10 Days in Hawaii Itinerary: Oahu and Maui

We spent 10 days in Hawaii on two islands, Oahu and Maui and it was a fantastic way to experience Hawaii for the first time.

Below is our 10 day Hawaii itinerary.

This post has affiliate links which we may earn a small commission from if you choose to purchase, at no extra cost to you. Listed prices are quoted in USD and are estimates. More info: Disclosure

10 Days Hawaii Itinerary Oahu and Maui: Waikiki 4 nights and Kihei 5 nights

Time Period: End of November to the beginning of December.
Trip Type: Couples. This itinerary can perfectly work for families and friend groups.
Destinations: Waikiki, Oahu and Kihei, Maui.
Transportation: No car in Waikiki - relied on Uber. Rented a car with Hertz in Maui.
Hotel in Oahu: Aqua Aloha Surf in Waikiki. Mid range, basic. About a 10 minute walk to the beach. Hot breakfast buffet included. ~180 USD per night.
Hotel in Maui: Maui Sunset (condos) in Kihei. Has a pool, parking and just 1 minute walk to the beach. ~$300 USD per night.
Minimal excursions.

We flew to Hawaii from Los Angeles with Alaska Air and flew Hawaiian Airlines for the flight between Oahu and Maui.

Oahu Day 1: Landed 340 PM

We called an Uber from HNL airport to our hotel Aqua Aloha Surf, around $35 USD. 

After we checked in, we went to Rainbow Drive-In for some yummy local Hawaiian food and then walked on the beach for the sunset. Then walked around the main Waikiki strip.

Hotel: Aqua Aloha Surf

I chose to stay at Aqua Aloha Surf Hotel since the price was within our budget and 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.

Oahu Day 2: Surfing and Shopping

Waves looked pretty nice that day so we decided to rent two longboards for 2 hours (~$25 USD per board). We didn't need a lesson since we know how to surf, but if you need a lesson, they cost around $75 USD per person for a group lesson. If you have never surfed before or are a baby beginner, we highly recommend a lesson.

Waikiki beach is incredibly crowded and it can get dangerous when people try to surf without knowing how. 

We ate at Marugame Udon for lunch which was delicious! Then we walked around the strip and to the International Market. We also did some shopping to stock up on beach clothes like flip flops and rash guards. Many of the stores like Billabong and Hurley were having good sales. 

Then we rested at the hotel, and walked to the beach for sunset. For dinner, we ate at the Japanese Food Court. 

Day 3: North Shore Day Trip

We wanted to see the North Shore during our time in Oahu. Even though Pipeline wasn't quite in its peak yet, but we still wanted to go up there and check it out and escape the crowds of Waikiki for the day.

As we didn't rent a car, we booked an Uber and our driver took us on a mini tour, stopping at a very cute coffee shop called Green World Coffee Farm along the way. They roast their own beans on the premises and offer pastries, sandwiches and shaved ice as well as Kona coffee. 

Then he drove us around Waialua, Mokuleia and up to Kawela Bay before dropping us off at Bonzai Pipeline. It was like having our own personal tour guide for a few hours which was great as he was a born and raised Oahu local.

We had grabbed our Uber driver's phone number so that we could call him when we were ready to leave Pipeline. Since we were hungry again, he dropped us off at at an outdoor food truck court in Kahuku where the Sugar Mill is to get delicious poke from Ry's Poke Shack, shaved ice from Badabingsu and Hawaiian plates from Da Bald Guy. We also walked around checking out the shops. 

After we ate, we called an Uber to take us back to Waikiki. We went back to the hotel to freshen up and walked to the beach to watch the sunset one more. 

We had so much to eat for lunch that we just bought some cookies and fruit to snack on for dinner. 

Our Uber cost around $180 USD there and back, including the stops.

Day 4: Pearl Harbor Tour 

For our last day in Oahu, we went to Pearl Harbor. We booked a Pearl Harbor Tour from Waikiki, Basic Short Tour which included admission to USS Arizona Memorial and Visitors Center, a tour guide and round trip transportation from Waikiki.

It was an extremely humbling experience. I chose this option so that we can still have time at our own pace and we weren't interested in a full day excursion since it was our last day in Oahu.

We chose the 7 AM, 5 hour tour so we got back to Waikiki early afternoon. The waves looked nice in the afternoon, so we rented long boards again to surf a couple more hours in the afternoon. 

Then we went to the Happy Hawaiian Cafe for dinner for our last night in Oahu. 

Alternative option: Snorkeling at Hanauma Bay in the morning during the day and a dinner night show at Polynesian Cultural Center. Two touristy things to do, but classic Oahu excursions. We did not snorkel at Hanauma Bay since we planned to snorkel in Maui. 

Day 5: 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 HNL airport from Waikiki for about $25 USD. 

Kihei Airbnb

I rented a 1 bedroom, 2 bathroom condo at Maui Sunset with a pool and free on-site parking via Airbnb. For 4 nights, we paid $782.40 USD.

I loved the condo. It was very 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.

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, picking up at the airport. Originally, I rented a normal sedan Toyota Corolla or similar but the agent at the counter upgraded us to a Mercedes convertible for free.

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. 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 6: Exploring Beaches

In the morning, we made coffee and then walked to the beach, part of Waipuilani Park around 9 AM. It was a pretty beach and we could see the mountains across the way with windmills. The sand was also super soft, nice for beach walks. 

Afterwards, we hopped in our convertible and headed south to explore. We first stopped at Wailea Beach where the Grand Wailea Resort is on 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.

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

We knew we wanted to try snorkeling in Maui rather than Waikiki. In the afternoon, we rented 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.

I saw several people snorkeling at the southern point of Makena Beach so I headed in with my gear. As I was getting in the water, a local was snorkeling and he took me along with him. 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 at our condo to watch the sunset again.

Snorkel gear rental: $19 USD for a day

Day 7: Helicopter Ride

I surprised Yeison with a Doors Off West Maui and Molokai 45 minute helicopter tour. 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. This doors off helicopter experience was one of the most exhilarating and memorable things we have ever done together!

We purchased the video of the Doors Off Molokai 45 min helicopter tour and the photo, since we had such a great time, despite a rainy start. I recommend that if you can afford it, to  purchase the "front seat" guarantee. I sat in the back middle and though I was perfectly fine with being in the back middle, you definitely get a WAY better view on the sides or in the front. 

10/10 for the helicopter tour with Air Maui! Great music, great pilot, great commentary, overall I felt super safe and had a fantastic time. Seeing all the waterfalls cascading down the lush island made me feel like we were flying into Jurassic Park! 

Helicopter ride for 2 adults: $590 USD

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 8: Haleakala National Park and Paia

To visit Haleakala National Park for sunrise, I purchased national park tickets a month before on the Recreation.gov website. It cost $1 USD for the parking. 

If you want to see the sunrise at Haleakala National Park, they release tickets about 2 months in advance. Set your alarm because they sell out fast!

Sunrise tickets are for 3 AM and we left around 2 AM since it was a 1 hour drive from our condo. 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 back at the condo around 9 AM, we took a nap and made breakfast. Afterwards, we headed back up north. We had originally planned the Road to Hana but the weather wasn't great in the afternoon and we only had that Mercedes convertible, so we decided to just visit Paia. 

Paia

Paia is a cute surfside town and the starting point of the Road to Hana. It did feel very touristy and prices were crazy expensive. Parking was also crazy and we were lucky to find a spot after driving around for ten minutes. 

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 to watch the sunset on the beach.

Day 9: Iao Valley State Monument

Today was our last full day so we took it easy. We slept in, enjoyed coffee and breakfast in the condo, and then drove to ʻĪao Valley State Monument for a short walk on the Lookout Trail Loop. 

We only spent about 1 hour at the State Monument since the trail was so short. Afterwards, we visited the Maui Tropical Plantation. We didn't go on their zipline or tram or take their tour, but we walked around, visiting the shops. It was a nice place to visit, the grounds were beautiful. 

I highly recommend booking a tour since you can get a coconut demonstration and learn about the beautiful flora and fauna of Maui and Hawaii. 

Day 10: Fly to Los Angeles 

Our flight was in the late afternoon so we checked out of our condo and slowly drove over to the airport. We stopped at Regal Maui Mall to grab some food before returning our car and checking in for our flight. 

10 Days in 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. For our first time to Maui and our first time as adults to Oahu, we had a fantastic time. Our main goal was to surf at Waikiki, sightsee and just take it easy and relax.

This 10 days in Hawaii itinerary is geared for travelers who want exactly that. To relax, sightsee and take things at their own pace. We didn't stay at super luxury hotels or book a lot of excursions but we had the perfect mix of fun and relaxation.