Planning Hawaii
Hawaii is one of the most beautiful places on Earth and there’s so much to see and take in on the 8 major islands in the archipelago in the middle of the Pacific Ocean. As a traveler that loves to maximize her time and see everything possible in a new place, it can be pretty difficult planning an 8 day trip. We were originally planning on just staying and exploring Oahu, but as we were planning, a proposal to check out another island was thrown into the mix and some of the group decided to go for a day trip to Kauai. Ultimately, there’s tons to see on each island and we chose most of the highlights for the itinerary, but I would love to go back and explore more!
Logistics
Flights
We were set on going to Hawaii in February, but prices were more expensive around Family Day (Feb 19), so we thought about going earlier than that and planned for February 3 – 10th. Once we figured out dates, I started looking up airfares and booked near the end of November for $650 CAD flying from Toronto to Chicago then Chicago to Honolulu on United Airlines on Feb 3 and flying back on a red-eye flight to Chicago and then Toronto on Feb 10. There are direct flights to Honolulu from Toronto with Air Canada, but they were more expensive. The cheaper flights all had some American airport stop like Chicago or San Francisco.
Interestingly enough, two days before my flight to Honolulu, there were concerns about a huge snowstorm in Chicago, so my flight itinerary changed to fly into Washington D.C. instead of Chicago before continuing on to Honolulu on Feb 3. It worked out okay in the end since we got there around the same time as when we expected to get to Hawaii from Chicago.
The flight back was also uneventful aside from the fact that we left around 5pm from Honolulu and got to Chicago around 5am (which made for a rather miserable overnight flight) and we were back in Toronto by around 9am.
Accommodations
Now that we had firm dates with the flights, we could book accommodations on Oahu. We planned to stay on Oahu for the 7 days we were going to be in Hawaii and since I was traveling with a group of 10, we needed a place that could accommodate all of us without being way too expensive. We found a place on VRBO for about $500 CAD/night which was pretty reasonable and it was super close to Laniakea Beach, a well-known spot for sea turtles. The place we rented was split into two units: (1) a top floor unit with three bedrooms and two bathrooms and (2) a basement unit with one queen bed and bunk bed and one washroom. The location was also super convenient to do lots of fun things on the North Shore of Oahu since it was a short drive away on Kamehameha highway to the town of Haleiwa with lots of food and Banzai Beach to watch the surfers.
However, it was about 45 minutes away from Honolulu, but it was nice since it didn’t feel as touristy and the views from the house were amazing especially near sunrise and sunset! We also got great access to the beaches and there weren’t any huge crowds whenever we went which was a huge difference from our experience in Honolulu – we got peaceful and serene views of waves crashing on the shore:
Morning views of North Shore beach
Rental Cars/Getting Around
We knew we were going to be renting two cars since we had to transport everyone together and we wanted the flexibility to travel around and not have to rely on public transportation (especially to get to our accommodation on the opposite side of the island from Honolulu).
We had originally planned out 6 days worth of activities and we were seriously debating what to do on the last day – when someone threw in the idea of going to Kauai for a day trip. We looked up flights between Honolulu and Kauai and realized Hawaiian Airlines had multiple daily trips and we could do this extra excursion for pretty cheap and within a day if we caught the first and last flight from Honolulu to Lihue and back! However, we would also have to rent a minivan for the 6 people to get around Kauai – but it would be totally worth it! So we booked the earliest HNL-LIH flight at 6:05am and latest LIH-HNL flight at 8:48pm to get the most out of our trip there. Each flight was about 40 minutes which was super short and we also got served their delicious passion-orange-guava juice.
Day 2: North Shore & Honolulu
We spent our second day in Hawaii exploring the area nearby starting with the Dole Plantation which we passed by on our way to our accommodation from the airport the day before.
The Dole Plantation, located right off of 64-1550 Kamehameha Highway, is open from 9:30am to 4:30pm and is well-known for their pineapple ice cream and it really was super delicious! The plantation is open to tourists to wander around, but for the extra attractions such as the Pineapple Garden, Train tour or Maze, you’ll have to pay extra. We did the Pineapple Garden Maze with some timed activities which was pretty fun!
Next, we went to Honolulu to check out downtown and the touristy Waikiki beach area. We parked west of Waikiki beach and walked the length of the packed beach before going into some of the malls near across from the beach. After eating a late lunch, we stopped by the Nu‘uanu Pali lookout for some pictures of the windward coast of Oahu before then heading back towards Haleiwa to spend some time on the beaches around our accommodation.
Honolulu
Nu‘uanu Pali
The weather changes pretty fast in Hawaii – it can be super sunny in the morning, then cloudy and slightly overcast later in the day or it can even rain/pour. Views here are always gorgeous though (no matter the weather)!
Day 3: Pearl Harbor
We planned the next day to spend most of it at Pearl Harbor and learn about some of the American history here.
There’s four sites here to explore including the:
- USS Arizona tickets (free, but requires booking)
- USS Bowfin submarine is beside the starting point of the USS Arizona memorial tour – open 7:00am to 5:00pm ($)
- USS Missouri Memorial – open 8:00am to 4:00pm ($)
- Pacific Aviation Museum – open 8:00am to 5:00pm ($)
- The USS Missouri and Pacific Aviation Museum are on Ford Island and are accessible by shuttle bus only
We spent a full day exploring all of the museum sites and going inside all of the submarines and aircrafts (that we could access).
After that, we headed back to the North Shore to grab dinner around sunset at the Food Trucks near Pupukea and watch the surfers ride the waves across the highway.
Day 4: Diamond Head Hike
We drove to the other side of the island to go hike the Diamond Head Crater at Diamond Head State Monument park ($1 admission)
There were a lot of hikers since it was such a nice day and the trail got pretty steep with stairs at one point.
The views were so WORTH IT!
It was a gorgeous sunny day, so we could see most of Honolulu from our viewpoint. There were also some bunkers on the top of the hill which provided a great location for stunning panoramic views of the surroundings like the stunning untouched coastline and blue waters on the south side and city view in the northeast.
Afterwards, we went for a yummy brunch at Koko Head Cafe near Honolulu before proceeding east towards Kailua Beach. As you can tell, it did get a little rainy before we got to the beach and the forecast looked like there might be more rain later in the day and the next day. So we decided to tackled the Pillbox hike before the rain started.
We wandered through some residential neighbourhoods before we found the start of the Pillbox hike trail – it was definitely quite hidden and the start was rather intimidating since it was a steep upward trail without many trees or easy footholds to start and since it recently rained, there was a LOT of mud in the initial 10 mins of the trail. Once you got past the start, it was a rather constant uphill as you started hiking up the Kaiwa Ridge to get to the two military bunkers (which have been vacated) and the views were pretty amazing of the Lanikai beach. Near the end, we got rained out since the clouds and rain came on so quickly (as you can see in the picture below – the ominous rain clouds were approaching), so we doubled back without going to the end of the trail. It’s quite stunning and I would highly recommend this trail!
View from the Top of the Bunkers along the Pillbox Hike
Afterwards, we went back to Kailua beach and waited a bit for the rain to stop before spending the rest of the afternoon here playing in the water.
On our way back to our accommodation, we had authentic Hawaiian food like Kalua Pig, Lomi Salmon and poi at Helena’s Hawaiian Food before calling it a day.
Day 5: Makapu’u Point Lighthouse Trail & Windward East Coast
The day started out really nice, so we decided to see the other side of the Island that we hadn’t gone to and drive along the east coast (which was super picturesque with lots of green mountains) to get to Kailua for the Makapu’u Point Lighthouse Trail.
View from the Lighthouse Trail walk
The waters were super clear, blue and gorgeous! The walk was a little tough since we were in direct sunlight the entire length of the trail and the temperatures soared to 30 degrees Celsius in the morning, but it was good exercise to build up an appetite for lunch later!
The lighthouse! Some of the people we passed mentioned that they saw some humpback whales earlier in the day (which made me a little sad we missed them).
We ended our hike with a treat: the BEST LILIKO’I PANCAKES I’VE EVER HAD at Moke’s Bread and Breakfast.
While we were eating, a short heavy rainstorm dropped a lot of rain and caused some streets to become a big waterlogged, but the storm cleared once we finished eating but it was rather gloomy and overcast the rest of the day. However, it made for really nice photos along the windward east coast of Oahu.
On the way back, we drove up the windward side and made some stops along the way to see Chinaman’s Hat Island and Kuoloa Ranch (from the outside only – we didn’t go in). The Koʻolau Range of mountains were amazing! They were super tall and stunning to admire as we drove along the east coast. I could totally see why Jurassic Park was filmed here – there’s something about the rugged terrain that makes it easy for you to imagine dinosaurs roaming about in that wild and untamed scenery.
After the rain, there was a rainbow in the distance! We didn’t really plan this side of the island, so we just stopped whenever we wanted to take pictures or check out the views. We also stopped at Lāʻie Point State Wayside and took some amazing pictures of the islands and watched some people cliff dive.
Day 6: Kauai
Since our flight to Kauai was at 6:05am and we lived on the other side of the island, working backwards – that meant that we had to be up at around 3:30am to get ready, drive to the airport near Honolulu, check in and wait for our 40 minute flight. So we did it on lots of caffeine…and as many juice boxes as they could provide us (I slept through most of it – but told my friends to wake me up for the juice).
Once we got to Kauai, we picked up our rental van and stopped by the nearest Walmart to pick up breakfast, water and snacks for the day. Then we were off to and Koke’e State Park, Waimea Canyon State Park and Nā Pali Coast State Park to see the Nā Pali coast (about an hour away from Lihue airport).
The views from the lookout points were amazing! Some of the popular lookout points are:
- Waimea Canyon Lookout (mile marker 10)
- Pu’u Ka Pele Lookout (mile marker 13)
- Pu’u Hinahina Lookout (between mile markers 13 and 14)
- Cliff & Canyon Trails (between mile markers 14 and 15)
- Kalalau Lookout (mile marker 18) – best to go here first for better chance of good views
- Pu’u O Kila Lookout (mile marker 20)
Even on a cloudy day, the views of “The Grand Canyon of the Pacific” are spectacular! We did a few short walks to take photos and trekked through some muddy areas. Afterwards, we drove to the town of Waimea for lunch and shave ice, then proceeded to the Kauai Coffee Company for free coffee tasting and a plantation tour which was really neat and exactly the perfect pick-me-up after a brutal early morning wake up and long day!
Once we were properly caffeinated, we headed over to Poipu Beach Park, where we saw some lazy and sleepy monk seals sunbaking on the sand in a sectioned off restricted beach area. We enjoyed some time hanging out with the seals and soaking up the sun on the beach before we kept going to our next destination.
We drove 40 minutes from Poipu Beach to Wailua Falls to take pictures and admire the beauty of this slightly out of the way waterfall.
After that, we headed back to the airport to make sure we could grab dinner and catch our flight back to Honolulu at 8:45pm. By the time we got back to our vacation rental, it was around 10:30pm and we were super wiped from the jam-packed day on Kauai. There was still so much I wanted to see on the island, but we got a pretty good preview for one day!
Day 7: Surfing Lessons in Haleiwa & Polynesian Cultural Center
We started the day with a surfing lesson in Haleiwa with Uncle Bryan’s Sunset Suratt Surf Academy and spent the morning learning the basics on land before heading out to ride small waves in the water. I never realized how much paddling on a board was needed (my arms got the most intense workout of the year so far) and when we got really tired, some of the super helpful teachers towed us out to catch the waves! By the end, we all improved a lot and could ride a few waves without wiping out!
After our surfing workout, we went back for a quick rest before heading back out to check out the Polynesian Cultural Center on the east side of the island about 1/2 hour away to learn about Polynesian culture and experience a real Hawaiian luau.
We watched the parade on the water, learned the hip-swing dance at the Island of Tahiti, threw spears at the Island of Tonga, ate half-moon pies and learned to weave headbands at the Island of Samoa, learned to swing rocks and watched a luau with a full buffet before ending the day with the awe-inspiring Ha: Breath of Life show.
Final Day: Haleiwa & Farewell Hawaii!
We spent most of the final day lazing at our vacation rental and enjoying the beaches nearby which were pretty empty of people (a huge contrast from Waikiki and other bigger beaches). Unfortunately, we never saw any sea turtles at Laniakea Beach (even though it was like a 5 minute walk from our accommodation), but we heard they usually come there around sunset (and we were always too busy doing other things to make it back in time to see if the sea turtles came). We also spent some time in Haleiwa before some of the group had to leave early to catch their flights back home. We had lots of shaved ice and food truck eats!
When it came time to head towards Honolulu to catch our flight, we made a quick detour to pick up a slice of Macademia nut cheesecake at The Cheesecake Factory (a MUST-DO whenever I’m in the USA) and I must say, the macademia nut cheesecake tasted even better in Hawaii than when I tried it in the rest of the US (Hawaii produces a lot of delicious macadamia nuts amongst other things).
Tips
- It is essential to rent a car in Hawaii because it makes getting around so much easier! Compared to Canada, things are a much shorter distance apart even if the highways are one-lane only. On Oahu and Kauai, it took 45 minutes – 1 hour to drive from one side of the Island to the other.
- Be prepared for all sorts of weather! It may start out super sunny in the morning, but it could suddenly change and become rainy and overcast the rest of the day and when it rains, it can be a downpour. The weather was mostly pretty hot, but the sea breeze can make it chilly at night.
- Food Trucks are pretty popular on Oahu and the food is pretty good too! Make sure to check them out!
- There are endless things to do in Hawaii! It can be a super adventurous trip with snorkeling and surfing or a calm and relaxing trip lazing by the beach – it’s all up to you what you choose!
ENJOY!
Vacation Travel Log 