Girls Getaway to Hawaii: Oahu and Maui Itinerary

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This past December, my friend Kat and I took a girl’s getaway to Hawaii to try to have some fun relaxation time at the end of the year. Kat’s parents had hotel points for us to use, so we are very grateful that they treated us!  When trying to figure out which Hawaiian island to visit, we settled on both Oahu and Maui. We wanted the historical experience of Oahu, but the relaxing scenery of Maui. We had a blast following this one week Hawaii itinerary!


Sunday: Arrival in Honolulu

Kat stayed the night with us in San Francisco Saturday and night prior to our early Alaskan Airline flight on Sunday morning. We started our trip in Honolulu on Oahu, because we wanted to get the historical site seeing out of the way before relaxing.

Ala Moana Center: Largest Open-Air Shopping Center in the World

We hadn’t really figured out what we were going to do on our arrival day, so we started by going to the Ala Moana Center. Our Uber driver told us it was the second largest mall in the US, but according to Google it is the 7th largest shopping center in the US, but the largest open-air shopping center in the world. We grabbed a bite to eat, and walked around.

Diamond’s Head Hike

Since we only had two days in Honolulu, we decided to know the Diamond’s Head Hike out of the way. Open from 6:00 am to 6:00 pm, this hike takes you up the side of a crater to see beautiful views of the Pacific Ocean and the city of Honolulu. The last time to enter the park is 4:30 pm, which is precisely when we arrived. It costs $1 per person on foot or $5 per car (we had taken an Uber), and even with Kat’s injured leg we made it to the top in no time!

Monday: History in Honolulu

Pearl Harbor Memorial

Our number one site for Honolulu was the Pearl Harbor Memorial Site.

The USS Arizona Memorial was built over the sunken ship, and you can only access it by boat. 1,300 free walk-in tickets are available on a first-come first-serve basis, and include a short video on the history of the site along with a ride over. The USS Arizona Memorial is currently unstable and under construction, but the boat ride will still take you up for a view of the site.

The Pearl Harbor Memorial visit was incredibly emotional. There are a few free museums for you to walk around, and the video you watch is heartbreaking. As mentioned, the USS Arizona Memorial was built over the remains of the ship, which still contains the bodies of over 1,000 crewmen killed during the Pearl Harbor attack.

You can also pay to see some of the additional memorials, but we chose not to for this trip.

Iolani Palace

For our next stop on Oahu, we went to the Iolani Palace, the only royal palace in the United States. The palace was previously used by the Kingdom of Hawaii kings and queens, before joining the United States. For $20, you get entrance to the palace along with a self-guided audio tour taking you on the main and second floors to learn about its past residents. Afterwards, you can explore the basement exhibits and see artifacts from the palace.

State Capitol

After our palace tour, we walked across the street to see the open-air State Capitol building. It was very deserted and the doors to the House and Senate were locked, but it was fun walking around.

Duke Paoa Kahanamoku on Waikiki Beach

We had to stop by the Duek Paoa Kahanamoku statue, a site that honors the Hawaiian who internationally popularized surfing. We then took a stroll along the gorgeous Waikiki Beach, and enjoyed the sunset.

Tuesday: Island Hop to Maui

On Tuesday morning, we took a Hawaiian Airlines flight to Maui. Most flights between the Hawaiian islands on this airline are $70-$100, and will be the best deal that you can find. If you are hopping between the islands, I highly recommend grabbing a Hawaiian Airlines flight. I got to choose the rental car, so we got a VW Beetle from Turo, a site that is similar to AirBnB but for cars. Follow my referral link for $25 off your first Turo rental.

Pa’ako Beach

We wanted a relaxing beach day, so we drove to Pa’ako Beach which is also known as the Secret Cove. While pretty, this beach is not good for swimming because of the waves here, so we just relaxed for a few hours before our evening show.

Lahaina Banyan Tree

Since we were in Lahaina before our magic show, we made a quick stop at the Lahaina Banyan tree, which is the largest banyan tree in the United States. We couldn’t find parking, so our stop was more of a drive around the tree before heading to the district where the magic show was.

Warren & Annabel’s Magic Show

Per my boss’s recommendation, we bought tickets to the Warren & Annabelle’s Magic Show in Lahaina. At $69 per person, this is an intimate show focused on close-up hand magic. You start your evening in a parlor room where Annabelle “the ghost” plays a piano while you enjoy appetizers and drinks. You are then shown to the theater, where you are entertained by Warren’s magic tricks!

My coach told me to reserve these ahead of time, but I ignored his warning and was worried when the show was sold out online. However, I called the show the morning of, and they were able to squeeze us in the back of the theater! It was very entertaining, and I’m glad we went.

Wednesday: Bracing the Maui Road to Hana

Road to Hana

With my rented Beetle, we were going to spend Wednesday tackling the main Road to Hana. We started the morning stopping at the Hana Picnic Lunch Company to grab sandwiches to go. The store clerk there convinced us to download the Shaka Guide App, and I am so glad that we did! This app absolutely saved us. The tour guide tells you about spots along the way, and gives advice on whether a place is worth stopping at or not. He also would tell us what we could skip to save time, and gave us history lessons during long stretches of driving.

I could definitely write an entire post on our Road to Hana trip, but in summary we visited the following sites:

  • Pai’ia Town (Grabbed lunch)
  • Kaumahina State Wayside Park (Where we ate our lunch)
  • Ke’anae Peninsula
  • Ka’eleku Cave and Lava Tube ($12 entry, includes flash lights)
  • Waianapanapa Black Sand Beach (Did a short hike overlooking the ocean)
  • Pools of Ohe’o (Seven Sacred Pools, where we did a hike to a bamboo forest)


Thursday: Beach Day on Maui

Beach Day on Kaanapali Beach

We needed at least one relaxing beach day and Kat wanted to see if she could swim on her injured leg. We tried a few other beaches that were a bit too busy for us, but we ended up at Kaanapali Beach which was absolutely perfect. It wasn’t too busy, and the waves were not too harsh for swimming. There was free parking, public restrooms nearby, and a convenience store where Kat picked up snacks and snorkeling gear.

I was still exhausted (from both the Road to Hana and life in general) so all I wanted to do was sleep. Kat went swimming quite a bit, and saw fish and turtles come right up to her! We also saw dolphins jumping in the distance.

Friday: Crater Views

Haleakala Crater Drive and Views

Since we loved our guide, we purchased the Shaka Guide for the Haledakala Crater as well to give us directions and history on different sites. We did not catch the sunrise, but did visit shortly before lunch. We drove to the top of the crater, where observatories are located, and we had a phenomenal view of the island from above the clouds. We did a few small hikes, and then ate lunch in town at the bottom before dropping off the car at the airport.

Overall, the trip was exhausting but so much fun. I almost needed a vacation after this vacation! Special thanks to Kat for inviting me along with her, and to Kat’s parents for funding our hotels. Also thank you to my work coach John, who basically wrote our Maui itinerary.

Girls Getaway to Hawaii: Oahu and Maui Itinerary via @travelafterfive There are so many things to do on a girl\'s getaway to Hawaii. On Oahu, you should do the Diamond\'s Head Hike, visit the Pearl Harbor Memorial, and check out the Iolani Palace and State Capitol. On Maui, visit Lahaina\'s Banyan tree and a magic show. Do the Road to Hana, and drive up to the Haleakala crater. Even consider a beach day on Kaanapali Beach!

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