Family Trip to Hawai’i

After months of research, we knew we wanted to explore the bustling city life in Honolulu and have some down time enjoying the relaxing culture of Maui. After a long flight from Chicago, we touched down in paradise.

A room with a view

Honolulu

First, we stayed in the heart of downtown Honolulu at The Laylow, Autograph Collection. We knew we wanted a central location where we could walk to various restaurants, coffee shops, and shopping, but we didn’t need to be right on the beach in Waikiki because we knew we had plenty of beach time ahead. While staying in Honolulu, we wanted to take advantage of the many things the city had to offer.

We walked to dinner at House Without A Key at the incredible Halekulani Hotel. We were treated to a delicious dinner, a beautiful ocean view, and live music complete with a hula dancer.

The Old Lahaina Lu'au: a trip highlight

Around O’ahu

One of our favorite stops in O’ahu was at Leonard’s Bakery, where we sampled several of their malassadas (Portuguese donuts). Another highlight of staying downtown was being within walking distance to Kona Coffee Purveyors and enjoying their authentic Hawaiian coffee.

An O’ahu sunset

After spending a few nights downtown and exploring the eastern (or windward) side of O’ahu, we headed to the leeward side (the west) of the island and checked into Aulani, A Disney Resort and Spa. While at Aulani, we enjoyed time at the various pools, racing down the waterslides, and swimming in the most beautiful ocean water we’d ever seen thanks to the man-made lagoons in Ko Olina.

During our stay at Aulani, we made time to visit Pearl Harbor and drove up to the North Shore of the island for some shopping and swimming at a waterfall.

Swimming at Waimea Falls

Maui

After our time on O'ahu, we took a short flight to the island of Maui. We stayed at the Fairmont Kea Lani, where we were greeted with fresh flower leis and treated to an amazing ocean view from our large, recently renovated hotel room.

During our time at the resort, we spent most of our days enjoying the swimming pool. The kids had fun making friends and utilizing the water slide.

Adult pool at Fairmont Kea Lani

Family pool at Fairmont Kea Lani

Because the Fairmont is located on a stretch of beach near many other luxury resorts, we took an evening walk over to check out some of the other resorts and enjoyed dinner at Spago at the Four Seasons Maui.

Takeaway

Hawai’i is a great destination for people of all ages. A must-visit destination if you enjoy beaches, welcoming people, great weather, delicious food, and of course, pineapples!

Shave ice is a popular treat you can enjoy all over Hawai’i. My family enjoyed trying samples from multiple locations, but our favorite was Island Girl Shave Ice, a truck parked on the side of the road. Don’t hesitate to try any food trucks you might come across!

For more inspiration and insider recommendations, visit our Hawai’i page.