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Which is the best Hawaii island for my family vacation? Confusing, I admit. It is very confusing. With the five main Hawaiian Islands available for selection, determining which one best suits you can be difficult, and the fear of missing out, the FOMO is real!

There is no best. Simple. All of the major islands of Hawaii have just about everything that gives an island its appeal – calming beaches, soft white sand, lush vegetation, lots of cultural sites, and lots of fun in the sun for families. But they also offer different things. Your choice of an island would depend on what you hope to get out of it and how your family would want to spend the time on the island.

The Best Hawaii Island for a Family Vacation to Avoid FOMO

Maui, Hawaii

Maui is home to some of the world’s best beaches. Does your family like to play in the water and lounge on the beach most of the vacation? Then choose Maui. It offers everything that makes Hawaii so special. Golden sunny beaches, majestic whales in the winter, a volcano, and relaxing resorts. Maui is your ideal resting place. If your vacation is meant to be a peaceful, relaxing time, visit Maui. Maui is also a great place if you are visiting with your family. There is also no shortage of things to do from snorkeling and swimming with the turtles, to hiking to the volcanoes and experiencing the luau.

How to pick the best Hawaii Island for a family vacation? FOMO is high and you don't want to make a mistake. Makena Big Beach, Maui

Makena Big Beach, Maui

Kauai, Hawaii

Kauai, the Garden Isle, is the oldest island of the Hawaiian chain. If you wish to enjoy nature in its pure, romantic form, Kauai is the island for you. The grand waterfalls, remarkable coastal trails, unblemished beaches, lush green cliffs, and colorful gardens combine to make Kauai a place to love. Throw in a hiking visit to the Grand Canyon of the Pacific, and your Hawaii vacation is complete.

The best Hawaii Island for a Family Vacation, Napali Coast, Kauai, Hawaii

Napali Coast, Kauai

Oahu, Hawaii

Home to Hawaii’s largest city, the capital city of Honolulu, Oahu is one of the most vibrant islands in the Hawaiian chain. Oahu has just about everything you’d expect from a modern city. A vibrant nightlife, natural wonders, historic feel, and a bustling entertainment industry, you’ll see it all. With all of its high-rise buildings, luxury shops, bustling restaurants, and nightclubs, you’d simply be enjoying a vacation in seemingly familiar surroundings. It’s impossible to miss a visit to the iconic Waikiki, one of the world’s most famous beaches.

The Best Hawaii Island for a Family Vacation to Avoid FOMO

Waikiki Beach, Honolulu, Oahu

The Big Island, Hawaii

The last of Hawaii’s biggest, most popular islands. The Big Island is the largest of the Hawaiian island chain. It is big, literally, bigger than all of Hawaii’s other islands when combined. A vacation in Big Island is one you wouldn’t forget in a hurry, and there is no shortage of activities to keep you busy. It is an island with history. Stories of kings, gods, and traditions are sure to grace your stay. Stunning waterfalls, untouched rainforests, silvery beaches, an active volcano, and snow-capped mountains. What’s not to love?

How to pick the best Hawaii Island for a family vacation? FOMO is high and you don't want to make a mistake. Punaluu, Black Sand Beach, Big Island, Hawaii

Punaluu, Black Sand Beach, Big Island, Hawaii

Molokai, Hawaii

If you want to enjoy the unspoiled and authentic Hawaii, Molokai is the place for you. Much like (and even more than) the Big Island, Molokai preserves a strong sense of history. It is home to the epic Kalaupapa Peninsula (site of a prominent leper colony). Of course, it doesn’t miss the ideals of an island, either, with long stretches of beaches and grassy mountains available for your enjoyment. In keeping with the local style, it’s not uncommon to find resorts with secluded cottages and condos.

How to pick the best Hawaii Island for a family vacation? FOMO is high and you don't want to make a mistake.  Kawela Beach Park, Molokai, Hawaii

Kawela Beach Park, Molokai, Hawaii

Indeed, visiting Hawaii is an awesome way to spend your family vacation. Worried that you don’t have enough time to visit all of the major islands? Why not spend your time exploring just one. By spending time on a single island, you immerse yourself in its culture and its people. On your next visit, explore yet another. The difference is stunning. The beaches, history, and people are sure to keep you entertained. Every island has something for everyone.

Are you planning your family vacation to Hawaii on your own? Then you’re missing out on expert help and our seamless execution of the most complex itineraries.

Couple at the beach

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For an idea on where to go in 2023, check out one of our sample itineraries here

Here are some “extras” I can help you with to make your travel experience seamless.
Want to arrange for a special anniversary dinner, bespoke champagne tasting, catamaran day trip, or a private, pre-opening museum tour for your family? You got it.
Private, luxury transfers: relax and enjoy your vacation without worrying about driving in a foreign destination after a long transatlantic flight. We can arrange for a luxury car with drivers that have knowledge of each destination.
Unmatched culinary experiences: Looking for a reservation at a specific Michelin-star restaurant or a private walking food tour, wine tasting, or whiskey experience? We can help.
A digital itinerary on an app that’s available even when your phone is offline. The app includes all activities, vouchers, and confirmations. You never have to worry about losing your printed travel documents again.

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