Two Weeks in Waikiki
- Jess Choi
- Feb 17
- 2 min read
Turning 40 is a milestone worth celebrating, and what better place to do it than the beautiful shores of Waikiki, Oahu? For two weeks, I immersed myself in the vibrant island life, surrounded by family, breathtaking scenery, and unforgettable experiences.
Here are the highlights from my trip!
Beautiful Accommodations
We split our stay between three amazing places. The first week was spent at the elegant ‘Alohilani Resort Waikiki Beach, where the infinity pool and ocean views set the perfect tone for relaxation. Then, we moved to a Vrbo at Aston at the Waikiki Banyan, offering a cozy, home-like feel with the convenience of a kitchen. In the middle of my trip, I joined my cousins at Aulani, Disney’s magical Hawaiian resort, where we embraced the spirit of Aloha with incredible amenities and a touch of Disney magic.
Special Moments with Family
The best part of the trip was sharing it with my family. On the morning of my birthday, I watched the sunrise with my cousin—a peaceful and unforgettable way to start the day. I spent quality time shopping, eating, and exploring the Waikiki strip with my aunt, uncle, and mom, culminating in a breathtaking sunset dinner at Duke’s. My mom and I also embarked on a road trip around the island, soaking in the stunning coastal views and hidden gems along the way.
Learning About Hawaiian History & Culture
A visit to Iolani Palace was a highlight of the trip, offering a deeper appreciation for Hawaiian history and its royal past. Walking through the grand halls and learning about the monarchy gave me a richer understanding of the islands beyond their natural beauty.
The Food (A Story for Another Post!)
Of course, no trip to Hawaii is complete without indulging in its incredible food. From fresh poke to malasadas and everything in between, we tasted some of the best island flavours. Stay tuned for a separate post dedicated to all the delicious eats!

Poolside Relaxation & Sunshine
Between adventures, I made sure to spend plenty of time lounging by the pool, catching up on my reading, and basking in the warm Hawaiian sunshine. Whether at ‘Alohilani, Aulani, or our Vrbo, the poolside experience was the perfect way to recharge and fully embrace vacation mode.
Final Thoughts
Celebrating my 40th birthday in Waikiki was truly a dream come true. Hawaii has a way of capturing the heart, and I already can’t wait to return.
Have you been to Waikiki? What were your favourite experiences? Let me know in the comments!