Hawaii Photo Diary + Travel Guide (11 Days on Maui + Oahu)

Hello hello, so unbelievably excited to get to share our Hawaii trip with you here. I started this post somewhere in the air between Maui and LA, trying to get things out of my brain while they were fresh, but here we are a few weeks later and I’m finishing up.

Some quick background, our friends Dan + Katie (who we visited on our PNW adventure) got married in Hawaii, which was the reason behind our trip. But, if you’re going to spend about 13 hours on planes, we decided to extend our stay to 11 days to make it worthwhile.

(this is going to be a LONG post, with a TON of photos, but each day I bulleted the highlights so you can move quickly through if you prefer)

We opted to fly in and out of Grand Rapids for convenience (not a huge airport), so our flights were: GRR – Chicago (ORD) – San Francisco (SFO) – Kahului (OGG).

And on the way home: Kahului (OGG) – Los Angeles (LAX) – Chicago (ORD) – Grand Rapids (GRR).

If you’re flying out of the Midwest prepare for a solid day of travel on each end, especially because Hawaii is 5 hours ahead of EST.

Day 1: Travel day + Hostel Stay

We left GR at 12:30pm on Friday, January 29th and arrived in Maui that night around 10:30pm (which felt like 3:30am) to us so we promptly went to our hostel and fell asleep. We stayed in a hostel because (I don’t really know) but it was my first time in one and let’s just say it might also have been my last? I’m old now and like the comfort of not a bunk bed haha. Anyway, we booked the Banana Bungalow Hostel mainly for the cost + ease but if I were to do it again I’d book a hotel. 🙂

Day 2: Getting the Green Machine + Road to Hana

Highlights:
-the Green Machine
-Baldwin Beach park
-Baby Beach Paia
-Hookipa Beach
-Twin Falls + rainforest
-Hana cultural farmstand
-Rainbows for DAYS

On Saturday (1/30) we woke up bright and early with the time change and all showered before walking to breakfast. The Tasty Crust is a laid back local breakfast spot that was close to our hostel. We enjoyed our food, and I was introduced to POG juice (combo of passionfruit, orange and guava) and my life will never be the same again. After breakfast we walked back and waited for our ride…aka the Green Machine. The Green Machine is a converted van we rented for the weekend to drive, camp and explore Maui. We rented the Green Machine from a couple who kindly dropped it off to us. We booked it through Outdoorsy – check out the Green Machine in all her glory here.

It sleeps 4 (pretty close quarters), but has a stove to cook, an outdoor shower hookup, and the bed converts to a table in the back which was great for us. Once we got all set up we headed to Whole Foods (for alllll the snacks) and hit the road. Our goal for Saturday was to drive the road to Hana and stay in Hana before exploring the next day (Sunday) and ending up back in Kahului on Sunday night.

The views on the Road to Hana are insanely beautiful. We started our journey later in the day than many do, so we didn’t stop at as many roadside stands as they closed early. But we visited Baldwin Beach Park, Baby Beach, Hookipa Beach, Twin Falls + the Hana Cultural Farmstand. All of which I would highly recommend.

Hawaii is absolute magic my friends. We saw multiple rainbows every single day.

Now, if you follow me on Instagram, you know that we had a few hiccups with this plan. First, we assumed that finding a place to park the van and camp would be easy. WRONG. Especially during Covid. Maui is not a free camp friendly place. So, if you want to rent a camper van and camp in Maui (great idea) you need to reserve a camp spot. Options for this include both state parks and private spots. Wai’anapanapa State Park has camper van spots + camp sites available for rent in advance, and the website hipcamp is an option for booking private sites.

What I would recommend NOT doing is trying to hide your van casually in a park parking lot, then getting asked to leave by the police at 10pm, then driving aimlessly for a bit in a thunderstorm looking for a place to try and hide a vehicle entitled the Green Machine, then wedging yourselves mostly off into the brush of a dirt road and hoping no one hits your van before you wake up. 🙂

Day 3: Wai’anapanapa State Park + Hakealea National Park + Red Sand Beach

Highlights:
-sunrise on Hamoa Beach
-Wai’anapanapa State Park
-Black Sand Beach
-Red Sand Beach
-Pools of Ohe’o at Hakealea National Park
-driving views of Maui
-Maui Sunday Local Market

On Sunday woke up sweaty and gross in our van at 5:30 LOL – but we had successfully made it through the night. I think it was Brendan who said “so no one is falling back asleep right?” haha, we all agreed and decided to start our day by watching the sunrise on Hamoa Beach, which came recommended to us. Absolutely dreamy.

From there we backtracked a few miles and went to Wai’anapanapa State Park and the Black Sand Beach there. We explored in a cave/lava tube, climbed around, did a little bit of hiking, relished in the beauty that is Maui and used the Green Machine to make breakfast in the parking lot. And the bathrooms for a much needed face washing/teeth brushing haha.

After that we headed back to Hana, stopped for much needed coffee at a local stand, My Tita’s Cafe, then hiked to the Red Sand Beach (we found a route online, need to get there by foot).

The Red Sand Beach was secluded AND stunning. There was a cove area blocked off by rocks so there was some calmer water to swim in. For the record, Hana is tiny, we kind of expected a city but that is absolutely not the case 🙂

After Red Sand Beach it was back to the car and on the road to Hakealea National Park, and the pools of Ohe’o (also known as Seven Sacred Pools). We would have loved to do a sunrise or sunset adventure there but it wasn’t in the cards for us with the timing. You need a permit to do so and can register up to 7 days in advance for one HERE if you’re planning a trip.

Unfortunately didn’t do any bigger hikes at the park, if we had more time we would’ve 100%. But we did get to check another National Park off our list. From there we decided to drive the entire loop counter clockwise back to Kahului instead of turning around and doing Hana again. It was a great choice – the island is beautiful, we had amazing views and better road conditions, and made some stops along the way to enjoy the view, explore and cook lunch.

We were scheduled to fly into the Kona airport on the Big Island Monday morning and after the prior night’s fiasco I decided sleeping in the van again then getting on a plane was not an option for me. So, I ended up booking The Maui Seaside Hotel last minute on Hotel Tonight (recently renovated, very cute). Conveniently it’s located across the street from the Maui Sunday Market, so we checked in, took showers and walked over to support local businesses and food trucks. We purchased dinner, fresh lemonade and cookies from a variety of vendors and took it back to the hotel to eat outside. An added bonus!

Day 4: Leave Maui + attempt to head to Kona…

Highlights:
-Eventually arriving in Oahu after a 4 hour stuck in the airport fiasco.

Monday morning we woke up, met the van owners at the airport and boarded the smallest plane I’ve ever been on to the Big Island. We flew Mokulele Airlines and no joke the entire plane + captain and co-captain totaled 10 people. We had a surprisingly smooth journey from Maui to the Big Island with absolutely amazing view including turquoise waters and MORE RAINBOWS. It felt like we experienced rainbows ALL THE TIME while on our trip and I loved it.

We landed in Kona, excited for our nighttime Manta ray swim that night, and then shit hit the fan. (yes it was our fault.) So, even though all the islands are the state of Hawaii, restrictions and rules around Covid seemed to differ between them. In order to fly to Hawaii from Michigan we had take a Covid test with 72 hours of our final flight to the island. (Our final flight was from San Francisco, so you go off that time – no more than 72 hours prior). We also had to make a Hawaii Safe Travels account, download a separate contract tracing app, upload our trips and reservations, and get a QR code scanned and checked to get it. We did NOT realize that we had to have a negative Covid test within 72 hours of every single flight within the islands (again, our fault, but the man I spoke with at the airport said we were definitely not the first to eff this up and wouldn’t be the last).

So we fly into Kona, get off the plane and go to get our new QR codes scanned – and we don’t have fresh enough negative Covid tests. Because of this we cannot go back to Maui (need another Covid test), and we cannot leave the airport on the Big Island without confirming our lodging and that we could quarantine there. For the record, very few hotels in Kona will allow people to quarantine. And it is STRICT. The airport will confirm with your lodging that you are quarantining there and the police will come check up on you. Not to mention, the Big Island doesn’t have huge cities – so we could barely find ourselves a place to test and none had rapid tests available. PLus, if you’re quarantining you can’t leave to get a test.

So, here we are. Literally stranded in the Kona airport, calling any and all hotels and lodging. Nothing. (we also hadn’t eaten breakfast yet so that was fun.) After a few hours of attempts, calling different airports, etc, etc we decided the smartest move was to get marked and “in transit” instead of “quarantining” in the app, fly to Oahu (looser restrictions) and book a Covid test there. Which is exactly what we did. After about 4 hours in the Kona airport we flew into Oahu, rented a car, and booked the Hilton Waikiki (yay for Artur’s work travel points!).

Conveniently Hawaiian Airlines has affordable and frequent flights between the islands and is a solid airline. We flew them from Kona – Oahu, then Oahu back to Maui (after all of this). Very positive experience!

Once we got to Honolulu we all breathed a collective sigh of relief, found some açaí bowls at Tropical Tribe, and walked around Waikiki before heading to the Hilton to shower, get settled and walk to dinner.

Day 5: Honolulu + Pearl Harbor

Highlights:
-Covid testing
–Pearl Harbor National Memorial
-Waikiki Beach

Our first full day in Honolulu was Tuesday, February 2nd. We started off strong by walking to pick up local brunch + coffee from Eggs n Things and Kai Coffee. Then headed to take our Covid tests, where we found this awesome mural (see below).

From there we headed to visit the Pearl Harbor National Memorial. We lucked out because we walked right in, and the ranger at the front told us that normally the line wraps out to the parking lot (a perk of traveling during Covid?!). We didn’t opt to pay for any specific tours, but walked through the museums, read, learned and explored.

Since we couldn’t get rapid tests we made the call that day that we would not be going back to Kona (we had hoped maybe we could catch the tail end of our journey + hit Hawaiʻi Volcanoes National Park) but it truly wasn’t worth adding even more flights and chaos to our adventure.

Not going to lie – we were all pretty stressed about the loss of everything we had booked on the Big Island plus the added costs of more flights, more lodging and more Covid testing. But, over the course of the next few days everything miraculously worked out. First, our Manta Ray tour gave us a full refund, then our AirBnb for the first two nights actually had a property in Honolulu, so they were able to transfer us then cut us a deal for the added night. And, our Turo Jeep rental and tiny house near Volcano National Park both gave us a full refund. This is the tiny house we had booked, and while we never got to visit, the owner was absolutely amazing to us. Hopefully one day we will get to stay there and visit the National Park. While we were all pretty disappointed we missed out on the Manta Rays and the National Park, we truly got so lucky with how kind everyone was with refunds.

Yes we did each pay way too much for another Covid test and yes we had to book a few extra flights but overall it could’ve been SOO SOOO much worse and people are truly good.

After visiting Pearl Harbor we headed back to the hotel, got our beach gear, found some local food then went out to enjoy Waikiki! We also snuck in a lift at the Hilton – they actually had a solid hotel gym. 🙂

Food in Honolulu that we enjoyed over the course of our time there:

Tropical Tribe – Brazilian açaí
Maui Brewing Co.
Eggs N Things
Kai Coffee
Shorefyre
The Sunrise Shack
Poke Bar
Cafe Glace
Island Vintage Shave Ice
and Yardhouse (haha not local but we love it)

Day 6: Honolulu + shopping + relaxing

Highlights:
-a slower day we all needed
-local shopping
-beach walks
-takeout + gelato

Wednesday morning we woke up to rain which allowed us the slow day we all needed after the whirlwind of the previous five. Lexi and I opted to get coffee + bagels and walk to the beach while the guys headed back to Eggs N Things for takeout brunch. We spent the day walking in Waikiki, doing a little shopping, eating more açaí (from The Sunrise Shack this time) and a little napping. Lexi and I each found cute items at Mahina, a local boutique. We got our negative COVID test results back as well (whoop!), which meant we could get back to Maui for Dan + Katie’s wedding.

Day 7: Diamond Head State Monument Hike + Fly back to Maui

Highlights:
-Diamond Head Monument
-Honolulu Views
-Making it back to Maui
-Sunset beach walks + our friends!

Diamond Head State Monument is a massive crater formed more than 300,000 years ago. You can hike to the top for some gorgeous views of Honolulu and the ocean. Currently during Covid they are only open Thursday-Sunday, and we were in Honolulu from Monday afternoon through Thursday morning, so we got up and powered through the hike before flying back to Maui.

The hike itself isn’t all that long, but I would recommend doing it slower than we did and really appreciating each view. We basically ran up and down, stopping here and there to take in the views. You could easily spend hours there if you have the time (I’d definitely recommend it). From there we hopped back in the rental car, dropped it off at the airport and boarded a flight back to Maui.

The flight between islands is quick – so we arrived back in Maui in the afternoon, and took a taxi to the Hyatt Regency (where our friends + the wedding was). We were relieved to make it back to Maui and the Hyatt, which would be our home for the next 4 nights (the longest we stayed anywhere). I literally unpacked my entire suitcase into the dresser haha. We ate a late lunch at Umalu (on the resort) hit the pool, then walked the beach with our friends + saw more whales!! The Hyatt actually has 7 penguins that live at the resort which is a fun little aside.

A Covid note – I don’t know how other resorts are but the Hyatt was very strict with their mask policy. If you were not laying in a pool chair, swimming, eating or drinking, your mask was on. So walking up the bar, mask on, walking across the pool deck, mask on, walking through the hotel, mask on, etc etc. They were enforcing their rules as well. I felt very safe during our stay!

Day 8: Resort + Lahaina Exploring

Highlights:
-relaxing at the hotel pool
-sea turtles + whales
-exploring Lahaina
-shave ice

Friday truly felt like our first “beach vacation day.” Aka the first day of the trip we laid in the sun, swam and enjoyed overpriced poolside cocktails. The Hyatt has an amazing gym for a hotel, so Lexi and I enjoyed a quick 45 lift before grabbing coffee (Honolulu Coffee was in our resort) and heading to the pool. It was glorious, and the beach was right next to it – so we went back and forth and actually swam around in front of our hotel with our own goggles because there were so many sea turtles to see!

A really nice feature of the Hyatt is that they have rental cars available on site and you can book half or full day rentals. Knowing we had our Snorkel and Snuba excursion early the next morning, we rented a car Friday afternoon for 24 hours so we could visit a few local spots and Lahaina that night before needing it in the morning. We hit both The Fish Market and Round Table Pizza (north of Ka’anapali Beach) and would recommend!

In Lahaina we hit some local shops (Kai Aloha was a favorite), enjoyed the sunset, ate amazing shave ice from Ululani, and bought some UPF swim shirts before the next day’s excursion.

Day 9: Snuba Adventures + The Wedding

Highlights:
-SNUBA!!
-seeing + hearing whales
-Dan + Katie’s Wedding

Our alarms went off bright + early on Saturday morning at 5:30 so we could grab our things, and drive the 30 min south to Maalea Harbor, where our Snorkel + Snuba excursion departed from. We booked this a month or so in advance, and actually had it scheduled for Friday so we wouldn’t be tired for the wedding. But, Aqua Adventures called me Thursday morning asking it we could switch to Saturday due to weather and I’m so glad we did. It was actual perfection on Saturday.

Snuba is a mixture of snorkel + scuba, so you are using oxygen and can stay underwater for longer periods of time, but you cannot go at deep as traditional scuba because the oxygen tank is floating in a raft attached to you at the surface. (You can see this in our pictures below). The benefit is you don’t need to be certified to do this, and it’s WAY better than snorkeling. You have the mask on, and a regulator in your mouth, then we had weight belts attached around our waist and a harness that connected us to our oxygen tank at the surface (and fins!).

I will admit, I was SO NERVOUS to snuba. I love being by the water, but don’t love fish or open water – both of which are involved haha. Adella (our instructor) was so wonderful and helpful, which made it a great experience. We did two 30 minute sessions – one at Molokini Crater and one at Turtle Island – as part of our tour (you do pay extra for the snuba). The first session it took me a second to get the hang of only breathing through your mouth with the regulator – hence why I’m plugging my nose in one of the photos below (eye rolling at myself). It was so cool because we could stay underwater the entire time, and Adella was in scuba gear guiding us and pointing out different types of fish. We could hear the whales underwater from miles away which was WILD, swim next to a sea turtle (they’re protected – don’t touch them!) and even got to touch/hold an octopus. In addition, there’s a scuba photographer who has his camera underwater and you can purchase the photos for the group and he literally just transferred them to my iPhone so we had them before getting off the boat. There were a handful of other groups on our tour – but they all only did snorkel so we lucked out getting a ton of photos of just us underwater. We all agreed that our two favorite days of the trip were our day in Hana with the black and red sand beaches and our day getting to snuba and go the wedding! This is the link to the exact adventure we booked. Would HIGHLY recommend.

We met at the harbor at 6:45 and were back to dock by 1:00pm I think. So it’s a half day excursion! Anyway, after we snagged some tacos from the Ono Tacos taco truck on the way back to the Hyatt, dropped off the car and then everyone napped/rested, showered and got ready for the wedding.

Day 10: Pool Day with Friends + the Luau

Highlights:
-Enjoying the pool + resort with friends
-Drums of the Pacific Lu’au
-more Ululani shave ice

Sunday was a very laid back brunch and pool day with our friends, before getting pretty for the Luau that night. The Hyatt hosts The Drums of the Pacific Luau on Sunday nights, and you do not need to stay at the hotel to attend. You can make reservations online. I enjoyed learning more about the legends, stories and history of Maui and Polynesia. Also, fire knife dancing is WILD. We got to spend some quality time with our friends after and it was lovely 🙂

Day 11: Final morning in Maui + flying home

Monday – guys snorkeling in front off hotel again, I had a phone interview, we had bagels and coffee from Honolulu Coffee (in the hotel) and had julio take us back to the airport. He drove us to the resort from the airport Thursday and we took his card so we could call him to take us back Monday. He thanked us for supporting the tourism industry.

And that wraps up our trip. I tried to link everything I could but please feel free to ask questions or leave comments. Thanks for following along!
xo, Maddy