5 day trip itinerary and things to know before you go!

Table of Contents

1. Best time to visit

2. Where to Stay

3. What to Pack

4. 5 Day itinerary

5. Other activities

Best Time to Visit

Honestly there really isn't a bad time to visit Hawaii however if you want to avoid the crowds and have the best weather April - May and September - October are your best bet. The summer months are typically less crowded as well! We visited around Thanksgiving break and experienced some rainy days and crowds around Waikiki.

Where to Stay

I would recommend staying in Waikiki. It has the best restaurants and is a good central hub to get to around to all the best spots. It is expensive to stay anywhere on the island especially with all the resort fees and parking expenses. We stayed at the shoreline hotel with my credit card points otherwise air b n b is also a solid option. I'll list some of the other hotels we were also considering and a hostel option for a true budget friendly experience which is typically always me.

How to get around

I highly recommend renting a car! It's so worth it to splurge in order to see every part of the island. We decided to do less paid activities and more hikes and beach days to justify the car rental expense. There is some public transport, but it makes it more difficult to get to more specific places. We rented from budget car rental and ended up costing around 400 for 5 days! Also be prepared to have to pay to park every night at the hotel or air b n b you stay at.

What to Pack

Reef safe sunscreen - you'll want to apply multiple times a day because Hawaii sun is very harsh! It's also required to have the reef safe sunscreen.

Swimsuits - gotta pack lots of swimmies for the insta pics and for beach days

Lightweight jacket - for rain or when it gets a bit more chilly in the evenings

Backpack / tote bag - it's so nice to have all your belongings in one large bag or be able to day hike with all the essentials

Flip flops/ slip ons - have to have beach shoes to make it easier to get sand off when traveling around

Hiking shoes - if you enjoy hiking bring proper footwear! I just brought my hokas and they served me well for the short hikes we did

Camera gear - I brought my canon 5d mar IV and a mavic mini with me! A film camera would've also been amazing

Reusable water bottle - make sure to stay hydrated especially being in the sun all day

5 days in Oahu

Day 1: Arriving

Arrive at the main airport at Daniel K Inouye International Airport and pick up your rental car so you'll be set for your trip
Watch sunset anywhere along the beach in Waikiki. It will be crowded there but it's perfect to be close to town so you can easily check into your hotel
Eat yummy food! we ate at the hotel restaurant at Heavenly to make it easy, but there was a udon noodle place that was packed every night named marugame udon
Get some good sleep for an adventure packed day!

Day 2: East Side

grab coffee at island vintage coffee in Waikiki before your day trip
Start the day by visiting the Hoʻomaluhia Botanical Gardens this was one of my favorite places we went to since I'm such a nature girl
Head to Kualo ranch where jurassic park was filmed for an adventure! They have atv tours, horseback riding, and movie site tours
Secret Island and China Man's Hat is close to Kualo ranch so stop by an hour before sunset! The famous dock where 50 first dates was filmed is along secret island. Definitely the prime instagram photo spot. We used google maps to find the dock landmark and walked along a hidden trail to find it!

Day 3: North Shore

Have to start the day getting coffee and surfers coffee is there spot in between Waikiki and the North Shore
Drive an hour and a half to have a full beach day along the North Shore! It's arguably one of the most beautiful places on the island
Sharks cove to snorkel and swim, the waves on the rest of the beach don't allow swimming due to it being dangerous so this is the place to swim
Banzai pipeline to see some of the best and most intense surfing! Don't attempt to surf unless you're ver experienced! We enjoyed watching all the surfers shred
Sunrise shack for an acai bowl and then go to the food trucks for some tacos and shaved ice
Save Waimea beach for Sunset or to hang during the day in between as well

Day 4: Big hike or another small hike/ beach day

If I were to go back I would hike the legal side of the stairway to heaven! I heard it takes all day however it is a bucket list hike!
Other hike options: Lanikai pillbox, diamond head (reservation required), manana ridge trail
If you're not into hiking we did the pillbox and Lanikai beach on this day after our sister sunrise shoot

Day 5: Waikiki day and Lanikai

Parasailing or helicopter tour for an adventure
Enjoy one last beach day anywhere along Waikiki
Happy hour boat tour Na Hoku 2 is what we did! It was 40 dollars for all you can drink for an hour. The crew was so sweet and it was the perfect way to see a different perspective of Waikiki
Continue the happy hour at Monkeypod! they had the best happy hour on the island and we even went twice. They have $12 pizza, half off appetizers, and drink deals
Make sure to go to Lanikai at least once on your trip. I think it was the most beautiful beach on the island and pillbox hike is super close by

Other fun activities to fit in:

Learn to surf! Waikiki is great for beginners and group sessions are around $85 and up
If you're not on a budget like we were a helicopter tour sounded insane. It's $395 per person so we decided to pass this time
Rent snorkel gear to see some wildlife in the ocean you can book a tour or just rent the gear and find a place near the shore
Swim with sharks in an underwater cave!