Hawaii - Maui
March 2020
7 Days
We had done a good amount of traveling throughout Europe in 2018 and 2019 as I was spending a lot of time there for work, so we decided that in 2020 we would do a beach vacation for a change. Neither of us had been to Hawaii before, so we chose to just do Maui this trip. With direct flights from Chicago, this would also limit the amount of traveling we needed to do.
There a number of hotels you can book with points in Maui, but the Andaz Maui is notoriously one of the most difficult hotels in the world to book with points due to limited availability and a usual 7-night minimum stay requirement. In the weeks leading up to the trip, I was able to find a 2-night window that had availability and after staying there I can see why the hotel is so difficult to book as it's an incredible property with even more incredible value booked with points.
Contents
Daily Itinerary
Check-In
Sunset on the beach
Morning walk on the beach
Afternoon Mai Tais at Monkeypod Kitchen
Nap by the pool
Dinner at Ka'ana Kitchen
Early morning paddleboard with whales and a mantaray
Breakfast buffet at Ka'ana Kitchen
More beach time before switching hotels
Get settled at Grand Wailea
Dinner at Lineage
Road to Hana
Stop 1 - Garden of Eden
Stop 2 - Halfway to Hana
Stop 3 - Pua'a State Wayside Park
Stop 4 - Nahiku Marketplace
Stop 5 - Black sand beach at Wai'anapanapa State Park
Stop 6 - Wailua Falls
Stop 7 - Hasegawa General Store
Stop 8 - Kaihalulu Beach (Red sand beach)
Poke #1 at Tobi's Shave Ice in Paia
Poke #2 at Oki's
Day 5
Buffet breakfast at Grand Wailea
Sea turtles and sea lions at Ho'okipa Beach
Late lunch at Mama's Fish House
Sunset at Haleakala Summit
Lunch at South Maui Fish Company
Whale watching in Lahaina
Browse the shops in Lahaina
Old Lahaina Luau
Morning surfing lesson
Loco Moco breakfast at Kihei Caffe
Kapalua Tidepools
Nuka
Flights
United Airlines Economy ORD-OGG: 45,000 United miles roundtrip + $11 taxes & fees
Hotels
Andaz Maui: 60,000 Hyatt points for 2 nights
▸ An amazing and newer hotel in Wailea with more of a laid back attitutude and adult focus. Perfect for couples if you can manage to get a reservation.
Grand Wailea, A Waldorf Astoria Resort: 380,000 Hilton points for 5 nights (5th night free perk)
▸ The largest hotel on Maui and great for families with young children. Definitely a bit outdated and service is not as attentive due to the large number of guests.
Food (With Beli Ranking)
Mama's Fish House (9.9) - An absolute must-visit that's been open since 1973, where you have to book reservations months in advance. Incredible food and great atmosphere right on the beach overlooking the water.
Nuka (9.6) - Small Izakaya-style restaurant in the sall town of Haiku. Delicious sushi and other bites.
Morimoto (9.2) - The food is good and the location is incredible, right on the pool in the Andaz Maui hotel with the beach and ocean beyond. A bit pricey as you're paying for the location and the name.
Lineage (8.9) - Farm to table restaurant in the mall in Wailea perfect for groups. Great food with some unique takes on Hawaiian and Japanese cuisine.
Tobi's Poke & Shave Ice (8.9) - Small shop in the funky town of Paia serving what might be the best poke on the island.
South Maui Fish Company (8.6) - Food cart in Kihei serving fresh fish and poke at reasonable prices.
Ka'ana Kitchen (8.6) - Main restaurant at the Andaz Maui hotel overlooking the ocean and serving locally sourced dishes.
Kihei Caffe (7.8) - Always noted as one of the breakfast spots on the island.
Monkeypod Kitchen - Casual spot with good food and the best Mai Tais on the island.
Full Itinerary
Day 1
Arriving at the Andaz was quite literally arriving in paradise considering March in Chicago is cold, windy, and gray. The check-in lobby overlooks the tiered infinity pools leading down to the main pool and the ocean beyond. While we were being checked in, we were given lavender lemonade to sip on and we were given a brief tour of the property on our way to our room.
Andaz Maui - Maui, Hawaii 2020
The Andaz Maui faces west, making it an excellent spot to see the sun set.
Sunset at Andaz Maui - Maui, Hawaii 2020
Day 2
Sunrise Walk on the Beach
With Maui 4 hours behind Chicago time, it takes a few days to stop waking up before the sunrise, but it's a pretty incredible feeling walking along the beach as the sun rises. We planned our trip so that we would spend the first 2 days at the Andaz Maui and just have some beach time. Then, the remaining 5 days once we moved to the Grand Wailea resort we would venture off the resort.
Mokapu Beach - Maui, Hawaii 2020
There aren't a lot of restaurants within walking distance of the Andaz Maui, but Monkeypod Kitchen was one of them and had been recommended to us by a friend. Definitely the best Mai Tai I've had! The lobster deviled eggs and truffle fries were pretty amazing too.
Mai Tais at Monkeypod Kitchen - Maui, Hawaii 2020
Ka'ana Kitchen
Ka'ana Kitchen is the main restaurant at the Andaz Maui, and also where the breakfast buffet is served. The open air kitchen opens to a balcony with seating overlooking the resort and ocean.
The menu is a bit unique in that it is divided by the local producers the dishes come from, rather than the traditional split of starters and main courses. The food was definitely fresh and very delicious - definitely worth a visit even if you aren't staying at the hotel. The Chef's Table experience is a tasting menu also offered separately as it's located in the kitchen with the Chef.
Sunset from Ka'ana Kitchen - Maui, Hawaii 2020
Day 3
Paddleboarding with Whales
The Andaz Maui included many activities with the resort fee, one of which was guided paddle board tours. We did this at 7:30am and got to see a mantaray swim right below us and a couple of whales breach right in front of us!
Paddleboarding at Andaz Maui - Maui, Hawaii 2020
After 2 nights at the Andaz Maui, we moved right next door to the Waldorf Grand Wailea resort. Compared to the Andaz, the Grand Wailea is clearly much older, much bigger, and much more catered to families. Though we were at first concerned about the number of small children, I will say I still had a blast at the pools, waterslides, and most importantly the swim up bar.
Grand Wailea, A Waldorf Astoria Resort - Maui, Hawaii 2020
Lineage was another restaurant recommended to us by a friend, and it happened to be right next to the Grand Wailea. Lineage is a modern take on traditional Hawaiian and Asian dishes. This dish was a Japanese curry with heads of cauliflower instead of meat. Normally, I stay as far away as possible from vegetarian (and especially vegan) dishes but this was absolutely amazing and I would definitely get it again!
Katsu Curry at Lineage - Maui, Hawaii 2020
Day 4
Road to Hana
After our beach time at the Andaz Maui, we were ready to spend some time exploring the rest of the island. The Grand Wailea has an Enterprise Rental on site, so we were able to get a rental car for the day to drive the Road to Hana.
I read a few pieces of advice beforehand and these are the best:
Start early to beat some of the crowds
Plan ahead of time where you want to stop, otherwise you'll never make it to Hana and back before nightfall
You can leave some of your optional sights to stop at on the way back (unless you are getting a 4x4 and going all the way around)
Write down the mile marker numbers as cell service is mostly non-existent.
Bring cash!
We left the resort at 7:30am and I felt like we were about 30 minutes ahead of the larger crowds. Each site we stopped at we were able to park at, but by the time we were leaving there was no parking left.
Halfway to Hana - Maui, Hawaii 2020
Garden of Eden - Mile Marker #10
Our first stop was the Garden of Eden, a roadside arboretum. There are many unique flowers, plants, and trees with some walking trails among them as well as some lookout points where you can see the ocean. While a nice and peaceful stop, it's not a must see if you are pressed for time.
Garden of Eden - Maui, Hawaii 2020
Halfway to Hana - Mile Marker #17
The Halfway to Hana stand has been operating for over 30 years and is a great spot to stop for any snacks (banana bread & taro chips) before continuing. It’s also a good idea to stock up on remedies for nausea if you’re prone to car sickness. The winding curves are no joke!
Halfway to Hana - Maui, Hawaii 2020
Pua'a Ka'a State Wayside Park - Mile Marker #22
This small park sits on a tight bend in the highway, so you can easily miss the parking pull-off if you’re not looking closely. There's a couple small waterfalls and a small swimming hole if you walk a bit down the trail. It's not a world-famous photo opportunity, but a nice little stop if you need to use the bathrooms or ease some nausea from the car sickness.
Pua'a Ka'a State Wayside Park - Maui, Hawaii 2020
Nahiku Marketplace - Mile Marker #29
Nahiku Marketplace contains several food stalls and a cafe where you can try some local foods and get some caffeine since you've probably been driving for at least a couple hours by now!
We got here a bit before noon and were able to park, but as we were leaving it looked like many people were just passing through as there was not any parking left. We tried our first huli-huli chicken of the trip, and some giant coconut shrimp!
Nahiku Marketplace - Maui, Hawaii 2020
Wai'anapanapa State Park - Mile Marker #32
If you only have time for one stop on your trip to Hana, I would make it the black sand beach at Wai'anapanapa State Park. The clear blue water with the black sand make for a truly unique beach surrounded by lush greenery.
Honokalani Beach at Wai'anapanapa State Park - Maui, Hawaii 2020
Wailua Falls - Mile Marker #45
Just after Wai'anapanapa State Park, you'll finally arrive into the small town of Hana. Our original plan was to continue on to the Seven Sacred Pools but it began to rain pretty hard and the roads after Hana became much bumpier. We stopped at Wailua Falls, but decided to turn back after this.
It's not possible to continue all the way around the south side of the island in a rental car as parts of the road are unpaved which is prohibited by the rental car companies.
Wailua Falls - Maui, Hawaii 2020
Hasegawa General Store
The Hasegawa General Store has been open for over 100 years...and looks like not much work has been done to it since it opened. It's a neat place to check out and if you are staying out here probably the best place to get snacks, liquor, or anything else you might need. Surprisingly the prices were not too expensive for Maui, so we decided to stock up on a couple bottles of wine (much cheaper than drinks at the resort!)
Hasegawa General Store - Maui, Hawaii 2020
Kaihalulu Beach
Had we gone all the way to the Seven Sacred Pools, we definitely would not have had time for Kaihalulu Beach (the red sand beach). It worked out for the best, because the red sand beach was the most beautiful stop we made the whole day!
It's a bit tricky to get to and we had a bit of a hard time figuring out where we could park legally. If you use your GPS to take you here, it tells you to go to Uakea Rd which ends at a resort. It seems you can park on the east side of this road (we saw cars with tickets on the other side). On the east side of the road there is an open field behind the Hana Community Center. Walking through the field and toward the tree line, you'll see a path and a "No Trespassing" sign. I think the sign is meant to mean you shouldn't trespass on the resort, but the path leads away from the resort. So, you just follow the path for 10-15 minutes and you'll see the red sand beach. The climb down to the beach is quite steep, so you definitely want to be careful and wear some decent shoes.
Kaihalulu Beach - Maui, Hawaii 2020
We stopped in the town of Paia on the way back and had wanted to get Poke at Tobi's Shave Ice. Unfortunately, we got there about 30 minutes before closing and they ran out of rice! (On our return in 2024 we returned to try their poke and it was excellent)
Paia seemed like a fun place to hang around in for a bit and grab dinner, but I had my sights set on poke, so we went to the Foodland grocery store. At Oki's Seafood Corner, they had a ton of different poke options as well as sashimi.
Poke at Tobi's Poke & Shave Ice - Maui, Hawaii 2024
Day 5
Ho'okipa Beach
Gwen's top wishes for this trip was to see whales, sea turtles, and sea lions. We'd already seen the whales while paddle boarding, and our Uber driver from the airport had told us Ho'okipa Beach is the best place to be guaranteed to see sea turtles.
He was definitely right, since there was one side of the beach that was closed off just for the sea turtles and there were a couple sea lions too. At first we thought we were just looking at rocks, until we noticed some moving out to sea!
Sea Turtles at Ho'okipa Beach - Maui, Hawaii 2020
If you ask anyone about where to eat on Maui, Mama's Fish House is probably the first place they mention, and for good reason. First, the views are absolutely amazing with wide open walls overlooking the ocean. Second, the menu changes daily depending on the fish they catch, so you know it's fresh.
Mama's Fish House - Maui, Hawaii 2020
The Black Pearl at Mama's Fish House - Maui, Hawaii 2020
Haleakala
The sunrise at the summit of Haleakala is always one of the top things people recommend on Maui, but it also requires you to get up by 3am, which we really didn't want to do so we decided that we would try to go up for sunset.
Unfortunately, the weather was so bad on our way up the mountain, by the time we got to the top, we could not see across the parking lot. We assumed it would not clear up in the next 30 minutes (although we found out from others at our resort that it did), so we started the drive back down. As we descended, the weather got much better and we were able to find a pull-off to stop and take in the sunset.
Sunset from Haleakala - Maui, Hawaii 2020
Day 6
I came across South Maui Fish Company just searching for poke and seafood on Google. When we visited in 2020 it was located in a parking lot behind a gas station. The premise is simple - it's a food truck/cart that serves up the daily catch until they run out. We got there a little before noon and were able to get a seat in the tiny seating area.
The fish was absolutely incredibly and 2021 they were featured on Diners, Drive-ins, and Dives and eventually moved to the Aloha Open Air Market in Kihei.
South Maui Fish Company - Maui, Hawaii 2020
Whale Watching
We booked a whale watching tour from Lahaina and while we got to see a number of whales on the surface, we didn't see any breach like we had while we were paddle boarding a couple days before. We did get some good views of the West Maui Mountains.
West Maui Mountains - Maui, Hawaii 2020
Old Lahaina Luau
After our tour we spent some time walking around Lahaina's vibrant downtown with many shops, galleries, and restaurants.
We couldn't visit Hawaii for the first time and not go to a Luau. I read that the Old Lahaina Luau is one of the most traditional experiences. You have the option of choosing traditional seating on the ground or a regular table, however most of the tables seat 8 people so we got to sit with a lovely family of 6 from Minnesota. The Luau is all you can eat and all you can drink, so we definitely had a great time!
Sadly, in 2023 wildfires destroyed most of the town and displaced many residents. Old Lahaina Lusua was mostly spared and able to re-open in early 2024.
Old Lahaina Luau - Maui, Hawaii 2020
Day 7
Surfing
On our day of departure we hadn’t planned to do much before our 2pm flight. On a whim, we decided to see if we could find a surfing lesson for the morning.
We ended up booking with Maui Wave Riders. Our instructor was fantastic, and we both stood up on multiple waves. If you take a lesson with them, Maui Wave Riders also allows you to take a board back out on your own for the rest of the day. I wouldn’t recommend going to Maui and not surfing!
Surfing - Maui, Hawaii 2020
After a couple hours of surfing, we were quite hungry so we stopped at Kihei Cafe just across the street from the beach we were surfing at. It was our final stop of our trip, and a delicious way to end one of our favorite trips of all time.
Loco Moco at Kihei Caffe - Maui, Hawaii 2020
Additional
Kapalua Tidepools
On our return trip to Maui in 2024 we drove to Kapalua and hiked the Kapalua Trail, a moderate hike which took about 2 hours roundtrip including stops and was mixture of paved and dirt paths. The trail passed along the Kapalua Tidepools which you can walk out to see.
Kapalua Tidepools - Maui, Hawaii 2024
In searching for the best sushi on the island, many resources pointed us toward Nuka in the small town of Haiku. Nuka is a small Izakaya-style restaurant and everything we had was excellent including the sushi, eggplant, and the Nuke bowl.
Nuka - Maui, Hawaii 2024
Overall
Kauai is called the Garden Island for it's lush landscape and definitely a great destination for the outdoor adventurer. There's plenty of great hiking available as well as many great spots for water activities.
When it comes to just sitting on the beach, I'm not sure Kauai is the best (though still very good compared to outside of Hawaii) as we experienced intermitten rain, wind, and clouds each day although the sun would come out again in a few minutes.
Overall, we loved Kauai as it has a good mix of activities whether you want to be very active or just lay on the beach. It's also not as built up as Maui and a bit less crowded.
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