Five Days in Oahu:
Day 1: Arrival and Relaxation
- Hale Koa Resort
- Monkey Pod Restaurant -Waikiki
Day 2: East Shore adventure
- Ho’omaluhia Botanical Garden
- Cinnamon’s Restaraunt, Kailua
- Waimanalo Beach
- Halona Blowhole
- Hanauma Bay State Park
Day 3: North Shore Adventure
- Leonard’s Bakery
- Dole Plantation
- Hale’iwa
- Laniakea Beach
- Waimea Valley
- Ted’s Bakery
Day 4: Resort Fun
- Waikiki & Luau
Day 5 -Diamond Head and Dinner
- Diamond Head
- Marugame Udon
I recently spent five days on Oahu for my 50th birthday, and while I wished the trip had been longer, I was surprised by how much I was able to see and do in such a short time. It had been 15 years since my last visit, and I was eager to revisit old favorites while discovering new gems.
Oahu, the third-largest Hawaiian island, is home to a vibrant mix of natural beauty, rich culture, and modern amenities. Most of the island’s population is centered around Honolulu, where the majority of accommodations, including the iconic Waikiki Beach, can be found.
We stayed at the Hale Koa Hotel on Waikiki Beach, a resort exclusively for military members and their families. If you qualify, it’s an incredible, family-friendly place to stay. For non-military visitors, there are plenty of other fantastic hotels along Waikiki Beach, which also serves as a central hub for exploring the island.
Here’s a detailed look at how we spent five unforgettable days on Oahu:
Day 1: Arrival and Relaxation
We landed in the early afternoon, picked up our rental jeep, and headed straight to the Hale Koa. Feeling jet-lagged, we spent the day unwinding by the pool and enjoying Waikiki Beach.
Dinner at Monkeypod Kitchen
For our first dinner, we dined at Monkeypod Kitchen in Waikiki. This open-air restaurant offers delicious food and award-winning drinks. Do yourself a favor and order their famous Mai Tai—it’s a must-try.
Day 2: East Shore Exploration
Our second day was packed with natural beauty and unexpected stops.
Hoʻomaluhia Botanical Garden
Located about 45 minutes from Waikiki, this lush garden in the Koʻolau Mountain Range is free to visit and takes about 1-2 hours to explore.
Cinnamon’s Restaurant, Kailua
This local favorite is perfect for breakfast or lunch. We loved the Tropical Stuffed French Toast, the Lilikoi Chiffon Pancakes, and the Poke Bowl.
Waimanalo Beach
A tranquil, turquoise paradise on the east shore where we lounged on a secluded stretch of sand.
Halona Blowhole
We quickly stopped on our way back to Waikiki to admire this natural wonder on the southeast shore.
Hanauma Bay State Park
Sadly, we arrived just after closing. This was a good reminder to start early, especially when visiting popular spots.
Day 3: North Shore Adventures
We dedicated this day to exploring the iconic North Shore, using the GuideAlong app to find must-see stops.
Leonard’s Bakery
A pre-road-trip stop in Honolulu for their famous malasadas—pillowy, sugar-coated perfection.
Dole Plantation
Originally a pit stop, we enjoyed a walk around the grounds and indulged in a classic Dole Whip.
Haleʻiwa & Matsumoto’s Shaved Ice
This charming town is home to shops, restaurants, and the iconic Matsumoto’s Shave Ice.
Laniakea Beach (Turtle Beach)
Known for its resident turtles, you can snorkel with them or watch them bask on the sand.
Waimea Valley
The $25 admission is worth it for the botanical gardens, serene canyon, and swimmable waterfall at the end of an easy hike.
Ted’s Bakery
For me, this is a nostalgic favorite. I fell in love with Ted’s Bakery when I visited 15 years ago. Ted’s serves incredible baked goods (don’t miss the Coconut Cake or the Chocolate Haupia Cream Pie ) and delicious meals like spicy garlic shrimp.
Day 4: Waikiki Beach Day and Luau
After two busy days of exploring, we took a relaxing day to enjoy Waikiki Beach and our resort. In the evening, we attended the Hale Koa Luau, which I highly recommend for its authentic performances and delicious food.
Day 5: Diamond Head and Dinner
For our last day, we kept things simple with a mix of activity and leisure.
Diamond Head Hike
This iconic 1.5-mile hike rewards you with phenomenal views and fascinating military history. Be sure to make a reservation before heading out.
Marugame Udon
Our final dinner was at this popular Japanese noodle spot in Waikiki. Despite the line outside, the service was quick, and the food was incredible—perfect for a casual but memorable meal.
Final Thoughts
Five days may not seem like much time, but we were able to strike a balance between adventure and relaxation, making the most of every moment. Oahu offers something for everyone, from breathtaking beaches and lush gardens to vibrant towns and rich cultural experiences. Whether you’re planning your first visit or a return trip, this itinerary is a fantastic starting point for creating your own unforgettable Hawaiian adventure.
If you are looking for more Hawaii posts, be sure to check out my post about Napili Kai, our favorite resort on Maui.
Mom of two and seeking sanity in the everyday. Let’s chat about family, school struggles, travel, and living our best life. Located in the San Francisco Bay area.
