fbpx Skip to main content

Hawaii Itinerary

How long was your stay?

9 days

How did you travel?

As a couple

Tell us why you traveled to this destination.

My partner and I have friends that recently moved to Honolulu, so we knew we had to visit! We went to Maui a few years ago and were excited to explore another Hawaiian Island together.

Give us all the details! Tell us where you went and what you did on your trip.

DAY ONE: We arrived at the Honolulu Airport late afternoon and we were HUNGRY so we headed to the International Market Place in Waikiki and grabbed a bite to eat at Shore Fyre. I’ll always recommend kalua pork or fresh poke when in Hawaii! We then headed to our house, unpacked, and headed to Queen’s Beach to catch the sunset before calling it a night.

DAY TWO: Our first full day in Hawaii started with a hike at Diamond Head State Monument. This is a family-friendly hike that leads you through a former fort and to the summit of a volcanic crater with incredible views! We then grabbed an acai bowl at da Cove Health Bar and Cafe and headed back home to rinse off and change for a beach day at Kahala Beach Park. Want to swim with a dolphin? The Kahala Hotel & Resort has a pool where you can do just that! To end the night, we ate dinner at the house and then headed to Hawaiian Brians Social Club for drinks, games, and live music. So much fun!

DAY THREE: Our travel dates happened to crossover with Superbowl Sunday, so we took a stroll around downtown Waikiki and grabbed a cocktail at Tiki’s Grill and Bar before grilling at the house for the big game and hanging out with friends for the night.

DAY FOUR: Not only did we get to watch the Superbowl in Hawaii, but we also celebrated Valentine’s Day here! Our morning was spent at the Pearl Harbor National Memorial, where we toured the USS Missouri Battleship.

A great experience for all ages. We then drove around the University of Hawaii campus and grabbed lunch at Off the Hook Poke Market. It’s a little hole in the wall and SO GOOD. We then headed to Sandy Beach on the South Shore of Oʻahu. To end the night, we had dinner at Hula Grill Waikiki, took a walk along the beach, and then had dessert at Buho Cocina y Cantina. We had to get the Gordito Special!

DAY FIVE: After eating our body weight in ice cream and churros the night before, we knew we wanted to get our bodies moving for day five so we headed to the Koko Crater Railway Trailhead. This is a 1.6-mile out-and-back trail on an abandoned railroad. It’s a great challenge with even greater views!

For lunch, we stopped at Fatboy’s for chicken katsu and mac salad. A Hawaiian classic! We then headed home to shower and relax before grabbing dinner at Maui Brewing Company and window shopping in downtown Waikiki. To top it all off, we finished with another sunset at the beach.

DAY SIX: We grabbed smoothie bowls at Bogarts Cafe for breakfast and then headed out for our sea turtle excursion with Living Ocean Tours. Not only did we get to snorkel with sea turtles, but we were also lucky enough to see a pod of dolphins while on the boat! Back on shore, we grabbed a snack and coffee from The Gallery Waikiki and did a light hike to Manoa Falls Trail. Back to the house for the night!

DAY SEVEN: Our wake-up call on day seven was early as we headed to the North Shore for a 9AM excursion to cage dive with sharks! The company we booked with is called North Shore Shark Adventures and it was awesome! We had a casual lunch at the Haleiwa food trucks and then took a drive up to the Banzai Pipeline to watch the locals surf some massive waves. We then headed to Waimea Valley which has a waterfall you can swim in at the end of the trail. So pretty! We snorkeled for an hour at Sharks Cove before heading back to Haleiwa to check out the beach shops before driving home. Dinner at the house after a long day!

DAY EIGHT: We grabbed a breakfast burrito at Kono’s Northshore and then headed to the Honolulu Zoo for the day. For happy hour, we went to Sky Waikiki. This bar is on the rooftop of a 19-story building and the views are stunning! We then had dinner at Momosan Waikiki for some of the best ramen I’ve ever had. One more stroll downtown for our last night!

DAY NINE: Our last day on O’ahu started early as we drove to Kailua on the east shore where we did the Lanikai Pillbox Hike to catch the sunrise. So worth it! We grabbed a coffee from Coffee Talk and had to get in one last round of poke from Ono Poke. Seriously SO GOOD. Then it was back home to the states. Aloha!

Would you recommend this trip to a friend?


What was the highlight of your trip?

Hiking up Koko Head was physically challenging but so much fun and definitely a highlight. It was truly breathtaking – both the hike AND the view! I also loved stepping out of my comfort zone and cage diving with sharks. There was an adrenaline rush at first, but the experience became somewhat calming once I realized how safe I was.

If you were to take this trip again, is there anything you would add or do differently?

I wish we had planned more snorkeling trips, they’re so fun!

Sydney & Tyler

Travel itineraries are an essential part of MyPinerary. By sharing the details of your own travel experiences you are helping other travelers plan their perfect trip. Become part of the MyPinerary community by submitting your travel itineraries.