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Photo by Samantha Sophia
  • By Kim Grant

To help in your voyage of discovery, each Hawaiian island will have recommendations for Musts for First-Time Visitors and Ideas for Repeat Visitors and A Perfect Day in… I trust you’ll use these as a jumping-off point of departure.

Constructing an itinerary for Hawai‘i is mainly a matter of deciding how many islands to visit. On any single island, select one spot and use it as a base for sightseeing. On Maui and the Big Island, you might want to move once or twice to get a better sense of their diversity, and some special-interest travelers — say, golfers — may want to sample more than one resort. But point-to-point travel is not necessary or generally desirable on an individual island.

I have two rules for Hawaiian itineraries: Visit at least two islands on any trip, and spend a minimum of five days on an island. The rules are clearly contradictory if you have less than 10 days, in which case I’d suggest extending your trip. You also need to anticipate a couple of days of low-energy jet lag on arrival. Depending on where you are starting and the time of year, Hawai‘i is two to six time zones away.

When you can arrange only a week and it’s your first trip to Hawai‘i, forget the 5-day rule and visit two islands. The islands are so different from one another and have so much to offer individually that it’s important to experience some of the variety. A person who has been to one island and claims to have seen Hawai‘i is like a New Yorker who has been to Los Angeles and claims to know the West.

If this is a return visit to the islands and you’ve gone beyond Waikiki and West Maui, a catalog of exceptions comes into play. Use Honolulu for a short stopover of less than 5 days on the way to another destination. Or pick a favorite spot on one island and sink into the sand for an extended stay. Or consider a 2- or 3-day jaunt to Moloka‘i or Lana‘i or a remote hamlet such as Hana for a change of pace. Once you have some acquaintance with at least O‘ahu, Maui, Kaua‘i, and the Big Island, these two itinerary rules become almost infinitely flexible.

Novices should be more cautious about breaking the two rules. They should design an itinerary with the two principles in mind and build it around their personal interests and the amount of time they have.

I’ve taken four prototypical personality types common among Hawai‘i visitors and built an itinerary for each. Few of you are exclusively one of these types, but if you feel a particular kinship with one, the itinerary should work well for you.


Start in Waikiki and perhaps return here for your final 2 days. Waikiki remains America’s most famous beach and offers more options for entertainment and nightlife than all the neighbor islands combined. The second stop is West Maui, at or near either the Ka‘anapali or Wailea resorts. Ka‘anapali is more active, while Wailea is more sensitively planned. The final destination is Kaua‘i, which shows start-and-stop signs of displacing Maui as the choice of the chic. Split your days almost equally among the three islands, with some possible fluctuation between O‘ahu and Kaua‘i depending on whether you are a traditionalist or riding a new wave.


Catch a flight to the Big Island. You may have to change planes in Honolulu, but don’t leave the airport. Spend most of your two weeks on the Big Island. The best time to come is early April, during Hilo’s Merrie Monarch Festival. If you can arrange this, use Hilo as a base for exploring the southern half of the island. In other periods, South Kona, Volcano, or Kailua-Kona may be a better headquarters. But concentrate your visit in the north, in the Kohala region. Don’t miss the Pu‘ukohola and Mo‘okini heiaus, the Waipio Valley, the petroglyph fields and ancient fishponds of the Waikoloa and Mauna Lani resorts, and the Pu‘uhonua O Honaunau National Historical Park. Near the end of your trip, fly to Moloka‘i for a few days of native-style relaxation.


If you’re difficult to impress but can be stirred to passion by the authentically poetic, you should seek out some of Hawai‘i ’s most idyllic hideaways. Hana is an imperative for one-third of your time. You might want to remain on Maui for another 4 or 5 days in Makena, Kapalua, or Napili, or perhaps substitute a similar amount of time on the North Shore of Kaua‘i. In winter, I would stick with Maui; in summer I’d elect Kaua‘i. My third destination would include the South Kohala resorts of the Big Island. A well-off jaded romantic could not do better than dividing the days among these spots.


Your focus is Haleakala National Park on Maui, Hawai‘i Volcanoes National Park on the Big Island, and the north coast of Kaua‘i. On Maui, stay on the eastern half of the island, probably Upcountry, and make the drive to Hana one day. On the Big Island, choose lodging in Volcano Village. Kaua‘i offers a range of accommodations moderately convenient to its natural splendors. I would opt for somewhere around Hanalei, probably Princeville, though the Kapa‘a area is midway between the dramatic scenery of the North Shore and the South Shore’s Waimea Canyon.


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