Multigenerational travel is becoming more and more popular…and with good reason.  It’s a chance for kids, parents and grandparents to relax and enjoy each other’s company in new and fun settings. Away from the dishes, the trash that needs to be taken out and that room that needs to be cleaned, all generations can do what they like and create new memories.

Oahu sunset in Hawaii


What about Hawaii?

So where would you go if you had two weeks with the whole clan? How about Hawaii?  As America’s 50th state, it’s one that most American’s have never visited. That’s a shame, as it is arguably one of the most interesting and beautiful of all. So let’s imagine a two-week itinerary and see how this sounds.

Checking with Kayak, I found fares are almost half the cost if you fly into Oahu as opposed to flying directly to the big island or Maui. Once you arrive in Oahu, which you’ll want to see anyhow, you can fly or sail to the other islands very inexpensively.

Plane fares

Before you make reservations, check the media and festival guide available on the Oahu website, as there’s nothing worse than missing a big event by a day or two when you could have planned otherwise. It might be a movie fest, fireworks, book fest or a music event – there are things for all interests.

When thinking of accommodations, there are all sorts of possibilities as well. Consider renting a home instead of staying at a hotel.  Checking on (Vacation Rentals By Owner) I see a 3 bedroom, 3 bath, sleeps 10 home with views of the ocean and Diamond Head for as little as $390 per night. At $39 per person per night, you’d pay that much at the local hostel.


Hawaii is not an inexpensive destination, and cooking a few of your own meals (especially breakfast) could save hundreds of dollars. Usually kids are happy with cereal, so save your money for other more expensive attractions later in the day.

Renting a car is also something to consider. If you are happy to spend all day, every day at the same beach, forget it; but if you’d like to take in the sights, a car is a definite advantage. I can’t stay still, so I’m off and exploring after one day at the beach. Here would be my bucket list while on the isle of Oahu:

Waikiki Beach You haven’t been to Hawaii if you don’t spend some time on Waikiki Beach.  Make sure to get Diamond Head in the background when you are taking your ‘selfies’. Thousands of shops and restaurants line Kalakaua Avenue, just beyond the beach, so you’ll never be far from food and sustenance. Some hotels lining the beach have patios where it’s great to have dinner and drinks and watch the sun go down.

Waikiki Beach

Good places to hang out would include the Hilton Hawaiian Village Beach Resort (whether you stay there or not). I’ve stayed here four times and loved it each time. The Atlantis submarine departs from here if you want a “down-under” view of Hawaii.

A mile or two from Waikiki is Aloha Tower Marketplace which is where most of the other boat tours start.  You can go whale watching, snorkeling, take a cultural cruise or a dinner cruise from here on the Starlet.

Aloha Tower Marketplace

Pearl Harbor is a must. The pre-tour videos and narration are well done and the visit to the floating memorial above the USS Arizona is quite moving.

Pearl Harbor view from helicopter

Heading across the island, you’ll find the Dole Plantation.  Fun stop for kids with a twenty minute train ride through the plantation. My biggest disappointment in Hawaii was buying a small tub of pineapple pieces from their gift shop and finding that they had been doused with preservatives.

Drive all the way to the northwest corner of the island if you want to see big waves.  The North Shore is famous for the surf and this is where most of the surfing competitions take place.  Biggest surf is typically in the winter however.

Polynesian statues

Follow the ocean highway to the southeast tip of the island and you’ll pass Kaneohe Bay, lighthouses, Asian temples, blowholes, and finally arrive at Diamond Head.  Go ahead and hike the path to the top. Anyone can do it. I followed a little Japanese teenager in stiletto heels, so I sure wasn’t complaining in my tennis shoes. The view from the top is beautiful.

View from Diamond Head

I’d allow five or six full days to enjoy Oahu and then catch a boat or plane to Maui. Maui has twice the natural beauty of Oahu and is nowhere near as touristy. Resorts and condo’s line Maui’s western shore with beautiful views of the sunset, but you’ll find much cheaper accommodations further east along the north shore.


Continue reading about Maui by clicking here.

Also published on Medium.