How to choose the right Hawaiian island for your vacation

Published Date: January 6, 2023

Aerial of Hawaii
When it comes to a Hawaiian vacation, can you really go wrong? In short, no, but Hawaii’s different islands appeal to different types of travelers. Whether you’re looking for luxury resorts or unspoiled wilderness, active adventures or rest and relaxation, the six biggest islands in Hawaii have plenty to offer. Read our rundown, designed to help you identify the perfect island paradise for you. 

Kauai: The Garden Isle 

Bursting with natural beauty and offering a laid-back lifestyle, Kauai is the oldest of the archipelago’s main islands, the result of volcanic overflow some 5.1 million years ago. Kauai has an incredible diversity of landscapes, from the beautiful Waimea Canyon (the “Grand Canyon of the Pacific'') to unspoiled beaches and Mount Waialeale, the planet’s wettest spot, averaging 451 inches of rain each year. The south side of the island is popular with sunseekers, who flock to Poipu Beach and the area’s many restaurants, shops and amenities. The north shore of Kauai is home to high-end resorts and incredible beauty. The eastern coast, affectionately called the Coconut Coast, is popular with budget travelers and those who want a centrally located home base for exploring the island. No matter where you unpack your bags, Kauai is built for discovery, with ample hiking trails, botanical gardens and jaw-dropping Wailua Falls — easily Kauai’s most recognizable landmark.  

Oahu: The Gathering Place

Oahu is home to 80% of Hawaii’s population and the capital city of Honolulu. Oahu is a popular tourist destination for all kinds of reasons. Not only can you get there via a direct flight from many U.S. mainland cities, but it has a little bit of everything: big-city fun, gorgeous beaches, historical sites and an incredible surf culture. The vast majority of visitors to Oahu stay in the Waikiki area, where large hotels dot the coastline of this world-famous beach. Travelers looking to bypass crowds often head toward the North Shore, Ko Olina and Turtle Bay. There’s so much to see and do on Oahu, you may just be tempted to leave your beach chair and explore. Watching world-class surfers battle the waves on the famous North Shore, sampling the incredible local food scene and learning about WWII history at the Pearl Harbor National Memorial are all great ways to spend a day. 

Moloka’i: The Friendly Isle 

Visitors who want to avoid crowded beaches and large resorts may find their perfect island paradise in Moloka’i. The island is only 38 miles long and 10 miles wide, with its largest town, Kaunakakai, boasting a population of just 3,000. Moloka’i is the least visited main island of Hawaii, and visitors aren’t typical tourists. Moloka’i is a wonderful place to really immerse yourself in natural beauty and warm culture. Many visitors volunteer at farms, stay with families and simply observe everyday life on this rugged island.  

Lanai: The Pineapple Island 

A truly off-the-beaten-path travel destination, the small island of Lanai is an exercise in opposites. For example, only about 30 miles of the island’s roads are paved, yet 97% of the island is owned by billionaire Larry Ellison, and you’ll find two luxury resorts and championship golf. Lanai is called the Pineapple Island because it was owned during most of the 20th century by the Dole family, who used it to expand their pineapple farming empire. Many of the pineapple fields are gone, and ample exploration awaits. Four-wheeling is a way of life for locals and visitors. Hop in a Jeep and head out, exploring until you find your own private beach. 

Maui: The Valley Isle 

Maui is the second-most visited island in the archipelago, after Oahu, and it’s easy to see why. Maui is known for its world-class beaches, incredible whale watching and serious tourist amenities. Whether you want to watch the sun rise from the top of the dormant Haleakala volcano, attend a luau, savor fresh seafood and ocean views, golf at a championship course or drive the incredible Hana Highway along the rugged coastline, Maui has no shortage of incredible experiences. No wonder people say “Maui no ka oi” — “Maui is the best.” Maui is also known as a great snorkeling destination, thanks to the Molokini atoll a few miles offshore. Take a tour to the crescent-shaped island and experience what it’s like to snorkel in an extinct volcanic caldera. 

Hawaii: The Orchid Isle 

Commonly known as the Big Island, the island called Hawaii is bigger than all the others combined, and it boasts an incredible diversity of landscapes, from the active Kilauea volcano to rainforests to snow-dusted mountains. The island has six main regions: Kohala, Kona, Kau, the Hamakua Coast, Hilo and Puna. Most visitors stay in the western Kailua-Kona region, drawn by its wonderful weather, great restaurants and shopping, and range of accommodations. On the other side of the island you’ll find Hilo (home to the Hawaii Tropical Botanical Garden) and Puna, the island’s easternmost tip. At Hawaii Volcanoes National Park, you’ll see the world’s largest volcano, Mauna Loa, elevation 13,677 feet. The park is simply begging to be explored, with an incredible 333,000 acres of lush scenery, lava tubes, volcanic activity and more. The Big Island’s beaches are also gorgeous, and vary dramatically from one to the next. Hike to the green sand beach of Papakolea, visit the black sand beach of Punalu’u and strap on a snorkel mask to spot green sea turtles in Kahalu’u Bay. 

Find your island getaway  

Which island will you fall in love with? No matter which you choose, there’s so much to explore, and a second home in Hawaii puts it all within reach. Say aloha to your new vacation retreat!

Jen Headshot

Jen Lyons


  • Share this post:

Don't miss out

The best homes sell fast. See the latest listings, inspiring second homes and buying tips.

Want to chat? Contact us.