Time is the ultimate luxury. As my husband and I have moved into the middle act of our lives, we have found that spending more than one week in a single destination is invaluable. Time slows you down. It invites deeper exploration and creates room to reconnect.
We decided to gift ourselves the luxury of time when we traveled to Hawaii this past summer, opting to split our two weeks in paradise. The first week we spent on the island of Oahu with our two children and Grandma Sharon. The second week, Jason and I headed to the Big Island of Hawaii to reconnect and relax.
Week 1 Oahu Itinerary: Family Adventures And Iconic Experiences
Day 1 – Arrival In Oahu And Waikiki Check‑In
We arrived in the evening at the Hilton Grand Vacations Club Grand Waikikian Honolulu, checked in and let the day end quietly as we slipped into bed.
Day 2 – Resort Day In Waikiki And Casual Island Dining
In the morning, we prepared for the week ahead with a trip to Costco to stock up on supplies. With a full kitchen at our disposal and five people in our travel party, cooking in was essential. We then scoped out the Hilton Hawaiian Village Waikiki Beach Resort complex and walked from the hotel to dinner at Cheeseburger in Paradise. That evening, we stopped by Waikiki Brewing Company for a pint before heading to bed.
Day 3 – North Shore Oahu Food Trucks And Banzai Pipeline
Our family loves food and on this day, we headed to the town of Haleiwa to try Giovanni’s Shrimp Truck. It came highly recommended by another family we had met and it was a must-stop. It did not disappoint. The garlic shrimp was on point and the Hot and Spicy Shrimp had just the right amount of heat. We then made our way to the Banzai Pipeline to see if we could catch surfers riding the big waves. It was incredibly windy and there was not much surfing happening, but the golden sand stretched as far as the eye could see, creating the most beautiful backdrop for family photos.
Day 4 – Dole Pineapple Plantation And Local Coffee Stops
There is nothing more satisfying than pineapple soft serve and the very best can be found at the Dole Pineapple Plantation. This is a must-do for us every time we’re in Hawaii. The Green World Coffee Farm was recommended by a Plantation employee, so we stopped for macadamia nut lattes on the way back to the resort. With a line out the door, we knew it was going to be good the moment we pulled up.
Day 5 – Kualoa Ranch And “Jurassic Park” Filming Locations
On a whim, we decided it would be fun to see the area where “Jurassic Park” was filmed, so we headed to Kualoa Ranch for a four-hour tour. It turned out to be one of the highlights of our time on Oahu. Kualoa Ranch is a sprawling recreational haven where you can zipline, ride horses, take a catamaran, hop on an ATV, hike, bike or simply take in the breathtaking scenery. We opted for an open-air bus tour, which drove us through the ranch and highlighted several of the locations where the Steven Spielberg dinosaur classic was filmed.
Day 6: Day 6 – Resort Relaxation At Hilton Hawaiian Village
Our last day at the Hilton Grand Vacations Club Grand Waikikian Honoluluwas spent in a rented cabana after grabbing breakfast at Goofy Cafe & Dine. Watching fireworks over the lagoon was the perfect nightcap to this family vacation.
Day 7 – Inter-island Travel From Oahu To The Big Island
We waved goodbye to Grandma and the kids, and Jason and I took a quick interisland flight to the Big Island. After picking up our Jeep from the rental company, which is a must on the Big Island, we stopped at Costco and then headed to the Hilton Grand Vacations Club Ocean Tower Waikoloa Village.
Week 2 Big Island Itinerary: Nature-Focused Travel And Reconnection
Day 8 – Beach 69 Snorkeling And Lava Lava Beach Club
Jason and I set out to find Beach 69, also known as Waialea Bay Beach, for a morning of snorkeling. We stopped at Island Gourmet Markets first to pick up poke to go, then spent time in the water enjoying the sun and the views. That evening, we headed to Lava Lava Beach Club for an early dinner so we could watch the sunset from the resort.
Day 9 – Lagoon Day At Waikoloa Village
We spent the entire day on loungers at the Lagoon at Waikoloa Village. We got up early, which isn’t hard in Hawaii thanks to the time change, and watched the dolphins practice their moves. The rest of the day was dedicated to snorkeling and lounging. In the evening, we headed to Nui, an Italian restaurant at Ocean Tower, for pizza and Aperol spritzes.
Day 10 – Mauna Kea Sunrise And Coastal Hiking At Pu’uhonua O Honaunau
A bucket-list item for Jason and me was watching the sunrise from Mauna Kea, the highest point on the Big Island. At its peak, the mountain reaches 13,803 feet above sea level. Because there are advisories for taller individuals and those with blood pressure concerns, we chose to watch the sunrise from the visitor center, which sits at 9,200 feet. The drive and the view were absolutely breathtaking and made for a truly unforgettable experience. With a full day ahead, we then drove to Puʻuhonua o Hōnaunau National Historical Park to walk a section of the 1871 trail, where the coastal path offered sweeping and beautiful views of the ocean.
Day 11 – Kealakekua Bay Snorkeling At Captain Cook Monument
We took a boat tour to Kealakekua Bay, home to the Captain Cook Monument, so we could get in the water and snorkel. When you snorkel in this location, you are not allowed to set foot on the shore, which makes the experience feel more special. We had the best time with our tour operators and our boat had a water slide. On the way back, we stopped at several inlets and caves and spotted dolphins and a sea turtle. We wrapped up the day with dinner at Huggo’s on the Rocks, with a mai tai of course.
Day 12 – Pool Day And Resort Downtime
Pool, drink, food, repeat. This day was glorious.
Day 13 – Hawaii Volcanoes National Park And Kilauea
We had been closely watching volcanic activity and knew eruptions were happening about once a week. We decided to try our luck on the last day of our trip and Kīlauea did not disappoint. As we drove into the park, a red glow appeared in the distance and by the time we reached the crater’s rim, we were witnessing an active eruption. We spent hours walking the rim and standing in quiet disbelief, taking in one of the most awe-inspiring natural events we have ever experienced. We had to pry ourselves away and make the drive back from Hilo to the Kailua-Kona side of the island. This was truly our favorite part of the entire vacation.
Day 14 – Departure From The Big Island
Our two weeks had ended and it was time to head back to the mainland. We left already dreaming of where we’ll go next.
