Island Matchmaker: Which Hawaiian Island is Calling You?

Please welcome guest writer Roxanne Bichard from Luxury Retreats. I’m delighted with this topic, since I’m planning to spend my upcoming birthday in Hawaii!

Visiting America’s 50th state presents a dilemma. With its fascinating culture, soft, sandy beaches, rainforests and volcanic landscape, it’s easy to be paralyzed by an overwhelming desire to see everything Hawaii has to offer. The problem is Hawaii’s attractions are scattered over 6 separate islands. What’s a traveler to do?

Though you could try packing all of them into one vacation, it might be time consuming, stressful, and you’d miss out on the whole reason many people come to these islands… to relax! Believe us, even if you only see one island, you will not run out of places to see and things to do.

Here’s a breakdown of each island. Which one do you think is your perfect match?

Hawaii Island (The Big Island)

Volcano Haleakala

The lowdown: The “hot spot” of the Hawaiian archipelago, Hawaii Island is home to the most active volcano currently on earth, Kilauea. This island is the only one releasing a continuous flow of lava that trickles down into the sea, producing its famous black sand beaches. The largest of the Hawaiian Islands, it is also home to the state’s largest national park: Hawaii Volcanoes National Park.


  • The site where Captain James Cook first stepped foot on the island (and was later killed in a battle with Hawaiians!)
  • Puuhonua o Honaunau National Historical Park, a refuge for early Hawaiian lawbreakers
  • The traditional Hawaiian cowboys (paniolo) of the Waimea pastures
  • The distinguished Kona region, famous for producing remarkably smooth coffee. Fun fact: Hawaii is the only state in the U.S. with growing conditions suitable for coffee. Just one more thing to love!

Advantages: You won’t see flowing lava on any of the other islands. Being on the Big Island is seeing creation in motion, as the more lava it produces, the more the island grows.

Disadvatages: For some, big can mean overwhelming, and renting a car may be your only option for getting around.

The Verdict:  Will appeal to curious travelers looking for adventure.


Maui Beach

The lowdown: The second largest of the Hawaiian Islands, Maui is renowned for its stunning beaches. Less crowded than Oahu, Maui is also famous for its romantic sunsets and home to a dormant volcano, Mount Haleakala. In the winter months, it is one of the best places to whale watch as thousands of humpback whales migrate to its warm, crystalline waters. Small, eclectic towns where you can catch a luau or do some shopping or dining give this island great versatility.


  • The Iao Needle, a natural rock pinnacle rising from the spectacular Iao Valley
  • The Pools of Oheo, tiered natural pools fed by cascading waterfalls
  • Lahaina, a unique, energetic harbor town full of fun activities
  • Any beach. Seriously, they’re all pretty spectacular! Ka’anapli, however, is a favorite

Advantages: Maui County also encompasses the small neighboring islands of Lanai and Molokai, the most unspoiled of the Hawaiian Islands. A great place to get away from the crowds, Maui gives you the option of daytrips with easy access by ferry.

Disadvantages: Maui is generally more expensive than the other islands, as much of the goods are shipped through Oahu.

The Verdict: Will appeal to travelers who are looking for a laid-back, romantic vacation.


surf lesson on oahu

The lowdown: The most popular choice among visitors, Oahu is famous for its North shore surfing hotspots such as Sunset Beach and the Banzai Pipeline. As the major hub of Hawaii, it is home to the state’s capital, the vibrant city of Honolulu. Oahu has some of the best entertainment and nightlife on the Hawaiian Islands. Full of variety, Oahu offers a more metropolitan experience of paradise.


  • Hanauma Bay, a Marine Life Conservation District abounding with sea turtles
  • Waikiki Beach, a mecca of surf culture and home of the legendary Wakiki Beach Boys
  • Pearl Harbour, the site of the aerial attack that drove the U.S into WW2
  • Diamond Head, a volcanic tuff cone recognized as a signature symbol of Hawaii

Advantages: Hawaii’s major airport is located on Oahu (Honolulu International Airport), making it the main entry point for most of Hawaii’s visitors. This island has extensive shuttles, bus tours and public transportation that make getting around easy.

Disadvantages: Oahu is definitely Hawaii’s most popular island for tourists, making it crowded in certain areas. It may not be suitable for those who want a remote getaway.

The Verdict: Will appeal to travelers who are looking for excitement and like to be right in the center of the action.


Kauai mountain

The lowdown: Nicknamed “the garden isle,” Kauai is Hawaii’s most lush, green island with truly awe-inspiring scenery. As Hawaii’s oldest island, it has had time to grow some of the most amazing rainforests and tropical flora. The scent of tropical flowers permeates the air and the dazzling peaks and valleys are pure eye candy. Probably one of the greatest hiking and kayaking destinations you’ll find anywhere, it also has nice swimming and snorkeling beaches and a variety of luau venues.


  • The Waimea Canyon, also known as “The Grand Canyon of the Pacific”
  • The towering sea cliffs of the Na Pali Coast
  • Wailua Falls, a breathtaking 80-ft waterfall
  • The historic town of Hanalei, brimming with art and fields of taro

Advantages: Kauai is less developed and quieter than the other main islands, giving its guests the feeling of being away from it all.

Disadvantages: It is known for having some of the most frequent showers of the Hawaiian Islands (though they are usually short-lived).

The Verdict: Will appeal to nature lovers who want to appreciate timeless tropical scenery.

We hope this gives you a better idea of what to expect from each of Hawaii’s Islands, and helps you make up your mind as to which one is compatible with your personality. If you’re still torn, don’t worry—you can’t go wrong no matter which island you pick. The main islands all boast fabulous luxury Hawaii vacation rentals that do anything but disappoint! You can bet on the fact that no matter which island you end up on, it’ll feel like paradise.

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