Day 1 – Landing in Paradise
We landed in paradise and checked into the Outrigger Beachcomber in the heart of Waikiki where we planned on staying for four nights. After a smooth arrival, we took an Uber straight to the hotel and got ourselves settled in. We wanted something in the thick of it, where there were lots of shops, activities, and restaurants nearby. It was a great location for us to stay in, and there were a lot of families, and young couples staying at the same place.
The evening was low-key—just what we needed. We wandered around downtown Waikiki, soaking in the balmy night air and tropical buzz.
Day 2 – Climbing Completely Uphill at Koko Head Crater Trail
We kicked off the morning with a quick search for a nearby breakfast spot (Hawaiian coffee hits different!). The day’s highlight was the uphill climb at Koko Head Crater Trail—a sweaty but rewarding climb with panoramic ocean views that made every step worth it. It was a long path full of stairs, until it ascended to the top with wooden blocks. I had really good hiking shoes, so my ankles were protected and my feet was quite stable.
📍 Parking Lot: 423 Kaumakani Street, Honolulu, HI 96825
Definitely bring a ton of water with you if you’re going to climb to the top. Between my boyfriend and I, we both had two gatorades and two water bottles. We ended up drinking 3 out of the 4 bottles. While climbing, I saw many people sweating and having trouble breathing. It’s not an easy hike, so I would highly recommend taking it easy and not pushing yourself too hard; take breaks when needed, bring your appropriate gear, and bring enough water.
Afterward, we cooled off by jumping in the waters at Waikiki Beach, conveniently right across from our hotel, before grabbing lunch in downtown Waikiki. The water was amazing, so clear and relaxing. Though the waters were pretty crowded, we still found some space to enjoy. I do regret not buying us a floatie.
We rested up in the afternoon and picked up our Zipcar at 5 pm from Alohilani Garage. Then it was off to the West Coast to catch a golden Hawaiian sunset by the beach. He proposed to me, which ended up being a huge surprise. He made the happiest girl in the world!
Then, later that night, we celebrated his special birthday with a dreamy dinner at natuRe waikiki, a modern French Restaurant. The menu is shared below. The service was well paced and attentive, and they even ended up giving us a small treat as a way to celebrate his birthday and our engagement.
Day 3 – Garlic Shrimp and Giovanni’s Shrimp Truck
This day was all about adventure and slow cruising through the legendary North Shore.
I actually really miss driving with windows down, blasting music, and seeing double rainbows. Driving along the scenic coastline was gorgeous, while taking stops to grab coffee and bio breaks while looking at the views.
📍 Must-Stop: Giovanni’s Shrimp Truck in Kahuku (56-505 Kamehameha Hwy)
We got the shrimp scampi plate, which was the most popular. They give you a hefty plate with lots of shrimp and rice, loaded with garlic bits and butter. I wish we went back for a second time.
As a surprise, my partner booked one night at Halekulani Hotel: Luxury Waikiki Oceanfront Accommodations. We walked over with our luggage to this hotel and dropped off our stuff at the new hotel.
We explored hidden beaches, scenic lookouts, and found a quiet spot to just hang out and be present. After a long day, we capped it off with a comforting tonkatsu dinner before returning to Waikiki.
Day 4 – Seeing Sea Turtles in the Wild
The morning began with our 9:30–11:30 am snorkeling tour with Living Ocean Tours. I had booked this tour for my partner and I, which ended up being one of the most amazing experiences. They took us to an area called Sea Turtle canyons, where the turtles tend to frequent. We then jumped into the water, with floaties and went snorkeling. The scary part was that the waves were quite massive, crashing and rolling until we got acclimated to the weather. To be honest, it was kind of scary, but we got used to it and then was able to see the sea turtles swimming in nature, which was so cool.
📍 Check-in: 1125 Ala Moana Blvd Slip B1, Honolulu, HI 96814 (Kewalo Basin Boat Harbor)
Pro tip: Bring towels, sunscreen, swimwear, and your camera!
We spent the afternoon relaxing and rinsing off the saltwater glow before heading to dinner at Monkeypod Kitchen – Waikiki at 6:00 pm (thankfully we had a reservation). The sunset vibes, handcrafted cocktails, and locally-sourced dishes made it a chill and satisfying close to our second-to-last night.
Day 5 – Leaving Paradise
We took it slow in the morning while eating at the Halekulani breakfast, packed up our stuff, and checked out.
Left our hotel at 1:00 pm to make it to the airport for our 3:30 pm flight. The trip went by in a blur, but we left feeling sun-kissed, fulfilled, and with more memories than we can count.
