf cart come pick us up. The resort grounds are grassy and just so calming. I guess that’s Hana as well. Just a relaxed, calm atmosphere. Im really happy we decided to stop here to spend the night. (Thanks
@PBaruch !) The service was excellent as well, with very friendly staff.
Originally, we hadn’t planned to go to Red Sand Beach, scared off by Something Fishy’s TR. But at Thursday minyan, a local who has been living in Maui for 20 years or so, said the only beach worth visiting is that one. So, we stocked up on bravery and went to hike it. While the hike itself isn’t so difficult, the sand is constantly slipping under your feet making it hard to get a good grip. Additionally, at times the path is so narrow that I had to walk sideways. The entire time I was holding on to the cliff, and praying the rocks didn’t dislodge. The locals however were just zipping up and down the trail, one even carrying a baby. Once we got there, it was beautiful. (I feel like I am being very repetitive here, calling everything beautiful, but it truly is! The entire Road to Hana is a beauty.) Strong word of advice though. The so-called sand is rocks. Wear something on your feet. Being a Sunday, the beach was packed, but we found a little corner, hung out for some time, and made the trek back. In a way the back was worse, because we knew what was coming and there was no beach to reward us after 😉
That hike took everything out of me, so we went back to the hotel, chilled at the pools a bit, and went in for the night. We brought along our hot logics which did an excellent job of warming up supper for us. Having a huge balcony, we ate supper on the balcony watching the ocean.
DAY 6-MONDAY 
Sunrise at Hana Maui Before leaving for Hawaii, we made reservations at Black Sand Beach for 10:30am. Since we kept waking up in the early am hours, we decided to change it to 7:30. They allowed changes for no additional fee. It was an easy path down, with a nice staircase that takes you right to the beach. We noticed a cave on the side of the cliff and decided to explore it. It’s a small cave that goes to the ocean. The waves were coming up right into the cave. I imagine that when the tide rises the cave could be inaccessible.
We met two brothers there who had taken this trip right after college and now that they retired, are recreating their trip. They claimed that when they were here first it was a difficult trek. Maybe one day they will construct a staircase for red sand beach as well! Unless of course the locals just want to keep tourists out.
On the way back from Hana, we went to check out Hasegawa general store. It’s an old-town style shop where you can buy anything. We just got some souvenirs and postcards.
The Wailiu falls were the last falls we stopped by on this trip. They are magnificent, tall falls you can swim in. It was quite a difficult hike down, figuring out a path along the rocks, but some people made it and were enjoying the cold pool.
There was a booth of people there, claiming to be from a non-profit agency dedicated to educating people on these falls. They were very busy raking the leaves and taking pictures for tourists…
We then headed to what was supposed to be the main stop of the day, Seven Sacred Pools. Unfortunately for us, the falls were mostly dry, and swimming in the pools was not allowed. We were debating whether to start the Pipiwai trail, but a guy who just finished the entire trail told us that both falls were totally dry, so we skipped it.
Based on Revealed’s recommendations, we stopped at Laulima Farm Fruit Stand for some fresh fruit. She sells a fruit sampler for $18 with a bunch of different exotic fruits. I ordered it and watched her go to the tree to cut off some fruit for me! Really gives meaning to the phrase “from farm to table”. You can walk down a paved path through the garden and see all the fruits growing. You can eat at the stand, there are many tables, some of them surrounded by bamboo trees giving you total privacy. When she brings you out the plate, she also explains what each fruit is and how to eat it. There were at lease 15 fruits including edible flowers. The fruit plate had some of the most delicious fruit I ever tasted! I had to wait some time for her to prepare it as the stand was quite full, but it was 100% worth it!
Fully satiated we continued driving. After doing the West Maui loop, this was a breeze. The road was bumpy in some areas, making me happy I had the Wrangler. The views on this side of the mountain were the opposite of what we had seen until now. We enjoyed the scenic drive, pulling out by some lookout points.
When we got back to civilization, we went to check out the local Walmart. They have a nice big section of souvenirs, and we spent a lot more money than we should have 😉.
Supper that day was from Maui Kosher Farms. We had planned to eat there, but Mendy called to let me know he is going out of town and can only do pickup. While waiting for the food, we walked around checking out the place. It has real jungle vibes. The food was generously portioned and yummy.
DAY 6-TUESDAY Finally, the day before we were leaving for home, we were doing our first paid excursion. This is the awesomeness of Maui. You can do so much sightseeing with minimal expense.
Having never gone snorkeling before this was definitely on our bucket list. We did lots of research into the various places to snorkels and boats going there. We ended up with Calypso and could not have been happier! The boat is huge, plenty of space with tables at every chair. The staff was attentive, kind and the service were excellent. The boat has lots of ladders for easy entry to the water and 2 slides. With many different floatation devices and 3 lifeguards in the water it felt very safe.
Monday afternoon, I went to take a complimentary GoPro from the hotel, once again, included in the resort fee I didn’t pay. While there, she told us many boats had cancelled due to large swells being forecasted. When we arrived at Molokini there were only 4 boats there. I am assuming the smaller boats cancelled as they couldn’t make it out of the harbor.
The ride was very choppy, but once at Molokini the it calmed down a bit. The water was insanely clear, and we had beautiful views of the coral and the fish. Even the fish all the way at the bottom were easily spotted.
They usually make a second stop at Turtle Bay, but due to the swells, the visibility there was close to zero. So instead, the captain did a slow drive back, stopping to see the whales. These magnificent creatures were everywhere, but no matter how many we saw, it never got boring.
Getting back to shore, we were completely exhausted and took a nice long nap.
Supper was from Chabad and was also delicious. After dinner we went to check out Shops at Wailea before turning in for the night.
DAY 7-WEDNESDAY We had scheduled a complimentary outrigger excursion through the hotel, but they cancelled due to high swells. Since we enjoyed seeing the whales so much, we booked an official whale watching tour on Pac Whale adventures.
The staff were knowledgeable and walked around answering any question people had. They have a special program for kids as well. It did drive me nuts that they kept talking about their non-profit organization and trying to solicit donations, but am glad I managed to get the whale watching in.
Right after we arrived back to Andaz, I ran up to get our suitcases while DW selected photos from our shoot. The guy manning the desk wasn’t overwhelming, and stepped away while she chose, not pushing her to purchase more than we had planned.
Checked out with a folio of $9 (Best coffee I had on the island), went to Costco to fill up the tank and headed to the airport.
We ordered food from Oahu Kosher for the flight home since Hawaiian doesn’t offer any kosher meal. Pickup was very easy, right near the terminal.
We went to the tiniest airport lounge, which didn’t even have restrooms. It was basically a fancy coke stand.
Flight was comfortable, but Hawaiians first class seats were a lot less comfortable and less spacious than our United flight. All things considered, DW managed to sleep through the entire flight.
Leaving Hawaii 
Welcome to NYC Maui lived up to our expectations and beyond! Hope to be back soon.
