The smallest of all the Hawaiian Islands, Lanai was once a big pineapple plantation and is now home to two exclusive resorts, hundreds of years of history, and just one small town with some of the friendliest people you will ever meet. Like the island of Molokai, there are no direct flights from the mainland to Lanai. You will have to fly into Honolulu and then take a commuter plane to Lanai.
Day 1: Arriving & Seeing Hulopoe Bay
After you settle into your hotel, head for the best beach on the island: the marine preserve at Hulopoe Bay. It's generally safe for swimming, the snorkeling is terrific, and the fish are so friendly you practically have to shoo them away.
Day 2: Touring the Island in a Four-Wheel-Drive Vehicle
Lanai is a fantastic place to go four-wheeling. Generally, you won't need a car if you're staying at one of the two resorts or at the Hotel Lanai (they provide shuttle service), so splurge and rent a four-wheel-drive vehicle for 2 or 3 days. Get a picnic lunch from Pele's Other Garden and head out of Lanai City to the Kanepuu Preserve, a 590-acre dry-land forest. Next stop is Garden of the Gods and a picnic lunch at Polihua Beach, Lanai's largest white-sand beach. The beach generally is not safe for swimming and can be windy, but it will probably be deserted and you'll have a great view of Molokai in the distance. After lunch, reverse direction and head to Shipwreck Beach and then on to Keomoku Village.
Day 3: Spending a Day at the Beach
Plan a lazy day at Hulopoe Beach. Grab a book, watch the kids play in the surf, or take a long walk around the crescent-shaped bay. For lunch, wander over to the Four Seasons Resort at Manele Bay and sit poolside at the Ocean Grill, or else head to the resort's Challenge at Manele Clubhouse. In the afternoon, plan a nap or try your hand at some crafts at the Lanai Art Center.
Day 4: Hiking (or Driving) the Munro Trail
If it has not been raining and the ground is dry, do a little exploring. The adventurous can spend the day (plan on at least 7 hr.) climbing to the top of Lanai on the Munro Trail. The not so adventurous can take a four-wheel-drive vehicle. Soak in a hot tub on your return.
Day 5: Enjoying a Day on the Water
Ring up Trilogy Lanai Ocean Sports and book a sailing/snorkeling, whale-watching, or scuba trip.
Day 6: Kayaking or Horseback Riding, Followed by a Trip Back in Time
If you can't get enough time on the water, plan a morning kayaking tour with Trilogy Lanai Ocean Sports. A picnic lunch is included. Horse lovers should arrange a tour of Lanai through the Stables at Koele. In the afternoon, take a four-wheel-drive vehicle to the historic ruins of the old Kaunolu Village, on the southwestern side of the island.
Day 7: Biking & Shopping
The best way to get around the tiny village of Lanai City is via bicycle. Rent one from the Four Seasons Resort Lanai, The Lodge at Koele, and ride (downhill) into town. Lanai City has some terrific boutiques that you'll find nowhere else.