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.
FASHIONABLE FUN LOVER’S ITINERARY
Start in Waikiki and perhaps return here for your final two 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.
POLYNESIAN PURIST’S ITINERARY
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.
JADED ROMANTIC’S ITINERARY
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 another four or five 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.
NATIONAL PARK NATURALIST’S ITINERARY
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.
BUILDING BLOCKS FOR PERFECT DAYS IN PARADISE
These regional, hour-by-hour planners will get you started on how best to dip into the islands. But a word of caution: If you try to do everything mentioned in the time allotted, you might not feel like you’re on a vacation. Use them merely as a guide.