How to plan a trip to Hawaii

Five day Oahu itinerary

Only a year ago I boarded a flight to what many call the Hawaii of China. Fast forward to this year, 2023, and I boarded a flight to the actual Hawaii. I can remember the moment my very close friend told me she wanted me to join her on this trip and I sincerely melted from inside with sheer joy exuding from the grin on my face as I agreed to join her.

Like many others I was ‘stuck’ in China for almost 4 years. And within that time I had not been able to return home, let alone travel internationally. I had plans already in mind to travel home for the summer, nevertheless in the beat of a heart I began to rearrange dates I to accommodate this trip. Long story short I made it to one of my bucket list destinations and I’m more than ready to give you the run down of what I did in Hawaii and tips to make your trip as seamless as possible.

The key to traveling to Hawaii is to know the type of trip you’d like to have. Relaxation, sightseeing, adventure seeking or surfing? What is it you want to accomplish from this trip. The islands have so much to offer and the history is rich. After deciding what your interests are, it’s time to set a budget. Hawaii is one of the most expensive states in The United States, keep that in mind. Do your research prior to even booking your flight, this will really allow you to understand the prices of accommodation, excursions and dining and prevent you from going over budget or having to endure the feeling of missing out because the things you’d like to experience are too expensive.

So let’s get into the day by day activities of what I got up to in Hawaii and how I’d adjust to make the days even more seamless. Firstly, I boarded my flight from New York City to Los Angeles where I had a three hour layover then I boarded my flight to Honolulu. Where I stayed on the island of Oahu. Officially, there are 137 recognized islands that make up Hawaii, with eight main islands. Hawaiʻi, Maui, Kahoʻolawe, Lānaʻi, Molokaʻi, Oʻahu, Kauaʻi, and Niʻihau.

Day 1

You receive a lei once you arrive at the hotel.

Arrival day. After arriving at the hotel I checked in and went straight to my room to relax. A total of about 12 hours of travel left me exhausted! I had an amazing view of the ocean and to my surprise also a perfect view of the Friday night fireworks done by the Hilton Hotel. You can book a night cruise to view the fireworks show. My first day wasn’t a full day so after relaxing we headed to dinner at a restaurant called Eating Place. I’ll get into all the food I ate in my next blog post.

Balcony view

The hotel we stayed at was the Ritz Carlton Residences. My room was super spacious and was practically an apartment. It had a kitchen with plates and pots and cutlery. I loved how spacious it was and I had a soaking bath almost every night. It was so relaxing.

Day 2

This was my actual first full day on the island. We decided to walk the strip and go shopping. Our hotel was located in such a central location. We could literally walk to everything we wanted. Stores, restaurants, bars or the beach. The strip had a mixture of stores ranging from high end to even convenience stores. Day two was a Friday and on Fridays they convert the main road on the strip to a street market. They had local food, drinks, jewelry and even clothes for sale.

On the strip they had a duty free mini mall and can I tell you I had to restrain myself. They had such a variety of things on offer. I got some souvenirs and I was able to restrain myself from buying more perfume. I have a weakness for perfumes. We then moved on to some of the luxury shops and after a few of us bursted our budget we decided to get lunch. Lunch was at Cheesecake Factory. Generally, a very busy selection for tourists, we managed to get seated in about five minutes.

Street Market

After shopping we decided to return to the hotel to relax and cool down by the pool. The hotel had two pools, one for families with kids and an adult only pool. For me, this trip was not one for a lot of activities. I had already flew for about 23 hours from China to get to New York, and while I had a few days to relax I was still tired. About and hour at the pool did the body well after all that walking in the sun to shop. We rounded out the night at dinner at Herringbone. Which was walking distance from the hotel.

I feel like day two was a good day spent. Not too much was done and it allowed me to regain a bit more energy and relax a bit more. I would have loved to have taken a walk on the beach after eating lunch just to feel the sand between my toes, have a cold drink and watch the sunset. But alas we had dinner reservations so we had to get back in time to get ready for dinner.

Day 3

Mimosas are always a yes.

It’s time to start indulging in some activities. After all I am a proud tourist and vacationer. Day three was designated the beach day. We picked a beach and drove to it. There was a beach walking distance from our hotel, but it’s generally crowded. So thats why we opted to drive to another beach. If I remember correctly we drove to Kailua Beach. There was a hotel located on the beach and we were able to have lunch at its restaurant. Lunch was delectable, really enjoyed it.

While at the beach you can rent umbrellas and chairs from the hotel if you are a guest. Being that we weren’t we couldn’t, luckily we saw an empty umbrella so we quickly commandeered it and put out our towels. The feeling of the sand between my toes transported me to such a place of gratitude. I’ve longed to visit Hawaii and I was finally there. I put my feet into the ocean and I felt like that’s where I was supposed to be. I was happy and I felt blessed.

Kailua Beach

After we relaxed at the beach and I got a welcomed tan, we headed to our sunset cruise. We booked our cruise through our hotel but any excursions can be booked online from various websites or even as you walk along the streets you’ll see small booths that offer excursions. Sunset cruises can begin from about USD $70 upwards. You just have to look for one that’s in your budget or offers what you’d like to experience. Our cruise offered drinks and also a snack. I was still full from lunch so I didn’t have the snack that was included.

Sunset Cruising

We removed our shoes at the dock and boarded the catamaran. After safety tips we set sail. This was my first sunset cruise and it was such a sight. We got to see different areas of the island and we even got a great view of Diamond head Mountain. Many people hike the mountain to get a panoramic view of the island and ocean. If you love a hike with a spectacular view you should put it on your list of things to do when you visit Oahu.

The most perfect sunset.

The sunset was magical. After about 30-45 minutes of sailing we came up the location to watch the sunset. The catamaran slowed and eventually stopped and I sat in awe watching the beams of sun peak through the clouds. It was a heavenly sight. My only regret was that I was a third wheel on this trip and didn’t have my regular travel partner. As we set sail back to the harbor I laid back and put my feet up and soaked in the moment.

We were drained from a day of being both in the ocean and on ocean. It was a full day of ocean vibes, and I loved it. We then returned to our hotel and relaxed a bit and decided to cancel our dinner reservations and or PF Chang instead. Being exhausted or doing too much in one day was not what this trip was for so relaxing was always priority. So after a soak in the bathtub, dinner arrived and then it was off to bed.

Day 4

It was an early day, because we had an island tour booked. We got picked up from our hotel at about 8:30 a.m. This excursion covered about 4 main locations on the island and the one I was looking forward to most was Waimea Waterfalls. But our first stop was a viewing point called Nu’uanu Pali. The day we went was terribly windy in the morning and extremely misty. A hurricane was passing the island so certain area’s experienced a lot of rain.

View from the misty Nu’uanu Pali lookout point.

We then moved on to the Byodo Temple. This is a non-denominational Buddhist temple. It’s located at the foot of the Ko’olau Mountains and was dedicated to commemorate the 100th year of Japanese immigrants to the island. It was so beautiful to see. The lush landscape captured my attention and I was in awe looking at the mountains. Once you enter you can ring the bell for good fortune.

Byodo Temple

We walked around and had a look inside the temple. It was small but well kept. Then after souvenir shopping we boarded the bus and headed to our next stop. Chinamans Hat.

Chinamans Hat gets it’s name from as you may guess, it’s shape. Located on the east of the island it is an attraction many come to see when on island tours. It’s a quick stop, but if you go on your own you can spend time there and even have a picnic there and put your feet in the water. After that our next stop was lunch. We drove to our lunch stop where I ordered the garlic shrimp and rice. That shrimp was spectacular.

A view of Chinamans Hat island.

After lunch, Waimea Waterfalls was next. I was looking forward to this stop the most. We had to walk through a very lush scenery for about 15-20 minutes to get to the falls but it was worth it. This location is perfect to spend a full day, having a picnic, playing games and taking in all the flora and fauna. It’s just beautiful. Fun fact is that this area has been the scene for several movies.

Waimea Waterfalls

Once you arrive at the falls it’s mandatory you put on a life vest as the waters by the falls are deep. I welcomed that life vest with open arms, because Reneé is not a swimmer. I definitely need to change that. But nonetheless, I went right into the water without hesitation. It was cold but the day was hot so it felt refreshing once I entered. I really didn’t want to get out. I can just picture myself laying back and floating in the cool waters. It’s a busy location so it’s going to be packed more than likely when you visit, but we make due with what the day has to offer and just live in the moment.

The beautiful Waimea Waterfalls

We then made a quick stop at a macadamia nut farm and had a cool drink of coconut water then quickly moved on to the Dole pineapple farm.

Coconut water anyone?

One thing to note is, if you really wish to explore the pineapple farm, you should go without an island tour. You aren’t provided enough time to really explore the farm and indulge in the activities offered there. When you visit via the island tour it’s essentially to try the Dole whip, some corn and buy souvenirs. This was our last stop and we headed back to our hotel where we dropped our bags and you may have guessed it, went shopping again. The night ended with some food from Raising Cane and a warm bath. Told you guys I had a bath almost every night. LOL.

Garlic Parmesan Corn on the cob.

Day 5

This was our last full day. I began the day with some room service. Some very expensive room service I should say. Then I went to the pool to relax and grab a bite to eat until it was time to get ready for our Luau at Paradise Cove. Originally we were supposed to go parasailing in the morning, but because of the storm passing the island we had to cancel.

Sun kissed at the Paradise Cove Luau.

After about almost an hour driving through some heavy traffic we made it to Paradise Cove and checked in. Prices vary based on where you’d like to me seated. We opted for the middle range which was about USD$140. Once you enter you’re greeted with welcome drinks. At check in your given a card with USD$16 to purchase drinks.

Once you’re shown to your seats you can walk around and visit one of the many attractions available. Either their souvenir market, take a picture with a parrot or get a fake Polynesian tattoo. Before the main show there are two smaller shows then dinner and after the main show begins. Each performance was very interesting. Seeing the different dances that are associated with each Polynesian island was f. I enjoyed every performance but my favorite was from the fire dancers of Samoa.

The Luau was the perfect way to end our stay in Hawaii and it’s something I would definitely do again if I return to Hawaii. This trip was a dream come to reality and I’m grateful to have been able to experience this with one of my closest friends. I’ve provided a five day itinerary below to help you with your own travels. Until next time, let’s see where to next!

Suggested Itinerary

Day 1 – If you’re able to arrive early I suggest checking into your hotel, take some time to relax either in your room or by the pool. You can ask the concierge for restaurant recommendations or check online for places you’d like to eat. Also take the time to ask the concierge for your recommendations or book excursions you’d like from a day in advance. Next you can finish the day with dinner and drinks. The International Market place has several restaurants and bars to choose from.

Day 2 – This day I suggest you take the island tour. You can pick from whatever package that suits your needs. An island tour allows you to see places that you may like to revisit during your visit and spend more time exploring. Doing it early in your stay gives you ample time to revisit locations. Most island tours come with lunch included. After you complete the island tour you can return to your hotel and either relax or take the time to walk around and get familiar with the area you’re staying in. You could even get some shopping done.

Day 3 – I suggest going to the beach and going for a sunset cruise. Start your day early. Get to the beach of choice and enjoy the sun and ocean waves. You can also have lunch on the beach or close to the beach. I think it’s best to go to a beach close to your hotel so you will be able to return and freshen up to attend your sunset cruise. If you’re hungry after your cruise and have time you can grab a quick bite or have a nice dinner at Herringbone. They tend to seat patrons a little later than other restaurants.

Day 4 – Visit the Kualoa Ranch. I didn’t get to visit this ranch but I wish I did. The ranch offered different ways to explore it. Either by ATV, horseback riding or a tour bus. Kualoa Ranch is famous for films such as Jurassic Park, Jumunji, 50 First Dates among others.

Day 5 – A luau is a must when visiting Hawaii. And I think it’s the perfect way to close out your stay in Hawaii. Paradise Cove has a great luau but their are others on the island that are smaller and more intimate that you can choose from. Your last day can also include a morning excursion of your liking. Many people opt for surf lessons, scuba diving, snorkeling or even a shark dive.

One response to “How to plan a trip to Hawaii”

  1. Good read as always ❤️

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