4-Day Itinerary in Oahu for Couples
Happy twelve years to us! We decided to treat ourselves to 4 kid-free days in paradise.
A couple years ago, we took our whole family to Mexico to celebrate a decade of being married. This time, we hopped on a plane all by ourselves! In fact (this is sad to admit), this was THE VERY first time Patrick and I had ever gone on a vacation of this magnitude without our kids.
Normally, Patrick and I get to focus on just the two of us throughout the year via date nights or the occasional 24- to 48-hour getaway, but we had never vacationed together without our spawn in tow. This time we not only left our state, but crossed the Pacific Ocean!
Where We Stayed
Interior view from entrance hall. Interior view from lanai.
We wanted a beachfront property on Oahu that was centrally located, and the Outrigger Waikiki Beach Resort was the perfect fit. The room was comfortable and though we didn’t choose an ocean-view room, we still could see a bit of the Pacific from our lanai.
View to towards shops. View towards ocean.
I had been to Oahu before but this was Patrick’s first time, so I planned an itinerary for us that included hitting up most of the iconic stops and a drive around the whole island! As always, there is never enough time to do all the things we wanted to do, but we sure packed in a lot of fun in just four days:
Day 1 – Afternoon Hike
Our flight arrived in the early afternoon. After getting settled into our hotel room and grabbing a quick bite, we headed straight to Diamond Head for a hike. The hotel offers you free access to the trolley system that takes you to numerous places around the vicinity, including Diamond Head.
View to the northeast. View to the southwest.
After our hike, we headed back to the hotel and freshened up before taking a night time stroll along Waikiki Beach.
We finished off our first day by walking across the street to the International Market Place and having dinner at Eating House 1849.
Day 2 – Resort Day
The second day was set aside for resort relaxation. We literally did not want to go anywhere or do anything … and that is exactly what we did!
We woke up early to claim our spot for the day by snagging a couple beachfront lounge chairs. While we waited for Duke’s Waikiki to get set up for breakfast (it is located right in the Outrigger Waikiki Beach Resort), we sat on the beach to watch the sun rising.
After a yummy breakfast we lounged. We swam until our fingers got wrinkly. We lounged some more. GLORY.
When our stomachs started grumbling again, we headed upstairs to Hula Grill for lunch, where Patrick tried to mimic the Mai Tai man’s face the best he could, LOL.
We topped it off by killing a Hula Pie from Duke’s.
Eventually, we got our lazy bottoms up in the late afternoon to embark on a super fun sunset cruise aboard Waikiki’s newest catamaran, The Holokai, which offered ah-mazing night views of the Waikiki coastline.
For dinner, we grabbed some food from Pau Hana Market which is a food truck park with outdoor seating.
Day 3 – Exploration Day
This was exploration day and we rented a Jeep to drive around the whole island! After fueling up bright and early at Rainbow Drive-In, we stopped at Pali Lookout, which offers sweeping views of Oahu’s windward coast. Apparently, it is the site for one of the bloodiest battles in Hawaii’s history!
One of Oahu’s iconic eats. Breakfast Special.
We then headed to Kailua to take a morning stroll along its white sand beach and turquiose blue water … significantly more beautiful and pristine than the beaches of Honolulu.
We continued northbound, along the eastern coastline (where you can also visit Kualoa Ranch), and grabbed lunch at Giovanni’s Shrimp Truck.
Giovanni’s! Shrimp Sampi Plate.
We then rounded the northern “tip” of the island and made our way down North Shore, stopping at all the iconic beaches that made this part of Oahu famous. The weather didn’t provide the kind of winter swells that breed a whole lot of excitement but we still enjoyed getting to see surfers in action at Pipeline. The Vans Triple Crown kicked off on this day, so it was a super special treat to experience that for a bit!
When we were done beach-hopping, we grabbed some shaved ice from Matsumoto’s before heading south to Pearl Harbor. All I can say is, “WOW”. I had been there before as a teenager but experiencing this as an adult was something else … more solemn, more emotional, more in respectful awe of this part of our nation’s history.
Then it was back to Waikiki for dinner!
DAY 4 – Morning Snorkel
This was our last day and we intentionally booked a late evening flight so that we could maximize our time.
We wanted to beat the crowds at Hanauma Bay, so we ventured from our hotel early in the morning. We were pleasantly surprised to find out that if you arrive before 7 AM, not only do you score coveted parking but you also bypass any fees. Free snorkeling for the win!
After swimming around for over an hour with fish, we hit up Makapuu Point Lighthouse Trail for another hike. Personally, we feel this place offers better views than Diamond Head.
On our way back to out hotel, we stopped by the Leonard’s Bakery food truck to snag some malasadas. You can’t go to Oahu without eating them!!!
We still had time to lounge poolside at the hotel before showering, packing up, and checking out. We just placed our luggage with the bell hop until it was time to head back to the airport.
Once we checked out, we explored Waikiki on foot and made friends with a couple of the Aloha Ambassadors who you’ll find all around the area. We chatted with them about island life, real estate, how tourism impacts the locals . . . and even love!
There was still so much time to kill so we hopped aboard the Waikiki Trolley, which ended up becoming a private tour! For whatever reason that day, we were the sole riders on the hour-long, round-trip route between Waikiki and Downtown Honolulu. We had such a great time with our driver, who indulged us with conversation about growing up on the island, all the changes he’s seen throughout the years, and just plain life. Seriously, the people here are sooooo nice and warm!
Our final hurrah was dining at House Without a Key, where we enjoyed a beautiful view and entertainment. I made sure to reserve ahead of time as I had read this was a very popular dining choice for Waikiki.
Finally, it was off to the airport to go back to our babies!