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In 2021 my family decided to take a once-in-a-lifetime holiday trip to Hawaii, and we had a total of 16 family members. Folks ended up in 3 different hotels on Oahu / Waikiki based on who has points at what hotel or timeshare; we stayed in the Grand Waikikian.  Hilton has several hotels, pools, restaurants, shops, and lagoon in a ‘Village’ so that was handy albeit a bit crowded at times. We never did figure out where the Uber pickup was located.

Tip: If you are traveling to Hawaii in COVID-era, try to get a wristband at your departure gate (they pre-screen your vaccine cards) before you board the plane. Then you can skip the hour-long line to get verified after you land. Somehow we didn’t see that out bound but we did see after we returned.

I wanted to arrive a few days early to explore with my sweetie, since I knew once family arrived it would be harder to break away. The main excursions I planned were day-trips to 2 well-known beautiful beaches, and a helicopter tour around the island. So those are the primary content in this blog, plus a bike ride and some great restaurants.

Helicopter Tour around Oahu Island

The tour was meant to be a surprise for my boyfriend, and it was just the two of us. Once we arrived I had to do some arm twisting but he agreed to board the door-free helicopter ride adventure. My logic on safety was that this is a professional company, all they do is helicopter touring and flying, and those straps are engineered to keep people from falling out of an open helicopter. Plus the views would be so much better without that pesky door in the way. Greg didn’t complain but his hand was latched firmly to the handle-strap from start to finish. I booked with Magnum Helicopters, and i was able to book it (and get discount) through my Hilton Grand Vacation timeshare concierge in advance (thanks, Rachel!) There are other helicopter tour companies as well. I chose Magnum due to high ratings, and they film TV footage for the Magnum PI television show which was a cool addition to the experience. 

Tip: When choosing a high-risk excursion like helicopter rides, sky diving, bungee jumping, speed boating, etc. make sure you book the most professional outfit that you can find. Pay the higher rate here, and reserve your coupon-cutting for a low risk activity, like a cheap lunch or taking the bus instead of renting a car. Stay away from parasailing with a company that sends a sales person with brochures to solicit sunbathers on the beach, as a rule; book a reputable company through your hotel concierge instead. 

When I went to research the flight in advance, I was disappointed they had a weight limit for the front seat, which we did not satisfy. Once we got there I realized why – the aircraft is actually very tiny! In the front was our slim pilot (left), an adult man (right) and his pre-teen daughter (center) who barely fit. I was behind the pilot and my sweetie was behind the passenger. In between us was a structural bulkhead so really we were packed in pretty tight. They don’t allow you to hold a phone / camera / purse, which became clear later why. I really wanted video so they let us work around this two ways. One, for a nominal fee we bought their plastic case that you can put a flat phone in, which Greg used. I had my GoPro Hero in a sealed case with strap, and they allowed it around my neck and changed out my strap for one more secure. So the videos are from my go-pro and a bit jiggly. You can also buy their video but I really wanted the home-made video since it more accurately represented my personal experience.

Now to the good part. The views were stunning!!! We departed from Honolulu airport and flew a counter clockwise path around the island, mostly from above the beach. I was on the left (port-side) so saw more of the mountains and plains; Greg (starboard-side) saw more azure blue waters, although the pilot turned here and there so we could all see everything. To me this was an ultimate way to see the beauty of the Oahu island in a short time. We saw beaches, mountains, plains, pineapple plantations, wind farms, solar farms, cattle and crop farms, and flew directly over battleships and aircraft carriers in Pearl Harbor  

Note: This type of excursion is not for everyone.  In addition to generally getting into an aircraft with no door and strapped in by just a seat belt… it’s quite loud, and lots of vibration and wind and noise even with the headset they provide. The helicopter blades, whirling and keeping the aircraft up, also push the air down. With no doors, that wind comes into the helicopter and you really feel it the whole time. When we lifted off I thought, no way we will be doing this for an hour. 

In total it was about a hour from lift off to touch down. It was amazing, and I’m happy to share with my readers so you can enjoy the story and views from the comfort of your computer or handheld device.

Click HERE to watch the short (5-minute) video compilation

Click HERE to watch the long (15-minute) video compilation

Kailua Beach

Once family arrived we took two day-trip beach excursions. I try to avoid car rental on travel when possible as it’s expensive, time consuming, and a hassle to manage so I had done some research in advance. The first was a bus trip across the island from Honolulu to Kailua beach. Greg and I took this with my brother Mark and his sweetie. I had scoped it in advance and it was an inexpensive alternative to renting a car. Although we did walk a bit (about half mile on each end) we only paid about ten dollars per person and the beach was gorgeous.

Tip: When visiting with a large group of friends or family, I like to set aside a little time to spend with each person or with smaller groups so that we get some quality time. It takes some effort but then we get to connect and catch up in a more intimate setting. It’s hard to get that kind of connection at the big dinner table.  

Besides watching someone on the beach make several attempts at kite sailing, there wasn’t a lot of noisy/busy activity and most everyone was just relaxing and enjoying the water and sand. Palm trees line the sand/grass border so you can choose how much sun or shade you want. and mountains in 3 directions provide a lovely backdrop. There is a building with toilets and showers for changing and cleaning up and no fee to use the beach.

Hanauma Bay 

The other beach day trip was to Hanauma Bay which is a famous snorkeling site with beautiful beach. It’s quite a bit closer to Honolulu but still requires either a car or an Uber (roughly 100 USD round trip). Yet this was so worth it! My sister Deb and her sweetie were with us and I had to do some arm twisting again, but in the end she was so happy that they came. You pay a nominal fee to enter, they give you video about the history and how to protect the bay, then you walk or ride down a long ramp to approach the beach. Apparently in recent past they allowed too many visitors which damaged the area, and is more restrictive now to protect and regrow the natural life.

Tip: Pre-book your reservation day and time to Hanauma Bay online a few days prior to the trip. You still have to pay when you arrive but if you don’t have a pre-booked time slot, there is a risk you will be turned away.

This beach you can rent snorkeling gear, although I brought mine. In the water there are numerous schools of fish especially over shallow rocky areas. When snorkeling on a busy beach, generally its best to aim for clear water and fewer people, and this proved successful on our Hanauma Bay trip. There is a building with toilets and showers for changing and cleaning up. There are also outdoor showers, but don’t use soap/shampoo as it goes directly into the ocean. The beach, the water, underwater, and the approaching ramp all provide gorgeous views. This is a must if you visit Honolulu.

Click HERE for Snorkeling video

Bike Ride & Great Meals 

Later in the week, Greg and I picked up bike rentals and rode around Honolulu, through Kapahulu park, and to the base of Diamond Head. Although affordable we had some small challenges with the Biki bike app. More than once the bicycle in the kiosk wouldn’t recognize the digital code and we saw others with this problem. Hopefully it will be fixed by the time you visit.

Tip for foodies: Check out our two favorite restaurants: First, Tane Vegan Izakaya- the sushi was so creative, beautiful, and delicious that you don’t need to be vegetarian to really enjoy the food. Also, we enjoyed Chef Chai – a bright modern Asian fusion restaurant with spectacular meal experience for a table of 8. 

The rest of the trip was family-oriented so I won’t share since you would have a different experience. It was helpful to have family in the same hotel, usually. But I will say that next time I have a large family gathering, I would choose a place either closer to home or less expensive or both. Coordinating 16 people to get together for meals and holiday activities requires quite a bit of organizing and that takes away from time spent, say, lounging on the beach.  

Aloha!