Hawaii is a unique and incredible part of the United States. It’s so unlike the rest of North America that it feels like a foreign country…even to Americans! The island state is becoming increasingly more of a hot spot for tourism and is the perfect getaway for a long weekend, family vacation, nature exploration, honeymoon, or beach lazing, leaving people with the question: “Which Hawaiian Island should I go to?”! Well, I’m here to help!

The history and culture of Hawaii and its people differs from that of the mainland US drastically and can teach us all a thing or two about a slower pace of life.

The first time I visited the islands was for a wedding of a family member. Then I was hooked. What I had previously mistaken as “a more expensive Mexico” blew me away with its food, culture, beaches and surprising affordability. Since that first trip, I made it a point to go back a few times already & a goal to visit every island (that foreigners are allowed). Here is an easy break down of what to expect from three of the major islands in the archipelago.

A quick heads up: this post may contain a few affiliate links. This just means that (at no additional cost to you) when you click them, I will be able to continue to create more content to help you travel naturally! For more info about it, see my Affiliate Disclaimer. Thanks for your support!

Want to jump to a specific Island? Go to OahuKauaiThe Big Island by clicking on their names.

Which Hawaiian Island Should I go to: Oahu

Which Hawiian Island is the most tourist-friendly?:


Oahu is one of the top rated islands and is a hotspot for international tourists. With so many options of actvities, restaurants, and places to stay, planning for a trip to Oahu can feel a bit overwhelming. However, once you are basking in the sun (with your new, natural sunscreen) on a beautiful beach, your stress will melt away & this easy-to-navigate island will prove to be a great choice. Oahu is a fantastic choice for families or those just dipping their toes into the world of Island travel.

Best place to eat: The Sunrise Shack. Coffee, smoothie bowls, fresh & local fruit, across from the beach with an adorable and brightly painted outdoor seating area.

Where to stay: Castle Waikiki Grand Hotel. Although the name sounds expensive, they often run deals that will have you spending about the same as you would for a hostel in the same city. Simple rooms but great amenities, airport shuttle, and walking distance to restaurants, beaches, nightlife and shops.

What to do: Swim & snorkle with sea turtles, horseback the Jurassic Park filming location, drive to viewpoints, hike one of many trails, experience the nightlife of the big city, learn from the Pearl Harbor museum, or book from several options of adventure, foodie and high class tours.

Pro tip: Every Friday evening, Waikiki hotel, right on the beach, puts on a beautiful firework display. There are often fire dancers & musicians busking on the sand. AND, because it’s a public space, it’s completely free to watch & you can bring your own snacks and picnic under the glow of fireworks & moonlight.

Find a few more amazing Oahu activities here:

Pros of Oahu:

+ Because there so many accessible & sandy beaches, it’s not too difficult to find a quiet spot.

+ Lots of history on the island & viewpoints with plaques to explain it all.

Cons of Oahu:

– Honolulu (the major city) is riddled with foreign tourists.

– Getting around outside of the city without a car can be a bit tricky and time consuming.

Which Hawaiian Island is best for exploring nature?:

Which Hawaiian Island should I go to: Kauai


If nature exploration and adventure are at the top of your priority list when looking into the Hawaiian Islands, Kauai is certainly not to be missed. Although the options may seem a bit limited as a result of less tourism, the authentic charm & laid back lifestyle of the island will give you a sense of the real Hawaii and its local culture! I highly recommend Kauai for a couples getaway or nature lovers reset destination. Psst…this one is my top choice to return to.

Best place to eat: Kalapaki Joes. This is the place you imagine when you daydream about restaurants in Hawaii. Helpful staff willing to crack a joke, amazing blended cocktails, traditional plate lunches (including loco moco-YUM!), local beef and an unbeatable location.

Pro tip: When you find the Safeway in Kapa’a, look just to the right of it (in the same complex) and find the best ice cream place in all of the Hawaiian islands (imho)!

Where to stay: Waipouli Resort. Okay, i’ll admit that I almost NEVER suggest a resort, but this one has it all. A lazy river pool with water slides, full kitchen in-room, private beach access, and the location is unbeatable. Directly across from any store you could need and a short walk to local markets, food trucks, and beaches! Perfect for families or big groups!

What to do: Choose from one of the near endless options of hikes, snorkel the reef, surf (check out Tamba Surf Shack for rentals and lessons), shark nest beach, drive around *most of* the island in just a few hours, sip cocktails on the sand, tour the Na Pali coast, & have a chat with locals.

*The reason you can’t drive alllll the way around the island is because a section of Kauai is unreachable by car. (COOL!) This part is the Na Pali Coast State Wilderness Park and is protected by the Dept. of Land & Natural Resources. It’s not to say you can’t explore & appreciate this area, and there are a few amazing ways to see it:

Click the buttons above to learn more about each adventure.

Insider tip: Smith Family Luau! Don’t let the name fool you, this is an authentic and locally owned/operated attraction. This was absolutely one of the major highlights of our trip and includes one of the best Hawaiian meals you can find, bottomless drinks, a cultural show, exploration of the local garden, and a historical presentation! Go to their website for more info.

Check out these book now, pay later activities:

Pros of Kauai:

+Lot’s of seemingly untouched nature to explore.

+ Easy to drive the *near* entirety of the island in one day.

Cons of Kauai:

-With less accommodation than the other islands, you might be spending a little more per night.

-Limited nightlife and less “touristy” options may leave you feeling a little secluded.

Which Hawaiian Island should I go to?-Oahu

Which Hawaiian Island is best for a road trip?:

The Big Island

Being the biggest in the chain, this Island has a lot to live up to. And boy, does it! The volcanic activity makes for some exciting national park visits as well as unbeatable black sand beaches. Lush forests offer unmatched greenery and small towns hold tightly to the indigenous Hawaiian charm. The Big Island is perfect for a friends trip and activity enthusiasts alike.

Best place to eat: Pineapples open air restaurant & bar. Live music on weekends, happy hour & drinks straight out of a pineapple!

Insider tip: Be sure to stop at Punalu’u Bakeshop on the South side for a few, traditional Malasadas. Trust me.

Where to stay: Airbnb was our favored option. Although there are several resorts (& about 90% of the island’s accommodation) on the Kona side of the island, if you’re looking for a more ‘live-like-a-local’ feel, check out some of the amazing airbnbs the Hilo side has to offer!

What to do: Volcanoes Natl Park, Hikes to waterfalls, Cave exploring, snorkling, surfing, resorts on Kona side, farmer’s market in Hilo, local cafes scattered about, drive the entire island in a day, choose from one of the many tour options.

Looking for a few tours to explore The Big Island?

Bonus tip: The Kona side of the Island caters a lot more to tourists. Most of the resorts are located on this side, as well as major shopping centers, restaurants, and activity/tour companies. The Hilo side of the island is significantly more local, less touched by tourism. Each side is unforgettable in its own way & worth visiting.

Note: I always recommend getting the more local, authentic feel of a new place, but please be respectful of the Hawaiian locals & obey the “locals only beach” signs when looking for a spot to picnic.

Pros of The Big Island

+ Two very different sides of the Island cause two different experiences.

+ Airbnbs are scattered all over the Island, making it easy to find accommodation anywhere.

Cons of The Big Island

– You will need a car if you want to see all of it.

– Some secluded beaches and hikes require 4wd to get to.

Packing for which hawaiian island

A few must-pack items:

Books to help you plan & decide which Hawaiian island explore:

Other articles you might like:

Essential Travel Gear for this year's adventures
How to choose the prefect luggage

There's always more to explore: