“Aloha,” our pilot’s welcoming words boomed through the system of our flight to Hawaii. This arguably most-cliched greeting still successfully launched me in vacation mode. I happily settled in my seat with my coffee and croissant (trip essentials), anticipating the adventures ahead. It was time to buckle up; the exciting journey was beginning.

Situated west of the mainland US, the Hawaiian islands are a tropical paradise⁠—a dream destination for every travel buff. Escaping the day-to-day mundane routine to immerse oneself in the laid back lifestyle of the locals for a few days is an attraction in itself. But the main reason that tourists throng Hawaii is the diverse landscape⁠—volcanic mountains, pristine beaches, lush green patches, and luxurious resorts—there’s something for everyone.

Hawaii has 5 islands: the Big island, Maui, Kauai, O’ahu, Molokai, and Lanai. I had heard great things about all the islands, but Maui topped my list. It is known to be just commercial enough to offer fun activities for tourists but at the same time has serene natural vistas.

We spent 5 days in Maui, and I will cover it day-wise in this post. We like to mix things up by planning out important parts of the trip beforehand but also keeping gaps to accommodate any last minute additions.

Day 1: Living it up with plantations and a Luau show

We did not want to load up day 1 with too many activities just to allow ourselves time to adjust to the new place, especially as we had woken up really early for the flight. This trick also possibly accounts for any travel delays, so that you won’t miss out important stuff.

Brunch at the Mill House

As soon as we got our rental car at the airport, we set out exploring Maui. Our first stop was a restaurant situated amidst a 60-acre plantation plot — The Mill House. We had zeroed in on this one as it was on the way from airport to our hotel, and we had read good reviews about the food here. The place did not disappoint! The location of this restaurant is unique, allowing views of plantations and mountains stretching beyond those right from the table. The food was flavorful and made from local ingredients- a must-go place for farm-to-table food lovers.

Pro-Tip: It is also possible to book a tour of the plantations (entails a tram ride through the vast property). We did not do this activity so I cannot offer reviews of the same at this time.

Old Lahaina Luau show

Once we reached our hotel and checked into our room, we had a few hours to rest before our evening show. We had booked an Old Lahaina luau show in advance- supposed to be one of the best on the island. We soon found out that the who experience lived up to that reputation.

Once we arrived at the location (a convenient shuttle-ride from Westin made it quite easy for us), we were greeted by servers, handed complimentary Mai-Tai cocktails and shown our assigned seats. We then had about 45 min to explore the setting. The set up was majestic; adjacent to beach, seating was set up surrounding a center stage. Along the beach trail, small spaces were created for learning about the Hawaiian culture. There was learn a luau short session, coconut shaving demo, and live creation of handicrafts for sale. Perhaps the most unique one was the demo of a sand oven that is traditionally used to make a popular dish on the island- kahlua pua (pork). Demo of the sand oven can be seen in the photo below.

Day 2: Road to Hana, Pipiwai trail

The road to Hana drive is a must-do item recommended on Maui. First thing to know about this drive: it is about the journey, not the destination. There are multiple possible stops along the way, which makes this 50 mile route a multi-hour activity.

Knowing that this would be an all-day activity, we had researched the stops the day before to categorize them. We had the can’t-miss, would-be-nice, and the okay-to-miss ones. Of course, last minute whims or condition do (and did) shake up some stuff, but overall that gave us a decent idea of how to structure our time. This was crucial especially because one of our must-do’s was the Pipiwai trail about 40 min ahead of Hana. More on this specific trail later.

Here are the stops that we ended up taking in the end. These ended up being a combo of online recommendations, Gypsy audio guide recommendations, and last-minute decisions. Also, everyone says this about this road, and it is true, that you cannot see everything. So just prioritize and enjoy the journey instead of making it hectic to check all items off the list.

1) Paia village (marker 0)

2) Twin falls (mile marker 2)

3) Huelo lookout

4) Smoke shop (10.2)

5) Kenae arboretum (16.2)

6) Kenae peninsula (16.8)

7) Ching’s pond (16.8) (Skippable)

8) Wainapana state park/ black sand beach (32)

9) Naimoku roadside market (We missed this one; stop if you are hungry)

10) Pipiwai trail (and 7 sacred pools)

Day 3: Relaxing with a trip to Old Lahaina town, beach, and Spa

After a hectic day 2, we had already left day 3 wide open to recover. The only agenda was relaxing.

We spent the morning chilling at the hotel poolside and a beach walk. The town of Old Lahaina is supposed to be a fun walk, so we headed there in the afternoon. Lunch at Oceanside facing restaurant called Kimos, and after walking up and down the shops along Front street, it was time for massage. We had found a reasonable deal for a couples massage (reasonable here is a relative term; assume that everything is expensive in Hawaii). The massage was great, and we headed back to the hotel super relaxed.

We had about half an hour until sunset, so it was a good time to get into the water. Because any time after 8 am in day was HOT on the beach! We enjoyed the sunset at the beach and freshened up before heading out. We went to Monkeypod for dinner, a restaurant that was just a 5 min walk from our hotel. The food there was great (their Mai-Tai was definitely the best one I had on the island).

Tip: The fresh catch of the day section was really expensive! It may taste great but just a heads up. There will be other options on the menu though that are more decently priced.

Day 4: Picnic, Helicopter tour, & dinner cruise

Thanks to all the relaxing on day 3, we got an early start on day 4. I am a picnic lover, so the moment I had seen sha dedpicnic tables near the beach close by, I wanted to go there. We picked up banana cream pie from Leoda’s kitchen and pie shop (another of our must-go places during planning). Lucikly, there was a fruit stand right beside Leoda’s, so we picked up some mangoes for our picnic. It’s quite a weird assortment but I loved it! The spot was serene and there is something about sea-breeze that just makes me happy.

We had planned a Helicopter tour in the afternoon and a dinner cruise in the evening. Turns out that waking up early leaves a lot of spare time. We had a few hours to kill before the afternoon plans, so we went in for an impromptu escape room right next to our hotel. We have done escape rooms before (and always enjoyed them) but they were generally in larger groups. This one turned out to be amazing even though it was just the two of us. We attempted the medium level bunker themed one and finished in about 42 min or so.

We even found an hour for a free Eukalele lesson at our hotel!

Before heading out to the Helicopter ride, we decided to take on the challenge of squeezing in one more of our wish-list restaurants for lunch. Da kitchen is a small place neat the helipad, but we luckily got seats just in time to gobble up some food. This restaurant is famous for meat dishes, so if you prefer vegetarian, you can skip this one for sure.

Helicopter ride over West Maui and Molokai islands

I am pretty comfortable with airborne activities, so I was quite excited about the Helicopter ride. It was a unique experience – to say the least! Just the way helicopter works – rising up in the air without traditional running take off of an airplane that we are used to- makes it very special. Secondly, the views were absolutely breathtaking! We clearly saw the coastline with the lava rocks on the edge, but the real highlight was the valleys. Once we entered the valley of Molokai island, the view was surreal. We had a birds eye view of the ush green mountains with multiple waterfalls flowing through them. The feeling of seeing a waterfall at it’s source from above is undescribable.

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Pro-Tip: I do not get motion sick easily, but I still felt queasy during and after the ride. If you are prone to motion sickness, pop a pill before hopping on.

Dinner and sunset cruise with the Pacific Whale foundation

Our next activity was the dinner cruise. I was a little concerned about definitely getting sick on the rocky boat, especially an hour after the choppy helicopter ride, but it was okay. Overall, the cruise was good- sunset views, drinks, good weather. I would admit though that the food was quite below my expectations. The general experience was good, not excellent. I would recommend a cruise without dinner to just see the sunset or maybe an after dinner one if available.

Day 5: Savor the beach and pack up

All good things must come to an end, and so it goes with vacation as well. We enjoyed the beach views in the morning and went back to the Mill house for a before flight lunch. I picked up a sovenier- hand made tiki as well with a story behind it.

Ones that got away: Haleakala sunrise and snorkeling

Haleakala sunrise requires special permit. It was booked out by the time we planned our trip (a month or so before). We also didn’t get any last minute permits so we missed going there (although I am wondering where it would have fit in our schedule). Also, the first most recommended activity in Hawaii is snorkeling. I am not a swimmer, so I wasn’t too comfortable going into the ocean looking for turtles but I will admit that I was on the edge until the very last minute. So although I skipped this activity on purpose, a part of me does feel like I “missed it”.

Would definitely love to return someday. There’s always so much to do and yet feels like so much more is left. Until then, I will settle for memories of the sea-breeze and the literal sand in my hair!