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Planning a Trip to Hawaii: The Ultimate Guide

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Updated: Feb 26th, 2024

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 to Hawaii.

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 quieter than Oahu, but there’s still fine dining opportunities and a good deal of night life (think live music that involves lots of ukelele playing). 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

plan a trip to hawaii 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. Big Island is also 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. Many of my friends have called this the best island they’ve visited in Hawaii!


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

plan best time to visit hawaii weather by month

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

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 image shows roughly when it rains in Hawaii year-round (based on Honolulu) 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.

Top 10 Must-Dos 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. Here are my top ten must-dos when visiting the Hawaiian islands.

1. Take a Surfing Lesson

I took my first surfing lesson in Maui, and I wouldn’t have done it anywhere else. I picked an instructor that had a lot of positive reviews and a class that would take place on a beach known for beginner-friendly waves.

2. Eat Classic Hawaiian Grubs

I’m talking spam musubi, tropical fruits, acai bowls, macadamia-crusted mahi mahi, and mai tais. The food is so good on Hawaii, you’ll want to do some outdoor activities to balance out the calorie intake.

3. Visit Volcanoes National Park

Not to bias you, but Big Island is my favorite of the Hawaiian islands, and that’s partially due to the fact that Volcanoes National Park is there. Imagine seeing traces of a lava explosion that happened in the past while driving by the Pacific Ocean. That can be only done at Volcanoes National Park on Big Island!

4. Try Kona Coffee

Kona coffee is made with beans from the volcanic soil on Big Island. Not only will you find coffee shops made from Kona beans sprinkled throughout the island, you’ll also be able to visit a coffee farm and learn all about how coffee makers turn coffee plants into the drinks many of us love today.

5. Go Snorkeling

Snorkeling is one of the best things to do in Hawaii. And if surfing isn’t for you, but you still want to spend some time in the water, snorkeling can be a great alternative.

Molokai is the longest fringing reef in Hawaii and one of the best places to go snorkeling as it attracts all kinds of sea mammals. You can fly onto the island from the other Hawaiian islands or get there by boat.

If you’re visiting Maui, there are also many tours going to the Molokini Creater. It takes just 30 minutes to get there by boat and many tours make a whole experience out of it by offering beverages on the boat and giving you a history of the crater.

6. Attend a Luau

Have you even been to Hawaii if you haven’t attended a luau? The ultimate celebrating, a luau is a feast featuring traditional performances, a buffet normally, and beachfront seating. It’s almost like attending a wedding!

7. Take the Road to Hana

The Road to Hana is a famous route to take while visiting Maui, and one of the best things to do in Hawaii. It stretches 64 miles across the eastern side of the island and the whole route will take the whole day to get through. You’ll see incredible scenery, enjoy locally made banana bread, and have the opportunity to dip your toes into hidden waterfalls.

8. Watch the Sunrise at Halaekala

My friend and I woke up at 4am to drive to the peak of Halaekala in order to witness the impressive sunrise. Unfortunately it was so foggy that we didn’t see much, but I’m sure if we went on a better day it would’ve been incredible!

9. Go Stargazing at Mauna Kea

Possibly one of the most romantic (and chilly) things you’ll do in Hawaii is going stargazing at the highest peak in Hawaii, Mauna Kea.

10. Night Dive with Manta Rays

And last but not least, this is the activity that will be a good conversation starter when you return to work from your trip to Hawaii. You can go diving (or snorkeling) at night in order and have manta rays swim around you. One even brushed me!! It’s such a cool and unique experience and you’ll learn so much about manta rays and how lovable they are after the excursion.

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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