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. As with 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. The snorkeling is terrific. It's generally safe for swimming. 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 directions 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 Fresco. In the afternoon, plan a nap or try your hand at some island 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 (allow 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: Horseback Riding & Taking a Trip Back in Time

Saddle up. Horse lovers should arrange a tour of Lanai through the Stables at Koele in the morning. Then plan a four-wheel-drive trip in the afternoon 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.

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.