Hawaii (Oahu) Travel Tips

Oahu is an incredibly beautiful island – completely conquerable in a car, and with lots of amazing and free/inexpensive (!!) activities. This is by no means a comprehensive list of things to do/tips, but a few things we learned along the way…

Rental vs. Hotel

If you are like us, and prefer the freedom of cooking your own meals, having more space and not being in the hustle and bustle of a city, rent an apartment or house! The hotels were beautiful, and many offer amenities such as pools, numerous restaurants and resort activities so it really is up to you. We rented an apartment on the eastern part of the island and it was the perfect location to get into the city when we needed, but away from the crowds and noise.

We rented through AirBnb and had an absolutely fantastic experience. Here’s where we stayed.


A rental also allowed us to save a ton of money on food. Groceries are definitely more expensive on the island than main land (for a weeks worth it was about $150), but most meals will run you $50 or more per person at a restaurant. We ate breakfast at home almost every day, packed lunches for hikes and even did a few dinners.

Shrimp trucks, Hawaiian food fast food joints and poke bowls are plentiful, delicious and much, much cheaper than most restaurants.  Helena’s for Hawaiian food knocked our socks off, and poke was so readily available, you could essentially get it anywhere. We could usually both eat for around $25 vs. $100.

We tried the famous Alan Wong’s – and it was good – but nothing earth shattering. I would recommend Sushi Sasabune instead – the experience alone was really cool, and if you like sushi, this place is VERY good. This was our one big splurge dinner.


Driving was by no means stressful, and the locals here are incredibly nice about letting you make that left hand turn, cutting into their lane when you realize the exit is a hundred feet away and generally just patient. We rented a car through Thrifty at the Honolulu airport for the week for about $250. Gas wasn’t too astronomical (it was a little under $3 a gallon), and getting around the island is much easier with your own transportation. We drove to the North shore, up along the coast, through the mountains, through eastern Oahu, Waikiki and Pearl Harbor. A GPS is an absolute must because the highways run out and then you are often confronted with having to chose your next move rather quickly. Listen to your GPS and ignore the signs, because many of those are not correct! However, if you do make a wrong turn, Oahu is not massive and you’ll easily be able to get back on track. It happened a few times to us. There are no tolls on the highway too (bonus!).

Which brings me to my next point… parking! We generally found parking wherever we went with the exception of Waikiki. So here are my suggestions for that – if you are going to a museum or a restaurant, ask them about parking. If they don’t offer it, or have limited spaces, ask where the closest garage is. Street parking is liquid gold. It only happened once to us – and you will need quarters! Be prepared to spend a pretty penny on parking lots and garages. Some restaurants, like the Mai Tai Bar, will validate your parking for up to four hours, if you use a specific garage. You’ll get a feel for it and where the best places are to park. We made a lot of reservations on King Street for dinners (coincidentally) and street parking is free and pretty available after 6 pm.

Traffic in Honolulu is insane during rush hour, but pretty easy to navigate at all other times of the day. Just keep in mind when you’re planning activities.

Free/Inexpensive Activities

The hiking! The beaches! They are all free or cheap and in my personal opinion, a thousand times better than time spent at a pool or shopping in Waikiki. We didn’t get to tackle every hike in our book, but here’s what we were able to conquer, with associated entrance or parking fees:

  • Pillbox Hike: Free! Parking is in a residential neighborhood (read up on it before you go). The trail definitely has an incline, and you can spend as much or as little time as you want on the trails. It did rain a bit when we went, and as a warning, the trails can get slippery.
  • Waimea Falls: $16/person entry fee. The falls are located in a botanical garden and this was the most expensive “hike” we did. I would categorize this as more of a walk. The gardens and falls are beautiful, but don’t expect to do this alone. We did the Pillbox and falls on the same day since the latter does not require significant energy.
  • Moana Falls Hike: $5 parking fee. There are a lot of signs that make it seem like there is no parking, but this is a lie. Just go all the way up until you pass a snack shack and there is a parking attendant at the end of the road.
  • ‘Aiea Loop Trail: Free! There are multiple lots to park at for this hike. The hike starts at the last parking lot, but my tip is to park in the first one (near the first bathroom “shed”) and walk up the hill in the beginning. This hike takes about 2 – 3 hours to complete and I can tell you from experience that walking up hill to the parking lot at the end was not fun. 
  • Diamond Head: $5 parking fee (if you walk in, they charge $1/person). Go early in the morning when the crowds are slightly less insane and it isn’t as hot. The hike is not difficult, though there are a few areas with incredibly steep stairs that will definitely get your heart racing! 
  • Makapuʻu Point Lighthouse Trail: Free! The parking lot opens at 7 am, though some people park on the side of the road if they go before the park opens (note there is a lot of broken glass from break-ins, so I’d recommend against that). 
  • Koko Head: Free! This is a HARD hike. I am not going to sugar coat it. It was also probably my favorite hike. Go in the early morning to see the sunrise or end of the day at sunset. This is necessary from just a heat stand point. You will climb old tram tracks straight up this mountain. There is a parking lot, though we walked here from our AirBnb because it was so close by.

All beaches on Hawaii are public – so even if they are part of a resort, or seem to be part of someone’s backyard, you can go on them. There are some signs that try and prohibit you from trespassing, but you aren’t. Because it was slightly overcast most days we were in Hawaii, we didn’t spend too much time at the beach. But here are the few we did go to:

  • Kailua Beach: Parking is free, and there are numerous lots. There are facilities with bathrooms and showers. The sand here is SUPER soft, which James loved, but got into literally everything! The current is a bit stronger here so not great for swimming, but would be fun to boogie board at.
  • Hanauma Bay: $7.50/person + $1 parking fee. Make sure you get here early (before 9 am) to secure a parking spot. You will have to watch a brief video on preserving the bay before you are able to go down. Here you can snorkel or swim. I chose to swim because the water was actually calm enough, and had the benefit of still checking out the beautiful ocean life below. Snorkel equipment can be rented onsite – though our AirBnb provided everything we needed.
  • Fort DeRussy Beach: Free! I checked out this beach before James’ surf lesson. It wasn’t crowded at 9 am, though there is a ton of coral here. I brought a pair of goggles and did some swimming, though I can’t say it was very easy. Great views of Diamond Head, and a lot of little shops on the beach that can provide you with chairs and umbrellas if you’re spending the day.
  • We also walked along beaches in the North Shore – great for watching surfers, not great to swim in (current is VERY strong here), as well a picnicked at Kualoa Point. A sunset was watched from Waikiki beach one evening at the Mai Tai Bar (which goes right up to the sand).

Other affordable activities? Drive up to Waialua (North Shore) and walk around the surf town. Grab a coffee at the Coffee Gallery, and hang out in their outdoor shaded patio area. Alternatively, you can go to Kailua, hit up Morning Brew, and walk around the town.

Visit Pearl Harbor – this is technically free, but I opted to pay $3 to reserve a space on one of the tours to the USS Arizona. Definitely worth it, as these tours tend to be “sold out” every day.

If you have a museum membership, see if they offer reciprocity memberships elsewhere. We were able to get free admission to the Bishop Museum in Honolulu.

The Shangri la tour comes with free admission to the Honolulu Art Museum, and Iolani palace was surprisingly affordable as far as palace admissions go.

Bring Cash! 

If you have to pay for parking or admittance fees, make sure you bring cash, because almost all of these are cash only. We brought $100 in cash with us and spent about half.

And some of my favorite photos… 

Hawaii: Day Seven

On our last day on Oahu we woke up to a beautiful sunny, mild day (OK it was still dark, but it looked promising!). Because the previous day had been so rainy, I convinced James to go on a sunrise hike with me, so that we could check one more off the bucket list. At 6:30, we piled in the car and drove off to the Makapu’u Lookout trail on the Eastern part of the island.

The Makapu-u trail is paved and well kept (when we were there, someone from the state was actually clearing off the mud and debris from the previous days storm). It’s about a mile to the top, and while there is definitely an incline, this is doable for those who are not as active or pushing a stroller (which I saw a lot of tourists unsuccessfully try to do on other trails).

At sunrise, there were only a few other people on the trail, making this incredibly peaceful and quiet. Once high enough up, there are a few binocular stands to look out across the ocean. If you’re lucky, like us, you might even spot some whales! The end of the trail exposes a lighthouse that’s built into the side of the cliff and amazing views of the island.

We made our way back down and swiftly returned to the AirBnb to clean up, pack our last remaining articles of clothes and rinse off the mud and sweat of our hike. Saying goodbye to our faithful little apartment, we headed into Honolulu for coffee and tea.

Earlier in the week, we stumbled across a public market area with lots of shops and food vendors. Arvo, one of the places we had coffee previously was around the corner, so we decided to give this area a go again. I grabbed an espresso tonic from 9Bar HNL and a matcha mochi bar (gluten free and vegan – and delicious!). James grabbed another chai latte from Arvo.

From here we made our way to the Honolulu Art Museum, where our tour of Shangri La would take off from. James and I were definitely the youngest couple on the tour by about 30 years, but it is fantastic!

Shangri La is the home of Doris Duke, a incredibly wealthy woman who traveled the world and became enamored with Islamic art and culture. Her Hawaiian vacation home was built in the style of Islamic art – and took influence from Iran, Egypt, Turkey and many more countries. It was stunning.

A tour guide brings you through her home, pointing on fabulous work that she either bought or had commissioned. In 1939 the house cost $1.4 million, a pretty penny then. The property overlooks Diamond Head and Doris Duke ensured easy access to swimming and surfing. I highly recommend – and if you’re worried about spending indoor time when it’s sunny out, fear not, the tour actually has a decent amount of time in her gardens.

Upon returning to the art museum (which you do receive free admission to if you book the Shangri La tour), we headed out to find our final poke bowl. We ended up at a make it yourself poke bowl shop and then drove around until we found a little park we could stop at and eat.

Our rental car was due back at 2 pm, so we headed to the airport after this. It was a good thing we would be at the airport so early, because that horrendous trip to Hawaii? It was repeated on the way home. The JetBlue attendant who refused to close out the transaction in New York caused a freeze on our tickets and no seats on our return home. We made it on the plane with a matter of minutes to spare. And in case you’re wondering, Honolulu’s airport is partially outdoors, which means that when you change into your winter clothes once you make it through security, you will definitely be sorry as you run through the airport to your gate.

Hawaii: Day Four

Day Four brought us to Kualoa ranch for the Premier Movie Tour. The ranch, which was owned by Hawaiian kings and queens, was eventually purchased by a man named Dr. Gerritt Judd, a Bostonian who fell in love with the islands and renounced his citizen to stay in the 1850s. Since then, it has passed down generation to generation in his family, who have continued to cultivate and protect the land. You can learn more about the history here.

Our purposes at the ranch were a bit different than raising cattle or farming. In the mid-1900s, the ranch started to be used as movie and television sets. For James and I, this was home to Jurassic Park, Jurassic World and LOST (among many more). The nearly three hour tour took us winding through three different districts of the ranch, pointing out areas and some sets that are still in existence. We saw Hurley’s golf course, the log that the kids hid under in Jurassic Park from the T-Rex, the Gyrosphere pavilion from Jurassic World, as well as the cage that held the mutant dinosaur. There were props from movies in post production, barracks from World World II and plenty of wildlife.

Gyrosphere launch pad.
Gyrosphere launch pad.

Ahhhh the scratch marks!
Ahhhh the scratch marks!

We also learned about some Hawiian folklore. Chinaman’s hat, one of the island/rock formations off the coast earned that name recently. But before, it was thought that a goddess’ sister defeated a giant lizard monster and the mountains were his dead body, and the single spike in the water (or the hat) was part of his tail.

The island also still marks their ahupua`a divisions – areas of sacred land – with brown signs that look like they have a pile of poop on them. The drawing on the signs is in fact, a pile of rocks with a pig on top (pua is pig in Hawaiian). Speaking of pigs… we also had the chance to see a little fleet of wild baby piglets run through the woods. They’re technically destructive to the plants on the ranch, but so cute!

After the tour, we headed to Kualoa point to have a picnic on the beach. At this point, we had anticipated it to start raining, but it had yet, so we took the opportunity to hike the ‘Aiea Loop Trail, a nearly 5 mile trail around the ridge of Halawa Valley. The trail itself is protected from the sun by the woods (it reminded me a lot of the hikes we have at home – just different plants). At certain points you can see out to Pearl Harbor, and even the highway that cuts through the mountain. The amount of energy used to hike the trail is not anything near the amount to do Koko Head, but this is not an easy trail. There are extremely narrow parts of the path with a massive drop if you slip, logs you have to duck under and climb over, and a lot of exposed roots and slippery sand and mud. Regardless, we enjoyed the trail and took full advantage of the surprisingly sunny afternoon.

Because the next two days are supposed to be a bit dreary, we decided that it was our final opportunity to see the sunset on Waikiki. So we made our way to the Maitai bar at the Royal Hawaiian hotel. Here we secured seats on the beach, overlooking Diamond Head and the beautiful Pacific ocean. James ordered a shirley temple in a pineapple (because when else is it going to be accepted to do this?!) and I tried their maitai recipe from the 1940s. I don’t know how people can drink multiple maitais, because that just about did me in! The sunset was absolutely stunning, complete with a rainbow, and the rain started to fall just as we paid our check.

James making the Brody face.
James making the Brody face.

For dinner we had Bubbie’s ice cream because vacation. I had macadamia nut and chocolate almond. James had macadamia nut and strawberry cheesecake.

Hawaii: Day Three

James’ surf teacher recommended doing the Koko Head hike at sunrise. He said something along the lines of “you need a light at the end of the tunnel” which I shrugged off (spoiler alert, I shouldn’t have!). So this morning we woke up early, and headed over to the trail (just a couple of blocks from our AirBnb).

Koko Head might be one of the most difficult hikes I’ve ever been on. While the elevation isn’t as high as some other hikes I’ve done, the 1,200 feet in the air – or the 1,048 steps really is something. The trail follows an abandoned tram railway. But what was really terrifying was the section of railway that was essentially a bridge with no ground underneath, going up the side of this crater/mountain/hill. I hugged the tracks and rails as if my life depended on it (and it probably did!). But I made it successfully up and down, without a scratch or bruise… just plenty of mud and sweat!

It's a long way up!
It’s a long way up!

The views on the top of Koko Head absolutely make up for the difficult hike – and I would advise that if you ever attempt this, to go very early in the morning or later in the evening when the sun is not that strong.

Terrifying bridge
Terrifying bridge
When you hit the summit, you are able to see a few of the other islands of Hawaii.
When you hit the summit, you are able to see a few of the other islands of Hawaii.

Legs shaking like crazy at the bottom, we made our way back to the AirBnb and immediately changed into our swim suits to spend some time at Hanauma Bay. The bay is famous for its snorkeling and we made it in with just a few parking spots to spare. After watching a brief intro video, we headed down to the bay.

The water was so cold. The first 45 minutes or so I would dip my feet in, chicken out and return to my towel to read. Finally we decided to just go for it, and dove in. While most people snorkel here, I took the opportunity to just use my swim goggles and get in some swimming while the current wasn’t too horrible (James snorkeled). The bay is filled with coral reefs and amazing colorful fish (and maybe an octopus). I easily spent an hour swimming and diving down, enjoying every moment of it.

Once we dried off, we headed back to the apartment for a quick lunch of homemade poke bowls, before driving to the Byodo-In Temple. The temple was built in the 1960s to commemorate the 100th anniversary of the Japanese arriving in Hawaii. It’s a replica of a temple in Japan that’s nearly 1,000 years old – and it is absolutely stunning.

Desperately needing a caffeine fix, we head to Morning Brew in Kailua, which we originally intended to hit up on our first day here (but was side tracked due to the day before interrupting our plans). This coffee shop did not disappoint! James had a chai shake and I ordered an iced latte. We strolled around this little beach town, stopping in shops and enjoying the afternoon sun.

On our way home, we stopped at the Blowhole, a hole in the lava by the coast. When the tide is high, water shoots up from the hole, imitating as you guessed it, a blowhole on a whale.

We finally made our way back to the apartment, and spent the remainder of the afternoon reading outside on the deck, and waiting for the sunset (which a cloud blocked at the very last minute!).


Hawaii: Day Two

In true fashion, I woke up super early because time zones and jet lag and I just generally am an early riser. Luckily I had made cold brew coffee to tide me over until breakfast. We made reservations at Hau Tree Lana, which is famous for their breakfast. The restaurant is literally on the waters edge, dripping in pink table cloths and filled entirely with Japanese tourists. I ordered the seafood omelette and James had the Hawaiian breakfast platter which consisted of poi pancakes, sausages, eggs and half of a pineapple. Breakfast was good, but we both agreed that the day before was better.

Following, we headed down to Waikiki for James’ surf lesson. Since we were early, I decided to go for a swim. I wouldn’t say that swimming on Oahu is easy. The currents were definitely more manageable, and the water was not nearly as cold as Kailua Beach, but the coral. The coral is everywhere. Sharp and scary. I swam for 20-25 minutes, but would often have to stop because suddenly I was on top of coral, despite being way over my head. It was definitely an experience!

We headed over to Ty Gurney’s surf school, where I had booked James a two hour private lesson. After signing a waiver and getting fitted for a rash guard, we headed down to a small “private” beach area. I planted my butt down in a chair that the surf shop loaned me and spent the next two hours enjoying the sun and reading. James officially loves surfing, reported he was able to stand up a few times on waves (I can’t confirm as he was literally a speck on the ocean from my viewpoint) and left ravenously hungry.

These are the best coffee cups.
These are the best coffee cups.

We had packed a picnic, but since we are in the land of poke, and it is a new found obsession (thanks to the sushi burrito place that just opened in Somerville!), we decided to try it where it’s common fare. We looked up the closest place with the best poke, and set off on a 1.5 mile trek. We did take a slight detour to Olive & Oliver, a delicious coffee bar inside a hotel slash swim club (if I was here on a girls trip, this would definitely be a pit stop, but I am nice and spared James of a day at a secluded pool with a coffee bar).

After walking through the parts of town tourists definitely don’t go through, we arrived at Fresh Ahi Off the Boat, which was settled next to a strip club and across from a McDonalds. The poke bowls were amazing, and worth every painful step in my flip flops. I had the spicy ahi bowl on black forbidden rice. James had the ahi poke bowl on sushi rice. Both were served with miso soup.

There are roosters EVERYWHERE
There are roosters EVERYWHERE

Lunch was followed by a hike to Manoa falls – about 15 minutes outside of Waikiki. There is a small parking fee (so don’t be turned away by the no parking signs! There is a lot at the end!). We changed into our hiking boots and took off into the rain forest. The trail is muddy, slippery and super cool. We walked through bamboo groves and up steep terrain, to be greeted by a very cool and steep waterfall. Our descent down might have been even more difficult than up, given how slippery it was, but we made it, and raced home for desperately needed showers.

James was definitely tired after his surf lesson, but he made it.
James was definitely tired after his surf lesson!

For dinner I made reservations at Alan Wong’s – which is one of the famous, must try restaurants in Honolulu. I emailed ahead about gluten free, and they were quite accommodating (though when the waiter asked me how the gluten free bread was, and I replied “it’s definitely gluten free” he was a bit crestfallen – apparently this is the best gluten free bread on Oahu. Pretty sure it was Udi’s!). I ordered the goat cheese salad and the red snapper. The red snapper was made specially for me since it’s not usually gluten free (usually covered in panko!) but oh my god, the sauce that they serve it with was amazing. Definitely my favorite part. It was a miso ginger sauce, and I must learn how to make this at home because it’s going on everything. James had poke tuna tacos and short ribs. His favorite part of the meal? Dessert. Instead of shaved ice, they freeze a pineapple and shave that instead. It’s served on top of a vanilla panna cotta and also boasts a lot of ginger.

I was surprised by the total cost of the meal – two courses each, plus one drink and one dessert came out to be around $70 each. I had expected a far higher bill – so something to keep in mind if you go!

Hawaii: Day 1

Yesterday was awful. Pure horrible. We had initially booked a direct flight to Honolulu from JFK in New York. Fog in the morning created a delay, and during the flight the “if there is a doctor on board please stand up” announcement came on, which meant we were not making our connection (by literally 15 minutes!). We had to rebook, which should have been fine, but we had the worst experience with JetBlue. I won’t go into too many details, but let’s just say I had to run in many airports to make connecting flights, had a full on meltdown in LAX which resulted in me sobbing at the check-in counter and James left his wallet on one of the planes (which we luckily got back, with literally minutes to spare before our next flight). We got to our AirBnb in Honolulu around 10:45 pm local time (aka almost 3 am at home). That being said, we were determined to make today stellar to make up for it.

The AirBnb we booked is in East Honolulu and is absolutely fantastic. It’s massive to start, with an extremely comfortable bed and amazing balcony that overlooks the ocean and Diamond Head.

Because we arrived so late last night (our original intent was to get in around 4:30 pm), we opted not to set any alarms for our sunrise hike. This ended up being completely fine, as the sunrise from the balcony was just as amazing, and required significantly less energy at 6 am.

Late arrival also meant that we were able to grocery shop. So around 7:30 we drove to Moena cafe at the recommendation of our AirBnb host. The food here was fantastic. I had a vegetarian omlet which was packed with spinach, tomato, pepper and cheese, topped with avocado. James had a plate with grilled fish, eggs and rice. From there, we headed to the grocery store and discovered how expensive life on Hawaii is. A loaf of bread is around $5, baby carrots are $6 and a bottle of wine at home that is usually $10 was $21. We suffered through, knowing that groceries would be cheaper than eating out for every meal (breakfast alone was almost $50!).

Having sacrificed our sunrise hike, we decided to hit up the trail anyway. We hiked the PillBox trail, which boasts as you might have guessed, pill boxes. This was a great hike with lots of steep hills, but amazing views that made up for it.

Afterwards, we decided to enjoy a picnic lunch at Kailua Beach, just down the road. I attempted to go for a quick swim, but the current was just a tad too strong. Though comical to swim in one spot, like nature’s water treadmill. I drudged out of the water and as soon as I did, it started to downpour. We ran for cover, quickly changed, and then headed up to the North Shore.

Our intention was to hit up Waimea falls (if you’re a LOST fan, this is where Kate and Sawyer swim and fight over the case). On our way we kept seeing signs for Haleiwa so we decided to stop off. This is the epitome of a surf town and it was amazing. After finding parking, we strolled around, bought a few t-shirts and eventually made our way to Coffee Gallery, one of the coffee shops on my “must visit” list. It did not disappoint. I had a rosemary mocha latte and James had an iced chai tea latte. Caffeinated, we hit the road and made our way to Waimea falls.

The falls are located in a botanical garden (which also comes with a cover fee of $16 a person – ouch!). After almost being malled by peacocks, we headed up the nearly one mile path to the falls, taking in the garden and enjoying the sun (the rain luckily stopped!). We opted not to swim in the falls due to enough warnings about a bacteria that can cause your brain to swell and you to subsequently die, but if you want, you can most definitely hop into the fresh water pool and swim up to the water fall.

On our way home, we decided to drive down the North Shore, and stopped at one of the beaches to watch the surfers and enjoy a little stroll on the beach. The waves are massive – and at one point, even though I was walking far away from where they met shore, one was strong enough to woosh up anyway until I was standing thigh deep in the water!

Afterwards, we decided to head back home for a much needed shower and dinner. Sunset from our balcony was amazing, and I made a wonderful risotto with balsamic fish to round out the evening.

 Take that crappy travel day!