Believe it or not, I am starting this post right after publishing the last one. But, if history repeats itself, this will take me a few months to finish. Let’s see how it goes!
Update: As predicted, this took me several months to finish.
In May 2026, Justin and I had the opportunity to travel to Maui, Hawai’i. Our last visit to Maui was over 8 years ago – in 2018. We were excited to be coming back after several years, and were interested to see how things might have changed – we are also much more experienced travellers now and better at putting together itineraries.
The theme of our trip was that we would have to do everything twice. In some cases this was by choice, whereas other times we were forced due to natural circumstances – keep reading and you will see why!
Day 1
Our first day in Maui was consumed by travel. Our flight left Vancouver close to 7pm, which meant that we landed in Maui at 10pm local time. By the time we got our baggage, rental vehicle, stopped at Safeway for a couple of essential groceries and got to our accommodation, it was past 12am and time for bed!
After some much-needed sleep, we were ready to start our actual first day in Maui. We started our day by walking along Kamaole Beaches 1, 2 and 3, which are located right by our accommodation in Kihei. Instead of walking back the same way we came (along the beach), we opted to walk along South Kihei Road to check out some shops, but also to see the damage that was done to the road by the floods a couple of months prior. The road was completely washed out and it did not appear that any repairs had been started.
After our morning walk, our first day mostly consisted of getting ourselves organized for the week. We made a mandatory trip to Costco, where we stocked up on groceries and snacks, and also browsed the clothing section because well, everyone does this at Costco, right…? Anyway, we try to keep our meals simple while on vacation – for this trip, we made oatmeal for breakfast, sandwiches for lunch, and pasta with vegetables and tofu for dinner. For snacks we got roasted edamame, apples and protein powder. After Costco, we also stopped at Walmart for groceries we did not need to buy in bulk. At this point, we had everything we needed (for now) and it was time to get back to enjoying our vacation.
Our next stop was the South Shore Tiki Lounge for Happy Hour. Of course, leave it up to me to select a drink that was not on the Happy Hour menu, but I had worked up an appetite for a piña colada and was not leaving without one! We ended up staying at South Shore Tiki Lounge longer than expected because Happy Hour also included live music. The music entertainment that evening was being put on by Tiki Tyler, and he did a great job of engaging the crowd. He was taking song requests (including my request for The Bar Song by Shaboozey, which he had to learn on the fly) and even sold kazoos to members of the audience – we all became part of his band, and there were a couple of great soloists!
Day 2
We started our second full day in Maui by driving out to the North-West side of the island. This was around a one-hour drive from our accommodation in Kihei.
We wanted to start our day by getting our steps in at the Kapalua Village Walking Trail Lake Loop. While not the most scenic trail, the Kapalua Village Walking Trail Lake Loop is part of a trail network surrounding an abandoned golf course. At certain points of the trail you are able to see views of the ocean, and you will also walk around a small pond, where we saw several ducks and other birds. We actually even witnessed our first duck fight!
Following this trail, we made a quick stop at the Napili Farmers Marketplace to check out some of the local artisans and live music before heading to A’A Roots for our first açaí bowl of the trip. I had the blueberry muffin special, which literally had a cut-up blueberry muffin on top!
Our next stop was to enjoy some RnR at Kapalua Beach. We enjoyed reading on the beach, along with a bit of swimming, and I am pretty sure I fell asleep and had a nap at some point! My only recommendation for this beach is to show up early, as there is very limited free parking – unless you are fine with paying, then show up any time ツ.
Our last stop of the day was Whaler’s Village in Ka’anapali. Ka’anapali is a resort area along Ka’anapali Beach, with several hotels connected by a beachfront boardwalk. During our 2018 trip to Maui, we stayed at the Westin Nanea Ocean Villas, which was newly opened at the time. The boardwalk starts near the Westin, and passes several resorts before ending at Whaler’s Village, where you can find a variety of shops and restaurants. It was nostalgic returning to Ka’anapali, as we completed this walk nearly every day during our previous visit.
A helpful tip if you drive and park at Whaler’s Village: you do not need to pay for parking if you make a purchase at one of the stores – they can validate your parking for you!
We finished up our second full day in Maui at Da Kine Shave Ice. We got the Lava Flow flavour, which included butter rum, strawberry and banana flavoured syrups. The Lava Flow also comes with ice cream on the bottom – they even had plant-based vanilla! All the syrups are locally made, and they even had syrup options that did not include any colour dyes. It was safe to say this would not be our only time visiting Da Kine during our trip.
Day 3
By my own definition, our first two days in Maui were pretty “chill,” but by the third day, we were ready for an adventure.
We were up early on day three to head to the top-rated hike on the Island – Waihe’e Ridge Trail. The gate to the trailhead opens at 7:00am, and we read that the parking lot is small and fills up quickly. For this reason, we made sure to arrive at the gate by 6:45am, and I can confirm that the parking lot is small. There is overflow parking located by the gate; however, it will add at least an extra kilometre to your hike… each way. One other thing to note is that one of the reviews I read said there was a porta-potty by the trailhead, but take my word for it – there is not. This is your warning to make a stop along the way to use the bathroom, otherwise, you will be forced to find some tall grass or a bush ツ.
Another thing we read in the reviews is that the western mountains in Maui get a lot of overcast weather and rain, and the clouds especially like to “hug” the Waihe’e Ridge Trail. Well, the day we picked to do this hike was no exception. My hair was soaking wet from the humidity of the clouds (I literally looked like I had just stepped out of the shower), and I was incredibly thankful for my hiking boots and poles as I navigated the slippery trail conditions.
Suffice to say, we did not get the beautiful views we hoped for at the top. However, it started to clear up a bit (not completely) on our way down, allowing us to take in some partial views of the Island and coast line.
Following our unsuccessful hiking attempt, we went to check out the Tropical Plantation in Waikapū. We spent around an hour exploring the grounds here – there is a main gift shop at the entrance filled with roasted coffee, chocolates, jams and other food items, but if you keep walking along the path once you exit this store, you will find other smaller gift shops which sell locally made jewelry, pottery and clothing. I personally picked up some glass bead earrings from La Casita Maui made by Kii’nalu Art – a local jewellery maker from the northern part of the Island.
The property also contains a restaurant, along with a pond – we saw several birds and ducks having a sun bath, and even small turtles swimming in the water! You can also take a train/tram tour of the property; however, we skipped this option as the reviews online were not overly positive.
Following our visit to the plantation, we finished up our activities for the day with a swim at Keawakapu Beach and watched the sunset from our accommodation!
I will cover the rest of our trip (and the meaning behind the blog’s title) in my next post – stay tuned!
Always grateful,
Michelle
Exploring With Gratitude 