• Tamara Merri

My 2021 Hawaii Adventure

Updated: Jan 10

In April 2021 I went to Hawaii with two new friends for 9 days and we packed in a bunch of adventures to really make it count! We flew into Maui to start before then heading to the Big Island of Hawaii and then finishing at gorgeous Oahu. Below you can expect to find our itinerary and my experience of all our excursions along with photos (some professional, some not) and links to everything... including youtube videos I made of some adventures!

Table of Contents


Day 1 itinerary

  • ʻĪao State Monument

  • Haleakalā National Park at sunset

Day 2 itinerary

  • Haleakalā Bike Tour

Day 3 itinerary

  • Waihee Ridge Trail

  • Road to Hana

Day 4 itinerary

  • sunrise swim

Big Island

Day 4 itinerary, continued

  • Volcanoes National Park at night

Day 5 itinerary

  • Night Swimming with Manta Rays

Day 6 itinerary

  • Volcanoes National Park day hikes

  • Punalu'u Black Sand Beach

  • Mauna Kea


Day 7 itinerary

  • Maunawili Falls Trail

Day 8 itinerary

Day 9 itinerary

  • Koko Head Railway


I'm the one taking the photo with Olivia (middle) and Victoria (right)


We stayed in two airbnbs: here's a link to the first (north side of island, closer to road to Hana)

here's a link to the second (I'm not actually sure why we decided to move).

Day 1 Itinerary:

We're in Maui!!!! We couldn't check in to our airbnb til a little later so after grabbing our rental car we went to go hiked ʻĪao State Monument. It was the perfect introduction to Maui because it gives a little history to the island while also providing gorgeous views. Apparently the trail we did is now closed... here is the all trails link. You get to the "end" and go past the railing to continue on well marked trail for about another mile. When we did the hike there were lots of other hikers and even a boy playing guitar to serenade our halfway point. I do not recommend ever going off trail as leave no trace is incredibly important.

ʻĪao State Monument hike
Technically the end of the hike. Very short, but still a beautiful view

Iao Needle protruding from a lush Hawaiin landscape with a creek flowing below
Iao Needle

the summit/end of the ʻĪao State Monument hike
The actual end of the hike we did (that is technically closed)

After getting settled, we made our way to Haleakalā National Park to watch the sun set. I was COMPLETELY in awe. The drive up to the top of the volcano was a little scary (I was the driver) as there are some areas with no guardrails and a steep drop if you swerve... but going up and up and up ABOVE THE CLOUDS to reach 10,000 feet where the parking lot is had me speechless! I've never seen a cloud inversion before. Once we reached the summit it was just a short walk to the overlook to view the crater edge. While we didn't hike down into the crater, if I ever go back that's definitely on the list- it's called the Sliding Sands Trail and is an 11 mile hike. Apparently it's more popular to watch the sunrise from the cater but I say ditch the clouds (and the additional fee) and go at sunset! It was magical.

standing above the clouds along the summit road to Haleakala
So surreal!! We pulled off on the side of the summit road to take in the view

trial sign at haleakala

view from the Haleakala Crater's edge
Looking into the crater before the last rays of light dipped below the horizon

Sunset from the summit of Haleakala

Day 2 Itinerary:

The next morning I woke up for sunrise and drive to the beach solo to soak in our second day on the island. It's nothing extraordinary to share, but I love the photos!

birds flying overhead against a pink sky at sunrise

birds flying overhead against a pink sky at sunrise

Ho'okipa Beach

The main thing on our agenda for day two was the Haleakala bike tour!!! There are a few companies that offer the experience, but we went with bike Maui. You start in town at their shop and then they shuttle you along with all the gear you need (bike, helmet), to Haleakala. We actually start outside of the official park line so didn't go all the way up to the 10,000 feet mark, but I think there is one tour that does offer that. The bus ride to the volcano itself was totally worth it because he gave us such a thorough history of the island along the way!

So we got dropped off and then the ride down was a self guided tour so you could go at your own pace. We just had to make sure we remembered the route back!! I've inserted some photos below as well as a youtube video of [some of] the ride. It was a truly gorgeous way to see more of the island.

Our tour bus driver took so many fun photos of each guest!

sexy helmets lol

view of Maui from the road

bicycling downhill from Haleakala past jacaranda trees
So many gorgeous jacaranda trees along the route that smelled SO. GOOD.

After the bike tour we relaxed, went then watched the sun set at Waipuilani Park before ending the night at Maui Brewing Co.

Maui Brewery
Maui Brewery

Day 3 Itinerary:

Day three was a big day. We started the morning off hiking the Waihee Ridge Trail before trying to tackle the road to Hana. In hindsight I definitely would have dedicated the whole day to exploring the road to Hana.

That's not to say the Waihee Trail wasn't worth it though because IT WAS!! It was absolutely stunning and we all thoroughly enjoyed it. However it got to a point where we hiked into the clouds and the weather didn't clear up so we never had a view from the very top. But the halfway point was awesome. Since it was kinda crappy weather it was extremely muddy and I slipped and fell a few times ruining my white shorts haha. I definitely recommend this hike! If you plan do go definitely get there early as we got one of the last spots in the tiny parking lot.

waihee ridge trail view

waihee ridge trail view

waihee ridge trail trees
interesting trees along the waihee ridge trail

The Road to Hana is 60+ miles of beaches, waterfalls, and views that is extremely winding with one-lane hairpin turns. Definitely a white knuckle drive! Both Olivia and Victoria felt car sick at some points so at least I was driving. We looked up a few spots we wanted to stop ahead of time and then we also downloaded the Shaka Guide app from the Apple store that proved to be super beneficial! Definitely recommend getting the app if you go because it is a GPS based app that tells you what's coming up along your route and also explains some history of the island. Plus, there's no cell service along the route so it's nice to listen to something!

There are a few spots that you need advanced reservations for, like the main attraction black sand beach Waiʻānapanapa. So make sure to plan ahead of time!