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Plan a Hawaii Trip: The Ultimate Guide

plan hawaii trip

So you’ve decided to visit Hawaii. Congratulations!! Just a 6 hour flight from California, Hawaii often came up as a vacation option while I lived in San Francisco. It’s one of my favorite places to visit, and I’m so excited you’ve decided on Hawaii as your next destination. To prepare you for an unforgettable trip, here are some tips on planning a trip Hawaii trip.

Table of Contents

Which Hawaiian Island Should I Visit?

plan hawaii trip
Mango Farm Airbnb

There are six major islands in Hawaii: Oahu, Maui, Big Island, Kauai, Molokai and Lanai. I’ve been to three of these and I can say they all offer something quite different. So how do you decide which island to visit? Here’s a quick guide on what each island is known for, both from my personal experience and from research, to help you decide.


Oahu is home to Honolulu, the capital of Hawaii. Naturally, the island is more bustling, and the most city-like of the six islands. If you tend to like traveling to cities, Oahu is a good place to start with. You get the best of both worlds – the people, nightlife, and some of the world’s most beautiful beaches and water activities.


camp olowalu maui
Camp Olowalu, Maui

Maui is a little more quiet than Oahu, but there’s still fine dining opportunities and a good deal of night life (think live music that involves the sound of a ukelele). Maui is also home to one of the most famous scenic drives, Road to Hana. With more than 80 accessible beaches, it’s one of the best places in the world to learn how to surf.

To learn more about the best things to do in Maui, check out my 5-day Maui itinerary.

Big Island

volcanoes national park
Volcanoes National Park, Big Island

Big Island, also known as the island of Hawai’i, is even more nature-y than Maui. The island is known for its volcanoes, lush rainforest-like scenery, and as the home of Hawaii’s highest peak, Mauna Kea. Whether you’re an outdoor lover or someone who’s just beginning to explore the outdoors, Big Island is sure to wow you. Last but not least, Big Island is home to the world famous Kona coffee. There’s tons to look forward to while visiting Hawaii’s largest island.

I captured all the best things to do on Big Island in this 7-day Big Island itinerary. Enjoy!


You may have noticed a theme here. I compare the Hawaiian islands based on the ratio of nature-t- city activities. So where does Kauai sit on this spectrum? While this is one of the islands I haven’t visited personally, I’ve heard its nature-to-city ratio is close to Big Island’s. In fact, Kauai is nicknamed “the Garden Isle,” and its surface is mostly covered by a tropical rainforest.


Two popular destinations on Molokai are Kalaupapa National Historical Park and Papohaku Beach. A high percentage of the Molokai population are of Hawaiian ancestry. Stepping foot on this island will help you experience Hawaii in its truest, more local form.


People visit Lanai for its world-class resorts and golf. Similar yet different enough from the rest of the Hawaiian islands, Lanai is another place to explore nature both on land, in the mountains and under the Ocean.

Best Time to Visit Hawaii

Hawaii gets phenomenal weather year-round, never going lower than 65 degrees or higher than 90 degrees Farenheit (at normal altitudes).

best time to visit hawaii

But if you are looking to experience the PERFECT weather in Hawaii, I’d say May-July is probably the best time. During these months, Hawaii hasn’t reached peak heat yet (which by the way, is still pretty good weather), and more importantly, rain season hasn’t started.

The below graph shows roughly when it rains in Hawaii year-round and you can see that while the temperature never gets too unbearable, you could run into rainy weather if you travel to Hawaii in months outside of Apr – Sep.

Average Rainfall for Honolulu, Hawaii

Things to Do in Hawaii

heavenly coffee farm big island
Heavenly Coffee Farm, Big Island

Now that you’ve decided on an island to visit and hopefully a date for your trip, it’s time to plan your activities for Hawaii. If you’re visiting Big Island or Maui, I’ve got a few guides to get you started:

For other islands, I recommend starting your research on the Go Hawaii website.

Things to Pack for a Hawaii Trip

blue travel luggage
Photo by Craig Adderley on

With an island (or two booked), a plane ticket, and list of thing to do on your Hawaii trip, it’s time to plan your outfits for Hawaii. These five pieces are not the ONLY things you should pack for Hawaii, but they are things you can’t leave out of your Hawaii wardrobe.

Plan the Ultimate Hawaii Trip

Whether this is your first time visiting Hawaii or you’re looking to one-up your previous trip to the beautiful island(s), use this guide as a starting point to plan your Hawaii trip. Once you’ve identified which island or islands you want to visit, planning the rest only gets easier. After reading through this post, what island do you want to visit most? Let me know in the comments below!

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