Best Islands to Visit in Hawaii for the First Time

Best Islands to Visit in Hawaii for the First Time

Where should couples go in Hawaii for the first time?

Each island of Hawaii has its own individual charm, unique landscape, culture, history and a variety of attractions. Those who are visiting this paradise state for the first time will but naturally daydream of swaying palms, azure blue waters and a relaxed vibe, which is probably right.

The issue is with so many gems strewn across Hawaii, planning to see the right ones can become a daunting task. Luckily for you, this guide will lead you to only those hotspots, which will make your premier trip to the Aloha state full of joy, providing you keep ample time aside to visit them all.


beachfront with palm trees and blue ocean water

The first island you should choose for your trip to Hawaii should be based on the direct flight connections available from your country of origin.

O’ahu, being a popular island is most likely to fit the bill, especially if you are traveling with little ones. The majority of the population stays here and is also the site of the state capital Honolulu.

For an urban feel, exciting nightlife and high end shopping, this is the place to land for first timers. Practically all the international flights land first on O’ahu before connecting to other islands.

With a plethora of sites to explore, one can easily spend the entire holiday exploring just the island of O’ahu. Surfing, stand up paddle boarding and kayaking are some of the best ways to explore the east side.

The surfing spectacles are a sight to behold during the winter months at the world famous Bonsai Pipeline and Waimea Bay where the conditions are favorable for surfers.

Located on the south side, Waikiki and Honolulu are top entertainment centers as well as the home to major cultural and historical attractions.


whale jumping out the ocean water

Nicknamed ‘The Valley Isle’ after the sacred Iao Valley, Maui is the second largest of all the islands in Hawaii and home to some of the best beaches in the world.

Additionally, during the winter months, Maui offers exciting whale watching opportunities from Lahaina Town. Ideal for honeymooners and families with younger children as you do not need transport to access any of the restaurants and the popular beaches.

Staying in Lahaina or Kaanapali will give plenty of options of activities, just a stroll away.

Most first time visitors travel to Maui because of its diversity. The south side of the island tends to be quieter with Oneloa Beach a perfect spot for snorkeling and swimming.

The Road to Hana is the top draw on the east side as it boasts of some of the most incredible views ranging from rainforests to dramatic cliffs and cascading waterfalls like the Seven Sacred Pools, a series of waterfalls inside the Haleakala National Park.


beachfront resort with palm trees and greenery

This is the oldest and least populated of all islands in Hawaii and is also referred to as the Garden Island.

The beautiful landscape and the high end resorts makes it an ideal getaway for those seeking a little bit of peace and tranquility. The lush green mountain sides present a picture of surreal natural beauty that cannot be found anywhere in the state.

The southern side of Kauai has some exceptional snorkeling sites and secluded white sand beaches.

The old town of Koloa is home to the sugar cane mills, the oldest industry of the island.

Kauai’s largest town, Hanapepe, has an amazing array of art galleries, boutiques and restaurants. As you dine you can watch local artists trying their hand at painting pottery and tiles.

First timers, who want a bit of everything should visit the east side as it is centrally located and near all the shores of the island.


beachfront with palm trees

This fifth largest island of Hawaii is just 38 miles in length and 10 miles wide at its largest point. True to its island roots, Moloka’i has the longest and continuous fringing reef and some of the tallest sea cliffs in the world.

Thanks to the majority of the population who are native Hawaiians, the island has managed to preserve its rural way of life even till today. From walking on cliff edges at the Kalaupapa National Historical Park to discovering the many attractions of Papohaku Beach, Moloka’i is the only destination in Hawaii where you come face to face with the past.

While most of Moloka’i is rocky outcrop, the waters around here are the richest in the Pacific for divers and anglers.

Visitors can hop on a charter fishing boat from Kaunakai or go whale watching at Kaloni channel. Hawaiian monk seals and schools of rainbow fish make this place a live aquarium just a few meters below the surface of the ocean.


sunset beachfront with pink flowers and palm trees and green landscape

The smallest inhabited island in Hawaii, Lanai has plenty of enticement for first time visitors.

While at one end are some of the most luxurious resorts the other side is a mecca for exploring off beat treasures. Lanai has eighteen miles of coastline dotted with remote beaches like the Hulopoe Beach Park and Puu Pehe a short walk away.

Hawaiian Islands are often associated with the names of the persons who ruled them in the past. Lanai’s isolation and tranquility makes it a leading honeymoon destination.

As you sunbathe, snorkel and watch the dolphins at Hulopoe Bay, you will feel the island was just made for two people. Go on a 4×4 adventure ride to North Lanai and discover miles and miles of blissful and empty coastline perfect for sunbathing and beachcombing.

One of the most important advice for first time visitors to Hawaii is to set a budget and strictly stick to it. The flights, accommodation, travel between islands and food can easily rack up a hefty amount in no time at all.

Once the financial aspect is taken care of, book your flight and hotel as these fluctuate very often. Inbound travel is much cheaper during the middle of the week than the weekends.

Then sit down, and use this guide to choose the best place to go to Hawaii for the first time, and you are ready to jet off with your family.

Check out these other relaxing family vacation ideas:

10 USA East Coast Beach Vacation Spots for Couples

Europe Beach Bucket List for Couples

16 Romantic Things to do in the Fall With Your Husband

If you’re wondering which island to visit on your first trip to Hawaii, this info will help you to plan a worry-free, paradise vacation with your family.

Have you visited Hawaii before? Where did you go on your first trip to Hawaii? Leave your vacation experience in the comments. We’d love to hear from you.

10 comments found

Leave comment

Your email address will not be published. Required fields are marked with *.

Skip to content