Hawaii is a gem that has captured my heart from my first visit back in May 2021. I was fortunate enough to go back and explore something different every year since then. Working remotely for ~2 months in Hawaii is a time I’ll never forget. With my latest trip, I curated a one week itinerary to explore all parts of Oahu and shared what I loved with my mom and my youngest brother. I’m here today to share that with you! All food trucks and restaurants mentioned below (details here) are delicious and will not disappoint!
A common question I get asked from my friends when traveling is how long to stay in a particular area. The answer is that it depends on the type of trip you want to experience and what you want to do with your time. I personally chose to do a week with my family on one island because 1. I’m working remote and 2. traveling back and forth would’ve been more planning and we’d rather stick to one place to explore more of it.
We are a fairly active family and love to explore. Feel free to omit activities / food recommendations as you see fit. Scroll all the way down for the TLDR itinerary download file.
Without further ado, here’s my one week Oahu itinerary:
Thursday, Day 1: Arrival
- Arrive at HNL and pick up car rental
- Download offline map of Oahu: not all areas of the island has strong service
- Drive to airbnb/hotel in Waikiki and drop off luggage
- Stop by Foodland or Costco and pick up essentials (sunscreen, whatever you forgot to pack, snacks, etc)
- Dinner reservation: Yoshitsune
- Reservation highly recommended, as a long wait time is expected during peak dining hours
Having a car was essential because I wanted this trip to encompass more than just exploring Waikiki and Diamond Head. Taking an Uber around could work (I did it on a previous trip), but that gets expensive. If you do end up renting a car, make sure to check on the parking situation at the airbnb/hotel.
I went with an airbnb in Waikiki as our base because 1. convenience – close to the beach and walkable to restaurants/shopping, 2. free parking, and 3. familiarity.
Friday, Day 2: North Shore
- Pack a mini go bag: sunscreen, snacks, filled up water bottles, hat, sandals, sunglasses, battery pack, etc
- Grab coffee and pastries at Coffee Gallery
- North Shore – Haleiwa shoreline fishing
- Ka‘Ena Point State Park is ~5.6 miles hike – navigate to Ka‘Ena Point Trail Parking
- Buy fruit from local vendors
- Giovanni’s Shrimp Truck
- Matsumoto Shave Ice
- Dole Plantation or stop by food truck for Dole whip
- Ono Seafood
- Waikiki Beach
- Tonkatsu Tamafuji – make a reservation or walk-in (we waited ~1.5 hrs)
What looked to be a potentially gloomy and rainy day turned out to be beautiful sunny day as the sky was clearing up! We started our day early. I worked remote from Coffee Gallery while my brother went shoreline fishing and my mom walked along the beach. Highlight activity of the day is the hike; the views are stunning with dramatic, lush mountains right next to the sparkling turquoise waters.
Saturday, Day 3: Waikiki Surf and Lūʻau Day
- Kona Coffee Purveyors | b patisserie
- Early morning 5k run – Ala Wai Seaside
- Surfing lessons 8AM – 10 AM
- Kaka’ako Farmers Market (8AM -12PM) – shop and grab lunch
- Foodland Poke
- Golden Pork Ramen Bar (skipped because too full)
- Chill at Waikiki Beach
- Paradise Cove Lūʻau
My mom’s one request for the day was to go to the farmer’s market. We all loved it, and it was perfect timing to go after our surf lessons. My brother and I were famished from baking in the sun all morning and paddling, so we stuffed ourselves with meat and veggie wraps, desserts, fruits, and Kona coffee. KCC Farmers’ Market is another option, but we ran out of time.
Sunday, Day 4: Kualoa Ranch & Hoʻomaluhia Botanical Garden
- Morning coffee at Kai Coffee
- Drive to Kualoa Ranch & pick up Leonard’s Bakery en route for pre-activity fuel
- Horseback tour / UTV tour / E-Biking tour
- Variety of packages
- Lāʻie Point State Wayside (skipped because of weather)
- Yummy Huli Huli Chicken
- Byodo-In Temple & Hoʻomaluhia Botanical Garden (skipped because of weather)
- Marugame Udon
Sunday was the most rainy day. If it rains while you’re here, exercise caution, as roads were blocked due to floods and mudslides.
Monday, Day 5: Kailua Beach & Waikiki
- Coffee + breakfast at Kai Coffee
- Lanikai Pillbox Hike – parking is limited; the sunrise hike here is so worth it
- Kailua Beach Adventures
- Twin Island Guided Kayak Tour OR
- Beach Package
- Island Vintage Coffee Waikiki
- Shopped around Waikiki
- Musubi Cafe Iyasume
- Matcha Cafe Maiko
My weekdays are more limited because I work remote. If you’re not working remote and want to start early, I highly recommend a sunrise hike at Lanikai Pillbox. Start early (5AM) and bring your camera for that stunning sunrise shot. Parking is limited, so the earlier the better. Bring a flashlight.
I highly recommend the twin island guided kayak tour if you’re exploring Kailua with Kailua Beach Adventures. I went on the tour during one of my previous visits, and it was such a blast! You’re exploring different parts of the island and you get in a great workout! It is quite strenuous though, so I opted for the beach package this time. I personally did not think the beach package was worth it, but I got it for the convenience; parking, lunch, bike, beach, and snorkeling gear are all provided. If you bike out to the beaches further away from the main store, I recommend locking up your bike near the beach entrance. Someone stole my bike seat since I locked mine out closer to the road with other bikes.
Tuesday, Day 6: Diamond Head Hike
- Shark Diving or Oahu Shipwreck Dive (skipped this trip)
- Diamond Head Hike
- Sushi Sho Bento
- Waikiki Beach Day
- Wine night
If you’re into diving or snorkeling, there are some great spots around Oahu. I did my first open water deep dive here in Oahu on a previous trip, and I felt like I was in another world.
Wednesday, Day 7: Koko Crater Tramway Hike & Pearl Harbor
- Koko Crater Tramway Hike
- Leonard’s Bakery Food Truck
- Pearl Harbor
- Pack and get ready to leave the next morning
Hiking the Koko Crater Trail is quite an experience! My mom definitely wanted to give up half way up, but she powered through and made it to the top (so you can too). What makes it memorable is the stunning panoramic views of Oahu’s southeastern coastline and the surrounding landscapes.
That’s the end of our trip! There’s tons more I wanted to show them, but I know we’ll be coming back again sometime soon. If you haven’t explored Oahu, I highly recommend adding it to your list. Trust me – you won’t be disappointed.
TLDR of itinerary:
If you read any of this and made it to the end – thank you! If this post inspired or positively influenced your future Oahu trip in any way, please reach out via email or instagram and share with me!
Discover more from Wen & Where
Subscribe to get the latest posts sent to your email.