Hawaii has been on our family bucket list for a few years, a siren call of beauty, nature, culture, history, city, country, cuisine, volcanoes, surfing, and the rest of it. This past summer, we got there. In the two weeks before Labor Day, my wife and I, and our two children, ages 15 and 11, visited Oahu, Hawaii (the “Big Island”), and Maui. As a visiting journalist, I was a guest, or I received a discount rate, for most of our accommodations and excursions, which allowed me to structure the trip as a kind of Hawaiian family sampler—five days in each of the three Islands, with stays at two properties on each island.
Knowing how our planning was helped by hearing the suggestions and experiences of others, I’ve tried to set down most of our positive experiences without being so detailed as to be burdensome. During our last swim in Hawaii, on the early evening before going home the next morning, we met another family from the New York City staying at the hotel, the Fairmont Kea Lani in Maui. After lots of friendly chit chat about life back home and highlights from our respective trips, it was very clear to me that, like New York, the islands of Hawaii offer so many points of interest and varied experiences that chances are a visiting family is not going to be able to see and do everything they want—but with a little planning it would be hard not to have a memorable trip. Hawaii is about 4,900 miles from NYC, or about 11 hours of flight time. I feel like I now have a pretty good idea of why it’s worth it.
The Itinerary: We had heard that the island of Kauai was a current hotspot for travelers, but after a lifetime of hearing about Oahu (i.e. Honolulu, Waikiki, and the North Shore), the Big Island, and Maui, we didn’t want to give those up, or cram in another island. We even had a sequence in mind: From the urban (Oahu), to the natural (the Big Island), to the luxurious (Maui). But those generalizations now seem overblown, for there wasn’t a day when we didn’t feel blessed with touches of natural beauty, good living, interesting experiences, and fun.
The Airline: Hawaiian Airlines offers the only non-stop flight between us and them, from JFK to Honolulu (on Oahu)—and one more important perk: The flight attendants were notably gracious, treating the passengers as if their vacation to Hawaii began the second they boarded the plane.
Special Resources: Perhaps the most helpful piece of advice I can offer for planning ahead, or for making choices while you’re there and is to use the Hawaii Revealed guidebooks by Andrew Doughty (hawaiirevealed.com) as one of your sources. For their mix of local savvy, deep research, and independent but fair-minded opinions, they are one of my favorite travel guides that I’ve ever used, at any age, in all of my wanderings. We used their guides extensively for each of three Islands we visited, and they also have one for Kauai. I was also greatly helped by the Hawaii Visitors and Convention Bureau (HVCB) with assistance from the island chapter bureaus on Oahu, Hawaii, the Big Island, and Maui. Visit their website, gohawaii.com, for all sorts of helpful info.
OAHU
Waikiki was like a smash up of Times Square, Madison Avenue, and South Beach—and it was the South Beach part that really wowed us. I don’t think any of us will forget the moment we entered our 18th floor suite at the Sheraton Waikiki, and shared a collective gasp upon seeing the terrace views of the expansive emerald ocean and the Diamond Head volcano. It was a jolt of giddy anticipation, like we had come this far for really good reasons. The next day we visited the major memorials at Pearl Harbor. I was not prepared, but am forever thankful, for how much I learned and how deeply I was moved, especially at the USS Arizona Memorial, which floats calmly and reverently over the remains of the Arizona itself. Practical tip: If you don’t get a ticket in advance to see the memorials at Pearl Harbor, there’s all sorts of private tours you can spend a lot of money on. Or, like us, if you get there early (we arrived at 7am), you should be able to score some of the hundreds of free tickets they give out every day, and then use the self-guided audio tour, which is very good.
Our other big excursion was a day trip up the east side of Oahu, with key stops for rock formations (La‘ie Point), shrimp trucks (Gionvanni’s), and corn stands (Uncle Woody’s) before making our way over to the heart of the North Shore and Sunset Beach. A famed surfer haven in winter, the water was gentle, pristine, and uncrowded. Or in other words, perfect. On a rainy day, we visited the ‘Iolani Palace, which was the home of Hawaii’s last king, David Kalākaua. It’s a wonderfully restored historical and cultural time-capsule, a reservoir of native pride infused with the tragic undercurrent of how Hawaii first came under the control of a few unscrupulous American businessmen following the King’s death. If you want to understand more about American history, you visit Pearl Harbor. If you want to understand more about Hawaiian history, you visit ‘Iolani Palace. And because we visited the ‘Iolani palace, we also made another pleasant discovery: In pursuit of a mid-afternoon lunch, we happened upon a few downtown blocks around Bethel Street and Nuuanu Avenue percolating with a savvy urban vibe, thanks to their shopping boutiques and bars. We loved a shop called Island Keepsakes.
Accommodations: 1. The Sheraton Waikiki is big, bustling, and well run, with an infinity pool that looks out to the ocean. I especially recommend paying a bit extra for access to the Leahi Lounge, on the 30th floor, where you can grab a quick breakfast, or retire to later in the day for all sorts of yummies, while enjoying views that are even more transcendent that the ones from your room. Another good reason to stay at Waikiki is that the tides are relatively mild, easy to swim, and a good place for surfing lessons for beginners. 2. The Royal Hawaiian, with its many faceted hues of pink and red, is one of the crown jewels of Starwood’s Luxury Collection Resorts. Waikiki’s second oldest hotel, it was renovated a few years ago in a manner that maintains its classic beauty while outfitting it with all the modern amenities. The place was so pretty that I spent a few pockets of free time walking around the property (indoors and out) and just to admire it.
Favorite Meal: Dinner at the Ocean House Restaurant at the Outrigger Reef Waikiki Beach Resort.
If We Had To Do It Again: I’d visit the Polynesian Culture Center, for a deeper dive in the Hawaiian and Polynesian history and culture, and to see their acclaimed luau; I’d also plan for more time at Shark’s Cove and Turtle Beach, two amazing spots on the North Shore.
HAWAII—THE “BIG ISLAND”
The Big Island is not only larger than all the other Hawaiian Islands combined, its topography is incredibly diverse: Stark volcanic planes, lush tropical valleys and waterfalls, and some of the prettiest beaches on the planet—not to mention a rugged swatch of green pastures that is Hawaii’s version of cowboy territory. Who knew? The centerpiece experience was our hiking and driving around Hawai’i Volcanoes National Park, where the main event there was the Kilauea Iki Trail, a gentle descent through a rain forest to the immense floor of the crater, which looks like a big bowl of grey and scrappy moonscape. For my wife, the crater was most special experience of the trip (I’ll share my vote later).
The remaining days brought other fun. At Skyline Adventure’s seven-line zip course, the family beginners (my wife and I) were expertly nurtured on the minor runs until we were ready for the grand finale: A soaring minute-and-a-half run, 450 feet in the air over a waterfall. On that same day, in which we were traveling from our first accommodations (Kipuka Cottage) near Volcanoes National Park, to our next one (Hapuna Beach Prince Hotel), on the other side of the island in Kohala, we have a few other notable diversions. The Waipi’o Valley, a place of great historical importance, is only accessible through a road with a 25-degree slope, which is all but prohibitive except if you use one of the local tour services (and their 4-wheel drives, or capable mules). We didn’t have the time to do it, but the overlook was so breathtakingly impressive, and the history so interesting to contemplate, I still wanted to give it a shout out.
We then traveled at dusk across Waimea, the rugged old cowboy country I had alluded to. Once settled in on the west coast, we had a bunch of water fun. We loved snorkeling in the Kohala Coast waters with Captain Steve of Kohala Sail & Sea, which specializes in taking smalls groups (up to six passengers) on sunset cruises, and humpback whale watching, as well as snorkeling, on his dandy 34-ft sloop. And as we were staying right there, we spent a lot of time at Hapuna Beach, which is widely and deservedly recognized as one of the most amazing beaches in the world. There was on-land adventures too, of course. We are still enjoying some of the goodies we bought during our visit to the Hamakua Macadamia Nut Visitor Center in Kawaihae, which offers free factory tours. And when we drove south to see Kailua and Kona, the big highlight was the Pu’uhonua o Honaunau National Historical Park. To ancient Hawaiians it was “a place of refuge,” where lawbreakers, if they could arrive there without first being killed, could essentially have their sentences commuted—like the ultimate get out of jail card. Near the water, its restored homes, temples, stone walls, and grounds, do have the feel of a place important and apart—and it was nice to be there and contemplate their bygone world.
Accommodations: 1. Working with a friend who is a master carpenter, a travel journalist named Bill Harby built his dream home, Kipuka Cottage, in the woods about 12 miles from Hawai’i Volcanoes National Park. They knew what they were doing. The split-level cottage is framed by a very pleasing geometric patterns (see the photos), incorporating lovely woods and big windows. We found it to be the perfect respite from everything, including more formal lodging. 2. The Hapuna Beach Prince Hotel sits like a big luxurious starship with its multi-layers of lounging and shopping and eating embracing the beach with open arms. Among its amenities is a noted golf course, but our time there was all about the pool and the beach.
Favorite Meal: A three-way tie for the dinner at three very different places: Volcano House Hotel (fine dining looking out on the flames of the active volcano); Merriman’s Waimea (fine and fancy dining); and the Blue Dragon (crazy cool outdoor restaurant and bar).
If We Had To Do It Again: More time for the sights and experiences in Kona.
MAUI
Visitors to Maui always discuss whether they plan to take the Road to Hana, an epically beautiful and winding journey to the east side of Maui. Thinking that it would just chew up too much of our time and energy, we opted for Plan B: The Road to Lots of Other Cool Places, including the town of Makawao (a neat mix of cowboy roots and artsy boutiques); the Nakalele Blowhole (much like it sounds); the neat beach town of Pa’ia, and then my favorite experience of the trip: Watching the surfers at dusk at Ho’okipa Beach Park, with the bonus of quite a few outsized turtles resting on the shore. Another drive, between our first hotel (Kāʻanapali Ocean Resort Villas) and the second (the Fairmont Kea Lani in Wailea) allowed for a long pit-stop in the town of Lahaina, noted for its mix of art galleries, shopping boutiques, eateries, and a very large banyan tree.
On Maui, we also took our second snorkeling trip, this time with a big boat (accommodating about 50 passengers) called Trilogy, on a well-run trip to the waters near Molokini Island, in which the kids learned how to snuba—a gentle hybrid of snorkeling and scuba. The same day we also visited the terrific Maui Ocean Center, where I recommend the behind-the-scenes store for a deeper dive into how the aquarium works and marine education. One night on Maui, we attended our first luau, a dinner show called Drums of the Pacific at the Hyatt Regency Maui. It was a schmaltz fest of impressive hips and fire twirling, but I did love when but both of my children joined the other brave tourists on stage for the requisite bit where the performers try to teach the mainlanders how to sway, and the mainlanders enjoy stumbling about.
Accommodations: 1. For families, the Kāʻanapali Ocean Resort Villas is an especially, vibrant, and kid-centric resort, with suites for all, and well-designed multi-use central pool areas that are a hub of activity both day and night. It’s what good time-shares should be, but it also offers regular vacation options as well. 2. The Fairmont Kea Lani, Maui is grand and gorgeous, and yet quiet and easygoing. Maybe it was because it was the end of the trip and we were feeling sentimental, but the hotel felt like the right blend of everything we like in an upscale hotel. Plus they get a special citation for having our favorite breakfast buffet.
Favorite Meal: A two-way tie between dinner at the Fairmont’s Kō (incredible Asian and Hawaiian fusion), and Mama’s Fish House (a deserving legend).
If We Had To Do It Again: We’d drive the Road to Hana, of course. But we would plan our itinerary to make sure, after the long drive, that we stayed on the east coast for a night or two before take the Road back again.
Eric Messinger is the editor of New York Family.
