If you can afford the splurge, rent a bright, shiny convertible -- the perfect car for Oahu, since you can tan as you go -- and head for the North Shore and Hawaii's surf city: Haleiwa, a quaint turn-of-the-20th-century sugar-plantation town designated a historic site. A collection of faded clapboard stores with a picturesque harbor, Haleiwa has evolved into a surfer outpost and major roadside attraction with art galleries, restaurants, and shops that sell hand-decorated clothing, jewelry, and sports gear.
But getting to the North Shore is half the fun. You have two choices: The first is to meander north along the lush Windward Coast, through country hamlets with roadside stands selling mangoes, bright tropical pareus, fresh corn, and pond-raised prawns.
The second choice is to cruise up the H-2 through Oahu's broad and fertile central valley, past Pearl Harbor and the Schofield Barracks of From Here to Eternity fame, and on through the red-earthed heart of the island, where pineapple and sugar-cane fields stretch from the Koolau to the Waianae mountains, until the sea reappears on the horizon. If you take this route, the tough part is getting on and off the H-1 freeway from Waikiki, which is done by way of convoluted routing on neighborhood streets. Try McCully Street off Ala Wai Boulevard, which is always crowded but usually the most direct route.
Once you're on H-1, stay to the right side; the freeway tends to divide abruptly. Keep following the signs for the H-1 (it separates off to Hwy. 78 at the airport and reunites later on; either way will get you there), then the H-1/H-2. Leave the H-1 where the two "interstates" divide; take the H-2 up the middle of the island, heading north and following signs directing you toward the town of Wahiawa.
The H-2 runs out and becomes a two-lane country road about 18 miles outside downtown Honolulu, near Schofield Barracks. The highway becomes Kamehameha Highway (Hwy. 99 and later Hwy. 83) at Wahiawa. Just past Wahiawa, about a half-hour out of Honolulu, the Dole Pineapple Plantation, 64-1550 Kamehameha Hwy. (tel. 808/621-8408; www.dole-plantation.com; bus no. 52), offers a rest stop with pineapples, pineapple history, pineapple trinkets, and pineapple juice, open daily from 9:30am to 5pm. This agricultural exhibit/retail area also features a maze kids will love to wander through, open daily from 9am to 5pm; admission is free. However there are fees for the tours: the Pineapple Express is a single-engine diesel locomotive with four cars that takes a 22-minute tour around 2 1/4 miles of the plantation's grounds, with an educational spiel on the legacy of the pineapple and agriculture in Hawaii. The first tour departs at 9:30am, and the last tour gets back to the station at 5pm. Cost is $8 for adults, $6 for children 4 to 12 (free for ages 3 and under). The Plantation Garden tour is a self-guided tour through the various crops that have been grown on Oahu's North Shore. The tour costs $5 for adults and $4.25 for children. The Maze Garden Tour is $6 for adults and $4 for children ages 4 to 12, free for children under 4 years old. "Kam" Highway, as everyone calls it, will be your road for most of the rest of the trip to Haleiwa.
On the central plains of Oahu, tract homes and malls with factory-outlet stores are now spreading across abandoned sugar cane fields, where sandalwood forests used to stand at the foot of Mount Kaala, the mighty summit of Oahu. Hawaiian chiefs once sent commoners into the thick sandalwood forests to cut down trees, which were then sold to China traders for small fortunes. The scantily clad natives caught cold in the cool uplands, and many died.
Also on these plains, in 1908, the U.S. Army pitched a tent that later become a fort. And on December 7, 1941, Japanese pilots came screaming through Kolekole Pass to shoot up the Art Deco barracks at Schofield, sending soldiers running for cover, and then flew on to sink ships at Pearl Harbor.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.