Oahu & Maui: A 1 Week Hawaii Itinerary and Expenses

Even though we live in a tropical country with rainforest, beaches and mountains, we had always wanted to visit Hawaii together. Hawaii and Costa Rica get compared to a lot because of those things but they are nothing alike to be honest! We had the opportunity to visit Hawaii for 1 week so I came up with a nice 1 week Hawaii itinerary to experience two islands in one trip.

This 1 week Hawaii itinerary including travel days is very straightforward: 3 nights in Oahu and 4 nights in Maui. Below is our itinerary with expenses, please note this trip was before the pandemic so prices for flights, car rentals, hotels and food may be very different nowadays!

1 Week Hawaii Itinerary Oahu and Maui: Waikiki 3 nights and Kihei 4 nights

Here is the breakdown of our 1 week Hawaii expenses and our itinerary to see if it fits what you’re looking for. Yeison and I are somewhat adventurous travelers who like to plan things ourselves and explore, we’re not super interested in doing lots of excursions since we don’t like to get too crazy with limited time.

We decided to spend 3 nights in Waikiki on Oahu and 4 nights in Kihei on Maui. We did not rent a car in Waikiki, but we did rent a car in Kihei.

Our trip was at the very end of November/beginning of December.

Oahu Day 1: Waikiki 3 nights

We flew in from LAX and landed around 3:40 PM. We Ubered to our hotel in Waikiki from the airport ($~24 USD). After checking in, we walked to Waikiki and the main strip to check it out.

Even though it was Yeison’s first time in Waikiki, he was more interested in walking around the beach, surfing and eating a lot of good food so we didn’t do many tours or excursions – just one very special one on Maui.

Hotel: Aqua Aloha Surf

I chose to stay at Aqua Aloha Surf Hotel for 3 nights. The price was within our budget and it was less than a 10 minute walk to the beach. We had a nice view of the mountains and the canal.

For 3 nights, we paid $466.47 USD with breakfast included. It was clean, not too loud and the staff was friendly. Their breakfast was very much Asian style with more Chinese/Japanese dishes which I didn’t complain about, but some other people may not be so keen on.

Waikiki Day 2

We decided to walk Waikiki end to end to experience the famous Waikiki Yeison’s seen on so many Youtube videos and movies. I had not been to Waikiki since 2002 and it was insanely different after 17 years!

Along the way, we would stop and sample cookies from the Honolulu Cookie Company, got some shaved ice and poke. We sat on the beach for awhile, watching the MANY tourists and surfers.

For dinner, we went to Rainbow Drive In which was a fun experience. The loco moco was huge and the mac salad was delicious. I was so happy we walked there because we definitely inhaled way more than our daily calorie intake for the day. We walked back to the main strip of Waikiki to watch the sunset, check out the stores, people watch and eat more cookies.

Waikiki Day 3

Yeison decided to rent a surfboard and surf a bit at Waikiki beach. The surfboard rental cost $25 for 2 hours. He had a lot of fun even though it was very crowded.

Afterwards, we took a nap and then went to Haili’s Hawaiian Foods for some local food. It was reasonably price and delicious.

Then in the evening, we headed back to the main strip to walk more, watch the sunset and do some shopping.

Day 4: Fly to Maui

On day 4, we flew with Hawaiian Airlines to Maui for our second half of the vacation, arriving at 630 PM. I chose Kihei to stay on Maui since it had very reasonably priced Airbnbs, it was in close driving distance to the places I was interested in going and I did not want to stay at a crazy expensive resort.

Our flight cost $159.98 USD for both of us. We Ubered to the airport ~$24.59.

Kihei Airbnb

I found a 1 bedroom, 2 bathroom condo rental just a 5 minute walk to the beach with a pool and free on-site parking. For 4 nights, we paid $782.40 USD. The Airbnb was located in the Maui Sunset Condos.

I very much enjoyed the condo, it was clean with a fully stocked kitchen and bathroom amenities. They also had beach chairs, boogie boards and beach/pool towels for use. I loved that it was a 5 minute walk to the beach, it was wonderful to watch the sunset from the beach every night as we don’t live near the beach in Costa Rica.

The location was awesome. 25 minutes from the airport, 7 minutes to Safeway and 20 minutes to the popular beaches and resorts.

Kihei Car Rental with Hertz

I booked a car rental with Hertz through Hotwire. Originally, I rented a normal sedan like a Toyota Corolla but the agent at the counter upgraded us to a Mercedes convertible. We were NOT expecting that all but we started talking to him about tourism and he just seemed glad to talk to someone and offered us this upgrade.

To be honest, it was fun to drive this tiny Mercedes convertible coup for like a day. Afterwards, I got a bit annoyed by how low it was since we are very used to driving rugged vehicles. But we made the best of it, put the top down and enjoyed the classic Maui convertible ride.

The cost was $276.58 USD with full insurance for 5 days.

Day 5: Exploring Beaches and Snorkeling

First thing we did in the morning was make coffee and then we walked to the beach, part of Waipuilani Park. It was a pretty beach, nothing spectacular but we could see the mountains across the way with windmills and the sand was very soft.

Afterwards, we hopped in our convertible and headed south to explore. We first stopped at Wailea Beach (peeking at the Grand Wailea Resort, wow) to check it out and then kept heading south. We parked near the Big Beach third entrance but first walked to Makena Cove. This beach was tiny but GORGEOUS. And compared to how busy Wailea and Big Beach were, we were the only ones at Makena Cove. Just one other guy was there snorkeling and he left shortly after we arrived. I took so many pictures!

Afterwards, we walked back to Big Beach part of the Makena State Park. We walked all the way to the northern end to Little Beach, a clothing optional beach.

Snorkeling Kihei, Maui

I saw several people snorkeling at the southern point of Makena Beach. Since I love snorkeling, I really wanted to try it in Maui. We grabbed snorkel gear from Snorkel Bob in Kihei, as well as lunch at Coconut’s Fish Cafe for the best fish tacos I’d ever had.

After we filled up, we drove back to Makena Beach to do some snorkeling. Yeison decided to stay behind and although I’m a fairly experienced snorkeler, I am always super cautious in new spots. Luckily, a local was snorkeling and he took me along. We saw five turtles and SO many fish! It was amazing to see so many turtles close to shore.

After snorkeling, we went back to the condo to freshen up and walked to the beach to watch the sunset again.

Snorkel gear rental: $19

Day 6: Helicopter Ride

Day 2 on Maui was a very special day. I surprised Yeison with a doors off helicopter ride to see West Maui and Molokai. I read and researched a lot on helicopter rides in Hawaii and Maui was a better choice for us since we were more interested in seeing the nature, not the city (like the Waikiki helicopter rides).

Unfortunately it sprinkled and was quite cloudy at the start of our ride but then it cleared up and it was a spectacular experience. I’m very scared of helicopters and small planes but Yeison was like a little kid on the last day of school. This doors off helicopter experience was one of the most exhilarating and memorable things we have ever done together!

Helicopter ride for 2 adults: $590 USD. This was definitely a splurge. Since we literally never take tours or splurge while traveling and I knew this was something Yeison would love 100%, I felt fine to splurge.

We spent the rest of the day relaxing at the condo, walking on the beach and watching the sunset. We headed back to Coconut’s Fish Cafe again for more fish tacos for dinner.

Day 7: Haleakala National Park

Today we woke up super duper early to see the sunrise at Haleakala National Park. It was a 1 hour drive from our condo so we left at 3 AM to get there at 4 AM. Sunrise was around 630 AM but I wanted to make sure we got a good spot. I am glad we went early because by around 5-530 AM, it was absolutely packed. We got a front and center seat, being one of the firsts to arrive.

It was worth waking up crazy early and standing in freezing temperatures to watch the sunrise at Haleakala National Park. As we stood above the clouds, watching the sun rise above them, flashing beams of brilliant gold lights, a surreal feeling completely washed over me. It was magical to be there with a crowd of people who were all experiencing the same intense moment, as everyone stopped talking and just watched in awe as the sun peeked up above the clouds.

After the sun fully came up, we drove back to do our condo, driving slow to enjoy the views as we descended down the mountain. It was absolutely nuts that we were driving from freezing temperatures on top of a mountain at 3000+ meters down to sea level at 80 F in just 1 hour!

When we arrived at the condo, we took a nap and made breakfast. Afterwards, we headed back up north. We had thought about doing part of the Road to Hana but with only just 1 day, we decided to save it for a future trip.

Paia

Instead, we visited Paia which is the starting point of the Road to Hana. We spent the next couple hours checking the town. Paia was a cute surfside town. However, it felt quite touristy and prices were more expensive. *Parking is crazy limited in Paia so I recommend getting there early.*

We decided to drive a bit up north to see some of the beaches on this side of the island and we stopped at Ho’okipa Beach Park. There were several cars parked at a lookout point, so we pulled over and walked over to see Ho’okipa Beach. This beach was gorgeous and there were a lot of people surfing. We also saw a bunch of turtles hanging out with the surfers!

As Jaws just ended two days before, there were still a lot of surfers hanging about. It was really fun to see all the legit surfers hanging out everywhere.

After Ho’okipa Beach, We decided to drive back to our Airbnb for our last night, pack and get ready to go home.

Day 8: Fly Out. End of 1 Week Hawaii Itinerary

Our flight was not until 5 PM that day. We checked out around 9 AM and drove to ʻĪao Valley State Monument. Short walk but beautiful views. We spent about 1 hour here.

Afterwards, we headed to the Regal Maui Mall where we grabbed lunch and also watched a movie (Wreck it Ralph 2).

Then we returned the car and checked in for our flight home.

1 Week Hawaii Itinerary Expenses

Here are the rest of our expenses for this trip.

Flights: LIR – LAX (stayed 3 nights) – Honolulu – Maui – LAX (stayed 1 night) – LIR $1447.51 USD total for 2 people. I used my Alaska Air companion pass.

Shopping: $80.64

Food: $780 USD total

Our complete total expenses of our Oahu and Maui itinerary was $4661.17 USD total for 2 people for everything. Obviously we did not travel on a tight budget but neither did we splurge heavily or travel luxuriously. I’d say this was fairly average for back then for 2 people, 1 week in Hawaii which is not a cheap destination. Flights were very expensive for us coming from Costa Rica and we did decide to spend some nights in LA but thank goodness we used our companion pass.

Nowadays after the pandemic with rising travel costs and inflation, I’d say you would need to spend more for this same trip since nearly everything has increased in prices.

1 Week Hawaii Itinerary Thoughts

I would not have changed our itinerary after our visit. We were happy with the amount of time we spent on each island albeit it a bit short. I had visited Oahu several times before in my childhood so I was keen to see Maui. Yeison had never been to Hawaii and he really liked Waikiki, despite how crowded it was.

If we were ever to visit Oahu again, we will spend at least one full week. Furthermore we would like to rent a car to see more. I especially want to go to the North Shore to watch the Pipeline surfers (a bucket list goal of mine to see). *Funnily enough, the next year we visited Japan and Korea with a 1 day layover in Oahu. Read our blog post to see how we spent 24 hours in Oahu.*

I am not sure if we will visit Maui again. Personally, I loved Maui’s beaches and nature but the vibe was very different to Waikiki. It felt way slower with a lot of mainland retirees in our condo complex. In general, it felt a lot less diverse than Oahu.

Overall, we had a fantastic first trip to Hawaii. If you are also a first time visitor, have 1 week and want to visit two islands, we hope this 1 week Hawaii itinerary blog post was helpful for your to get your travel planning started!